Back in 2011, my local paper asked me to review a Daughtry show. This experience shook me. The massively popular American Idol-approved band represented the worst nightmare of a listener who once worshipped the likes of Pearl Jam and Alice In Chains – not “post-grunge,” but “post-post-grunge.” Daughtry ripped off Eddie Vedder, but by way of Scott Stapp. It was like a mad scientist created club-footed, brain-dead clones of the best bands of the 1990s, and then made those clones procreate. This concert filled me with pop culture paranoia – was any of the music I grew up with actually any good?

Which is a long way of explaining why I decided to revisit the soundtrack to my high school and college years, and list my top 100 albums of the decade. It was refreshing to realize that, even seen in hindsight’s harsh, unforgiving light, a lot of the stuff I loved holds up. I’m sure nostalgia is clouding my judgment on many of these choices, but jeepers creepers, I’m only human.

So, when the biggest rock band of 2021 credits Daughtry as its main influence, I’ll have this list to come back to, and remind myself that yes, it’s still good.

100. Moxy Früvous – Bargainville (1993)

Remember how I said that thing about nostalgia just now? Well, this record’s on here largely because of it. Don’t get me wrong, Moxy Früvous was teeming with talent – a Toronto quartet of multi-instrumentalists who harmonized like a hybrid of The Beatles and The Andrews Sisters. But in concert was where the group really shone; its energy, humor, and awe-inspiring tightness made for some of the most memorable live experiences of my teenage years. Bargainville is its best album, a mix of poignant folk and quirky novelty tunes. Listening to it today does make me cringe just a bit – why, oh why, does it begin with a ballad about our dying environment (“River Valley”)? Sure, Bargainville might be an awkward mix of the self-serious and the seriously nerdy. But that’s also a dead-on description of me at 15.

99. Dr. Dre – The Chronic (1992)

If this exercise was an attempt at listing the albums I loved and obsessed over in the 1990s, The Chronic would crack the top ten for sure. I was 10 when Straight Outta Compton came out, so Dr. Dre’s solo debut was my first exposure to the lurid, hilarious and irresistible world of gangsta rap. But listening to it now is a bit of a chore – the production remains some of the best in rap history, and Snoop Doggy Dogg’s flow is unimpeachable, but so much of the lyrics are bogged down by Dre’s obsession with his own personal beefs, and frankly, his mediocre rapping ability. To quote Chris Rock: “It’s hard to drive around singing songs about ‘Easy-E can eat a big fat dick.'” Also, this might be the most misogynistic hit record of all time. The song “Bitches Ain’t Shit” is ironic, because the song is most definitely shit. Hearing this album now makes me understand why I can’t get with artists like Odd Future, despite a sound that appeals to my sensibilities – it’s a pain in the ass to have to constantly rationalize to myself why I like something. Despite all of this, I still can’t deny a genius when I hear him; The Chronic makes this list because of Dre’s production wizardry, a singular talent that would shine even brighter on the superior Doggystyle.

 

98. Lauryn Hill – The Miseducation Of Lauryn Hill (1998)

I don’t want to be one of those people who calls something like Lauryn Hill only releasing one album “tragic.” But it is a bummer. Especially when you consider the major flaw of her magnificent debut – its 77-minute running time. So much of The Miseducation of Lauryn Hill is so impressive, blurring the lines between R&B, gospel and hip hop, laying down a “neo-soul” template that few would come close to matching, brilliantly juxtaposing the bitterness of failed love with the hopes and mysteries of childbirth. Still, it’s tougher than it should be to get through the whole thing, what with the schoolroom skits, the hidden Frankie Valli cover, and the stretch of five long R&B tunes that get you from “Final Hour” to “Everything Is Everything.” One hoped that Hill’s future efforts would maintain this dizzying level of artistry, while exhibiting a stronger ability to self-edit. But that was a lot to expect, it turns out. This one’s all we have, and we should thank god for all 77 of those minutes.

 

97. Sublime – Sublime (1996)

By the time ska-punk and swing had infiltrated the mainstream in the mid-’90s, I was immersed in it. Looking back, it’s embarrassing to remember Carson Daly introducing a Reel Big Fish video in a two-tone suit, and it’s more embarrassing to remember how much I loved Reel Big Fish. But even after all this time, and all the guilt I’ve had to process, there’s no doubt in my mind –  Sublime’s third album kicks ass. And I don’t care how many frat boys in pre-torn South Carolina Gamecocks hats agree with me. Bradley Nowell’s swan song revealed him as some kind of stoner-poseur genius. He appropriated hip-hop and reggae tropes in ways that should’ve been embarrassing. He sang about tits, butts and bong loads. But his voice ached and cracked with seemingly unwarranted pathos. Were we hearing an addict struggling to hold on to the good times? Were we just hearing a super-talented guy at his peak? No matter the reason, Sublime rules, bro.

 

96. Soundgarden – Superunknown (1994)

Grunge is often credited as the genre that snuffed out hair metal, which is suspect at the very least. But it’s ironic that Soundgarden was one of these vaunted acts allegedly responsible for killing the Crüe, poisoning Poison, and slaughtering Slaughter (I’ll stop there). While it did a better job with the follow through, the band’s formula wasn’t so different from Whitesnake’s – Zeppelin-esque ambition, Sabbathy riffage and a disarmingly pretty lead singer. If you had to bet on one of those Seattle bands becoming rock stars, they were the obvious choice. And Superunknown made good on all of this critical and commercial potential, a darkly tinged arena rock album with just the right mix of killer riffs, power ballads and moody meditations. Its only misstep is “Kickstand,” an workmanlike attempt at snarling punk that just underlines how different Soundgarden was from Nirvana. But what it lacks in gut-punching attitude, Superunknown makes up for in production value. An immaculately crafted work, performed by a singer and lead guitarist at the pinnacle of their powers, this is Soundgarden realizing its destiny – to play those big-ass venues that David Coverdale and company used to pack to the gills.

 

95. Primus – Sailing The Seas Of Cheese (1991)

“As I stand in the shower/Singing opera and such/Pondering the possibility that I pull the pud too much/There’s a scent that fills the air/Is it flatus?/Just a touch/And it makes me think of you.” This, my friends, is the essence of Primus, a band that thrived on bass solos, dissonance, nasal sing-speak and songs like “Grandad’s Little Ditty,” the old-weirdo-in-the-shower vignette that my friends and I would croon to each other like it was a Perry Como ballad. It’s just one of many moments on Sailing the Seas of Cheese made to be obsessed over by strange teenage boys, on an album that should’ve aged terribly on paper. But Les Claypool, Larry LaLonde and Herb Alexander happened to be very gifted musicians, and the obtuse nerd-funk grooves they let fly on “Jerry Was A Race Car Driver,” “Is It Luck?” and “Tommy The Cat” are evergreen. The band eventually lost me with 1995’s Tales From A Punchbowl, but for the record, it wasn’t because I’d become an adult or anything – to this day, “Grandad’s Little Ditty” makes me laugh.

 

94. Tom Waits – Mule Variations (1999)

After releasing the harrowing Bone Machine in 1992, Tom Waits took a break (1994’s The Black Rider was the soundtrack to a play he wrote and began recording in 1989). When he returned seven years later, it was to introduce yet another phase of his illustrious career. Not a Swordfishtrombones-level reinvention, mind you, but a nuanced move similar to the one Bob Dylan was making at the time – an organic, nostalgic embrace of Americana. The blues always informed Waits’ sound, whether through the hotel bar piano playing of his early records or the wonky pentatonics of his ’80s avant garde period. But on Mule Variations, the style comes through with a clarity that no Waits album, before or since, has possessed. “Lowside of the Road,” “Get Behind the Mule” and “Filipino Box Spring Hog” could all be Muddy Waters covers, and ballads like “Picture In A Frame” take the 12-bar structure into achingly beautiful places. Waits also dabbles in gospel, spoken word and adult contemporary (still waiting for Rod Stewart’s cover of “Hold On”), all with the same clear-headed approach. He lets the songs do the heavy lifting here, minimizing his vocal flights of fancy and keeping the clanging percussion to a minimum. Now I happen to really like those two things, which makes Mule Variations a second-tier Waits album in my mind. One that still kicked the shit out of most of the albums released in the ’90s.

 

93. Ice Cube – AmeriKKKa’s Most Wanted (1990)

At NWA’s height, its most talented rapper broke away and went right coast, making a solo album with The Bomb Squad, the production team responsible for Public Enemy’s massive, martial sound. I was too young to know about all of this, but for rap fans at the time, it must’ve been like John Lennon joining The Rolling Stones. To top it off, AmeriKKKa’s Most Wanted delivers. Ice Cube is at his most breathtakingly volatile, charging out the gate yelling, “I’m sick of getting treated like another damn stepchild!” A simultaneous description of his falling out with NWA and the common plight of African-Americans, the song, “The N***a Ya Love To Hate,” proved Cube was up to the challenge posed by the Bomb Squad’s crackling soul thunder. Like every gangsta record from this period, Cube’s verses devolve into meathead misogyny from time to time. But the prevailing mood is righteous anger, with the ultimate goal of shining big, fat flood lights on life in Los Angeles ghettos, exposing the problem underlined by the Tom Brokaw clip that kicks of “Rollin’ Wit The Lench Mob”: “Few cared about the violence, because it didn’t affect them.”

 

92. Everything But The Girl – Temperamental (1999)

I was never more than a casual fan of electronica during its ’90s heyday, appreciating its propulsive energy and imaginative approach to sampling, but always returning to rock and hip-hop at the end of the day. But a few of these records managed to break through my stubborn listening routine, including this one, in which Everything But The Girl suggested a world of listening possibilities that I was willfully ignoring. Temperamental wasn’t like any electronica I’d heard, a mix of moody synthesizers, jazzy samples and laid-back drum loops that wasn’t meant to get anywhere close to the dance floor. Tracey Thorn’s voice floated majestically over these post-punk techno pastiches, analyzing fizzled relationships with a resigned sense of grace. It’s a beautiful soundtrack for a long bout of after-hours introspection, and while this approach was nothing new to EBTG fans (Temperamental was its 10th album), it was, and remains, an eye-opener for me.

 

91. Cracker – Kerosene Hat (1993)

Cracker doesn’t get the breathless critical raves of its contemporaries, despite Kerosene Hat being in the same alt-country ether as Uncle Tupelo’s best work. That probably has everything to do with “Low,” the huge-ass hit song that was the only way a kid like me could become aware of David Lowery’s post-Camper Van Beethoven ensemble. Despite its rootsy, Tom Petty & The Heartbreakers groove, “Low” bumped shoulders with “Heart-Shaped Box” and “Today” on radio playlists, meaning Cracker was seemingly all about the “alt,” and not about the “country.” Which just ain’t the case. Dusting off this disc has been the most pleasurable thing about this whole project so far; I’d simply forgotten how great these songs are – “Get Off This” and “Sick Of Goodbyes” join “Low” as examples of alt-country at its peak.

 

90. Cibo Matto – Stereo ★ Type A (1999)

As delightfully trippy as it was, Viva! La Woman, the first album from the duo of Miho Hatori and Yuka Honda, boasted a formula that seemed best suited to a one-off project – a band that names itself after the Italian translation for “crazy food,” and writes a bunch of weird acid-jazz songs about food. But luckily for us, instead of belaboring things, Cibo Matto expanded its artistic vision, along with its lineup, for its outstanding follow-up. Gastronomy is only a passing fancy here, with Hatori and Honda applying their distinctly strange lyrical touches to wider themes of love and cosmology. More importantly, they keep the non sequiturs to the verbal realm – Stereo ★ Type A ditches the muddier patchwork production of Viva! for widescreen accessibility. On the earwormy dance-pop of “Spoon” and “Lint Of Love,” the geek-rap of “Sci-Fi Wasabi,” and the light samba of “Stone,” Cibo Matto suddenly sounded like a group that was meant to make great records deep into the next millennium. Of course, they broke up in 2001.

 

89. Barenaked Ladies – Maybe You Should Drive (1994)

Here’s the second wonderfully talented Toronto band to appear on this list, and hindsight hasn’t been kind to either. But unlike Moxy Früvous, who was just more of a live animal, Barenaked Ladies’ oeuvre is colored by the mainstream success it experienced later in the decade – success that can mostly be attributed to one completely obnoxious single, and a handful of innocuously bland tracks released in its wake. Listening to the band’s earlier work now, I can’t help but look for evidence of the “One Week” formula everywhere (finding it all over its debut, Gordon, for the record). But Maybe You Should Drive emerges from this pop forensics investigation largely unscathed. It’s the band’s most “grown-up” album, a collection of cleverly penned, XTC-indebted pop tunes and whisper-serious ballads. Steven Page was on a roll here, contributing his classic unrequited love song “Jane,” the country-pop beauty “You Will Be Waiting,” and the charmingly unabashed novelty cut “A.” And while Ed Robertson’s groovy folk melodrama “Am I The Only One?” might not clench my heart the same way it did 18 years ago, it still has its way with me when it comes on. I selfishly wish BNL stayed down this path, instead of beginning their inexorable decline with the forced cheerfulness of Born On A Pirate Ship. They most certainly wouldn’t have hit pay dirt in that fashion, which is why I don’t manage rock bands for a living.

 

88. Arsonists – As The World Burns (1999)

As The World Burns begins with a clever nod to “A Day In The Life,” blending studio chatter with a clip of that string section burning chromatically through the octaves. The reference works, because while As The World Burns isn’t Sgt. Pepper’s, both albums share a similar goal – to off-set the expected with the occasional tripped-out detour. Arsonists gives you the adrenalized street-rap showcases you’d expect from a late-’90s Brooklyn hip-hop group, like “Backdraft” and “Shit Ain’t Sweet.” But they follow them up with “Pyromaniax,” a track that finds MCs Q-Unique and D-Stroy getting profoundly whacked over a goofy calliope loop, to the point where they’re doing a Monty Python-esque impersonation of a screaming Cockney couple (an experience that rivals dog whistles and backwards recordings in the fantastically strange department). It reminds me of a recent Wu-Tang show, where Method Man spent a good amount of time complaining about how today’s hip-hop artists have forgotten how to have fun. I’m not sure I agree with him, but listening to this album does make me see his point – we don’t hear too many records like As The World Burns these days, albums whose only goals are to stop people in their tracks, get them laughing, and keep them dancing.

 

87. Tori Amos – Boys For Pele (1996)

As a teenage boy who spent the ’90s attempting to play keyboards and pretending to not be deathly afraid of girls, I was heavy into Tori Amos. Sure, I didn’t understand much of anything she was singing about, but it was art, man. Sensitive art that showed what an amazingly sensitive man I was. As I slowly grew out of this cocoon, met my ravishing wife, and realized that few things were more insufferable than a man who hopes his CD collection will get women to like him, Amos’ records lost a bit of their magic to me. With the exception of Boys For Pele, that is. Here is everything this artist does best – shimmering waterfalls of piano and harpsichord, dramatic dynamic shifts, the occasional stone-cold groove, and lyrics that go where the flakiest lyricists fear to tread. Like any Amos album, it’s indebted to Kate Bush, but Pele has her discography’s highest percentage of original ideas, from the neo-classical piano licks of “Father Lucifer” to the grinding harpsichord riffage of “Professional Widow” and the rainy day blues of “Little Amsterdam.” And as a player, Amos is brilliant, communicating to us through her instrument, often by just letting the chords do their thing.

 

86. The Mighty Mighty Bosstones – Question The Answers (1994)

I mentioned this in my comments about Sublime earlier, but you probably didn’t read that, so I’ll say it again – I was once smitten with the mid-’90s mini-revival of ska/punk. As a quiet kid with plenty of pent-up energy, I loved these bands with seemingly boundless reserves of adrenaline, soaking up their irreverent material and catchy horn parts. But like anything that’s heavily templated, 95% of this stuff was too repetitive to make any lasting impact on my listening habits. The Mighty Mighty Bosstones are one of the few artists that survived this ska-pocalypse; they were a party band, yes, but one with a little depth and nuance beneath all the fun hooks. In my view, they were able to do what no other group could – staying comfortably within the restrictive ska-punk guidelines (horn section part, sped-up reggae verse, thrashy punk chorus, repeat) while crafting a sound that’s completely their own. Question The Answers was the zenith of the group’s rowdy-yet-accessible sound, combining “singer” Dicky Barrett’s Tom Waits-meets-Henry Rollins growl with some of the decade’s most skillfully arranged horn charts (the riff on “Hell Of A Hat” is that forever kind of cool). Jet-fueled punk tunes like “Dollar And A Dream” and “365 Days” contrast nicely with the poppy nostalgia of “Pictures to Prove It.” And the working-stiff lament “Jump Through the Hoops” closes everything with an effective mix of the boisterous and the forlorn. Put it all together, and you’ve got a record with wider shades of grey than any ska-punk band had a right to explore.

 

85. Eminem – The Slim Shady LP (1999)

Remember when Eminem was funny? Before he was equal parts hero and pariah? Before he cared about haters and leaned on melodramatic drug metaphors? It’s understandable if you don’t, because the polarizing MC only had one album under his belt before he became a passionately beloved and despised superstar. The Slim Shady LP will always be his best musical accomplishment, because it couldn’t possibly be tainted by the rapper feeling like he had to respond or live up to anything. He could be a scrawny no-name white dude hilariously berating Dr. Dre for condoning non-violence, the moment that, for me, best encapsulates the joy of Eminem’s debut. The song, “Guilty Conscience,” was a brilliant concept – have Em play the devil, and Dre play the angel, appearing over the shoulders of a series of protagonists experiencing moral crises. By pitting this mega-talented youngster against his legendary old-guard producer, challenging him to be relevant again, reminding him how much fucking fun music could be, the track bristled with a thrilling kind of energy. Not to say Marshall Mathers couldn’t carry a tune on his own; the rest of the record finds him unfurling verses full of snarky humor and random blasts of open-vein honesty, over dance-floor ready beats that remind us these tracks were not meant to be taken too seriously. The most controversial cut is also one of the best – a blistering spoof of Will Smith’s squeaky clean “Just the Two of Us.” “’97 Bonnie and Clyde” puts the rapper in the shoes of a father driving his baby down to the beach, so he can dump his wife’s body in the ocean. Like a South Park episode that creates an entire plot line just so it can make fun of a celebrity, Eminem crafted this pitch-black satire for the express purpose of dissing Smith’s bland, pandering hit. Future albums would have snatches of this vibrant, rebellious personality, but ultimately fail, because Eminem had become one of those people he so gleefully skewered on The Slim Shady LP – somebody who gives a fuck.

 

84. Urge Overkill – Saturation (1993)

After grunge and alternative rock exploded, A&R execs bent over backwards to sign any band with loud guitars and self-loathing issues. Criticize the approach if you will, but it did result in a major label contract for Urge Overkill, despite the fact that the band wasn’t all that grungey, sounding more like Elvis Costello moonlighting in a cock rock band (not exactly a template to get them on “120 Minutes”). Yes, Saturation, the group’s first effort for Geffen, shares some of the same glam influences as fellow Chicagoans Smashing Pumpkins, and a couple of the riffs possess a slight whiff of Seattle grit. But the pervading mood is Saturday night swagger, not Sunday morning regret. Whether they’re tearing through big, shiny rock anthems like “Sister Havana,” filthing things up with the bloozy riffage of “The Stalker,” or channeling the Ramones on the kinetic “Woman 2 Woman,” Urge Overkill put their desires to be bad-ass above any need to make deep emotional connections (the exception to the rule being the stunning ballad “Dropout”). Add singer Nash Kato’s rich, puckish tenor to the mix, and you’ve got one of the sexiest LPs to ever be pigeonholed as alternative rock. Urge Overkill might’ve worn flannel, but it was most definitely obscured by black leather jackets.

 

83. Outkast – ATLiens (1996)

“Holding on to memories like roller coaster handle bars,” shares Andre 3000 on “E.T.,” one of the many subdued, introspective tracks on ATLiens. It’s an apt sentiment on a record that finds the motormouthed twosome exploring sounds that had little to do with the past, ending up with a record that could arguably be called the birthplace of Dirty South hip hop. Casting themselves as Peach State aliens with checkered pasts, uncertain futures and healthy egos, Andre and Big Boi were fully aware of the bold artistic leaps they were taking on their second album. Leaving the Death Row-Native Tongues hybrid of its debut in the dust, Outkast isn’t afraid to let the music simmer to a slow boil, building “Wheelz Of Steel” on little more than a mournful B3 loop, crafting something truly ominous with the soft vocal hums of “Babylon.” Equally important is the duo’s remarkably constrained vocals; both rappers manage to temper the volume of their rapid-fire verses, without sacrificing any of their intensity. ATLiens suffers a bit from the even more rarified air explored on ensuing Outkast albums, where its formula was expanded to include Parliament-sized funk workouts and world-beating pop singles. These days, it plays like the artful come-down after Stankonia’s life-changing mind fuck. Which is surely cooler than a polar bear’s toenails.

 

82. Emmylou Harris – Wrecking Ball (1995)

He’ll probably be best remembered for the massive hit records he produced in the ’80s, but it’s the deeply resonant career resurrections of the ’90s that impress me most about Daniel Lanois. The producer proved himself to be the polished, perfectionist counterpart to Rick Rubin, exhibiting an uncanny ability to put his own, richly detailed touches on albums by artists with their own fully developed egos (a decade working with Bono will do that). On Emmylou Harris’ 17th album, Lanois pulls off the most sophisticated trick of his career, de-twanging the arrangements for the legendary country songbird, relying on her inimitable voice as the only connective tissue between her previous work and this lushly produced blend of adult contemporary and Americana. It was a calculated risk, one that paid off beautifully. Wrecking Ball is a gorgeous offering of wide-screened, cloudy sky pop, on which Harris proves Lanois right with every syllable she sings. Her crystalline instrument infuses all the regret and hard-earned joy these tracks call for, bringing songs by Neil Young, Steve Earle, Gillian Welch, Jimi Hendrix and Bob Dylan to new levels of delicacy and poignancy, supported all the way by Lanois’ generous washes of reverb. It’s the kind of record that could start a spirited “what is country?” debate – is it the instrumentation and the subject matter, or is it a more intangible vibe? If you’re prepared to argue the latter, make Wrecking Ball your Exhibit A.

 

81. The Black Crowes – Amorica (1994)

For somebody following a band from the very beginning, there’s no better moment than the realization that they’ve elevated their game. To somebody who would have been thoroughly pleased with the same old, same old, even the smallest sign of growth can hit like a firecracker. Yeah, I know I’m talking about The Black Crowes, whose brand of Georgia bellbottom boogie isn’t normally associated with artistic boldness. The band initially caught on as fodder for fans of classic rock dinosaurs in the early-’90s – a time when my love of classic rock dinosaurs was at its peak. I got heavy into the Crowes, loving how Chris Robinson sang to the rafters over all the southern-fried Zeppelin riffs and gospel slow-burns. By the time Amorica came out, the group’s first two albums were classics in my mind. So when I first heard how loose and confident they sounded on the percussion-heavy groove of “Gone,” it was like a Stones fan hearing Beggars Banquet for the first time. That familiar sound had become something richer, earthier, and more significant. Now that it’s been almost 20 years since Amorica gave me that feeling, its pleasures have descended from the spiritual plane. But pleasures they remain, from the organic grooves of “High Head Blues” and “Wiser Time” to the regret-laden epic “Cursed Diamond” and the gorgeous, stoner/Bruce Hornsby ballad “Descending,” whose piano outro still chokes me up.

 

80. Propellerheads – Decksanddrumsandrockandroll (1998)

Whether they’re the result of the legitimate, organic rise of a new artistic sensibility, or something manufactured by critics who are magnanimous with their “next big thing” proclamations, all pop music trends are fads, destined to flame out. So instead of letting them dictate the way you walk, talk and dress, why not do something that will never go out of style – find a good groove and dance to it. This is the message of Propellerheads’ single “History Repeating,” a propulsive spy movie rave up, complete with a gutsy Shirley Bassey vocal, that realized the mainstream potential of electronica while mocking the hype machine that had been predicting just that for years. On the British duo’s first and only LP, they give several examples of the kind of tracks that could inspire critics to go all Nostradamus, doing monstrous things with drums and bass lines that could seemingly stretch on forever without losing their adrenaline-spiking energy. “Take California,” “Bang On!” or the Matrix-approved “Spybreak!” make driving to work feel like a million-dollar chase sequence. When sequenced with quieter, quirkier moments like the groovy kitsch of “Velvet Pants” and the loping, skater hip hop of “360 (Oh Yeah?)” (which features De La Soul at their effortless-sounding best), Decksanddrumsandrockandroll becomes an evergreen listen, an album that will always be as much fun as it was the day it came out. My flannel is long gone, and these beats are forever.

 

79. RZA – Bobby Digital In Stereo (1998)

By the time RZA got around to releasing an album under his own name, he was seen as a pretty solid hip hop double threat – a genius producer who had garnered respect as a rapper as well. Bobby Digital In Stereo solidified this status. Not only was it the treasure trove of dramatic, confrontational beats we’d come to expect (and this a year after the double-LP Wu-Tang Forever. Damn, were we spoiled), it was the first real revelation of RZA’s abilities on the mic. He dishes out some wild, brilliant tongue-lashings here, making the record’s kinda lame “digital v. analog” concept sound like the toughest street battle this side of Mobb Deep, and shouldering the burden of keeping the adrenaline flowing over the course of 17 tracks. That said, Bobby Digital drags just a bit in the middle, but it’s thanks to a glut of guest rappers (RZA only contributes six verses from tracks 8-15). And it pretty much doesn’t matter, because the man closes things in unforgettably explosive fashion. “My Lovin’ Is Digi” is grand and ridiculous and sublime; pairing a huge string loop with a chorus that’s sung with hilarious gravity: “Sometimes, I find someone fuckin’ with my pussy.” Then there’s “Domestic Violence.” Jesus Christ, “Domestic Violence.” An ugly, misanthropic argument between RZA and guest Jamie Sommers, the track is both a raw nerve of rage and bitterness, and a massively successful piece of entertainment. Hearing Sommers laundry list all the things about RZA that “ain’t shit,” how could you not join in?

 

78. Leaders of the New School – A Future Without A Past … (1991)

The title of Leaders of the New School’s debut album is a reference to youth, and all the hope and possibilities it implies. And it completely delivers on that idea. Charlie Brown, Busta Rhymes, Dinco D and DJ Cut Monitor Milo inject every track with endearing, juvenile energy – these guys weren’t just skilled MCs, they were kids whose dreams were coming true, and their joy informed everything they laid to tape during these sessions. This is what makes A Future Without A Past one of the upper-echelon Native Tongues albums; where A Tribe Called Quest and De La Soul were exploring the power of positive thinking, Leaders of the New School was about innocence. A loose schoolyard concept informs classic tracks like “Case of the P.T.A.,” where the guys reflect on how parents and teachers just don’t get it over a completely infectious New Jack Swing groove, and “Show Me A Hero,” a “Gambler”-lifting warning shot to bullies in which Busta steals the show just by reciting his height and weight. If the rising star’s commanding baritone tends to shine just a little brighter than his bandmates, it was all part of LOTNS’ perfect pH balance, leveling out the bizarre shrieks of Brown and the steadying force of Dinko. Hearing them gleefully playing off each other really shines a light on how much the group dynamic has faded from modern hip hop. If you ever get tired of hearing solo records littered with guest spots, crank this up loud, and rejoice in the blissful synergy. Who cares if it gets you detention?

 

77. Lou Reed – Magic & Loss (1992)

Lulu, Lou Reed’s 2011 collaboration with Metallica, quickly and unfairly became shorthand for an artistic train wreck. I’m happy it exists, as proof of how little Reed cared about optics. You could always count on his art being unfiltered. And maybe never more so than his 1992 effort Magic & Loss. Shaken by the death of a friend from cancer, Reed sat down and wrote lyrics that are as subtle as chemotherapy. He marvels at the fact that the same thing that killed people at Chernobyl was helping his friend buy time. He wrestles with ideas of spirituality, bowing to their sanctity one moment, deriding them as “mystic shit” the next. And through it all, no matter how crushingly depressing the songs become, Reed handles them with that classic sense of cool, his resigned sing/speak translating it all into something like hope. He’s always been great at tackling material rich in conflicting moods – “Perfect Day” kicks your ass every time, because it’s about happiness in the context of sadness. Magic & Loss is “Perfect Day” on steroids, then, an album that finds beauty and mystery in the brutal unfairness of life. “I’m sick of looking at me/I hate this painful body,” he sings over the lone, mournful guitar figure on “Magician,” a harrowing tale of a spirit longing for freedom that’s among his best work. Like the album it anchors, it’s riddled with loss, yet feels like magic.

 

76. Depeche Mode – Violator (1990)

When you’re alone, you can rule your own universe. It’s a theme that’s been used for several classic pop songs about adolescence. But when I first saw the video for Depeche Mode’s “Enjoy the Silence,” I’d never heard “In My Room” or “I Am A Rock.” I was in 7th grade, an introverted kid who typically loved extroverted music – bands like Led Zeppelin, AC/DC and Guns n’ Roses  possessed such audacious confidence, it seemed like an interplanetary transmission to a boy like me. But the “Enjoy the Silence” video spoke to me on a deeper level, and could very possibly have been the first work of art to do so. It told me that I wasn’t the only one who shied away from social situations, that, in fact, it was a kingly pursuit to avoid the everyday noises of life. “Words are very unnecessary/They can only do harm,” sings David Gahan as he walks through one gorgeous landscape after another, dressed in a crown and cape and carrying a lawn chair, stopping from time to time to heed the direction of the song’s title. Violator is full of introspective struggles like this – my 12-year-old brain wasn’t savvy enough to understand these songs that wrestled with ideas of faith, and truth, and love. But those haunting goth-pop melodies were more than enough to make me obsessed; plus, as a Catholic school kid I could sense the delicious sacrilege that was being committed on “Personal Jesus.” I loved this album then, despite it standing out of my cassette collection like a sore thumb, and it has only become more poignant with age. The more I’ve discovered about why I love Violator, the more I’ve learned about the younger me, that awkward king of his own quiet world.

 

75. Prince Paul – A Prince Among Thieves (1999)

Given the gritty truths and intense melodramas that have been such a huge part of hip-hop – especially its 1990s golden age – it’s surprising that the genre has given us no stone-cold brilliant concept albums. Is what you’d say if Prince Paul had never made this, easily the greatest hip-hop concept album of all time, and one that I’d take over Tommy any day of the week. A Prince Among Thieves is the story of Tariq, an aspiring rapper and fast food worker who dreams of using his art to get rich and provide for his mother. When he lands a cherry meeting with Wu-Tang Clan, Tariq needs to raise some money to pay for studio time – his demo is a little rough – so he dips his toes into the drug game to make ends meet. While it’s predictable that this story would end tragically, Prince Paul infuses it with flash-forwards, Shakespearean betrayals and bursts of dark comedy, telling a tale that never gets confusing, and always keeps you on your toes. Paul’s production work is on the level with his classic De La Soul material – “Steady Slobbin'” and “What You Got” feature some of the most irresistible soul loops he’s ever dug up. The actors are totally convincing, and guest stars like Kool Keith, Chris Rock, Everlast and Big Daddy Kane make for a hell of a cast. Nobody shines brighter than the star though – Breeze Brewin’ is the main reason we sympathize so much with Tariq; he’s the perfect, unassuming hero in the skits, and his steady, tight flow is the backbone of the majority of the songs.

 

74. Roger Waters – Amused To Death (1992)

After releasing the final Pink Floyd album in 1983 – the underrated anti-war elegy The Final Cut – Roger Waters got into a weirdly allegorical groove, from his pervy-road-trip-as-metaphor-for-something-I-don’t-really-understand solo debut The Pros And Cons Of Hitchhiking to the guy-in-a-wheelchair-ends-capitalism follow-up, Radio K.A.O.S. Not to disparage those albums, both of which have aged far better than anything the David Gilmour-led edition of Floyd ever recorded, but everything about Amused To Death feels like Waters getting back to business, saying to hell with prog-rock librettos and writing the kind of acidic sociopolitical material that made The Wall and The Final Cut so unforgettable. “And the Germans killed Jews and the Jews killed the Arabs and the Arabs killed the hostages and that is the news,” his wonderful backup singer P.P. Arnold belts on “Perfect Sense, Part I,” and that’s the basic theme of the record – organized religion, governments and the media colluding to support humanity’s vilest sins. Because this is a solo Waters album, things do get too preachy for comfort from time to time (especially an uber-cheesy battleground play-by-play from Marv Albert). But you’ve gotta forgive him for these moments, because his rage is so pure, his hook-free arrangements so beautifully meditative, his vision so artful. He spends much of Amused to Death musing about what God wants (spoiler alert: it’s all bad stuff). Say what you want about the man upstairs, but he gave us Roger Waters, and that’s a check in the “pros” column for sure.

 

73. Helmet – Meantime (1992)

From the moment I first heard “Unsung,” which I’m guessing I saw on Headbanger’s Ball, Helmet’s major label debut became an album to save up my allowance and buy (quick side note – nothing will ever sound sweeter to me than the CDs I had to save for a month to be able to afford. Great music will always give me chills, but never again will I feel the blissful release of a record that lives up to my own, self-inflicted hype machine). And while the balance of Meantime didn’t possess anything quite as brutal as that amazingly simple riff, it was perfect for the kind of teen looking to project his weirdo angst on something harder and snarlier than Nirvana. Mixing the mammoth riffage and clipped shouts of Page Hamilton with drummer John Stanier’s deep-in-the-pocket breaks, Meantime was loud, nasty, groove-based hardcore, a sound that hurts just as good 20 years later. Sure, there’s plenty of pain-obsessed Trapper Keeper poetry – Hamilton’s jealous cheerleader screams of “You’re better … die!” being the lowest point. But the guitars are so punishing, and the rhythms so gut-punching, they would smother any attempt at refined lyricism like the runt of a litter.=

72. Sleater-Kinney – Dig Me Out (1997)

“Words and guitar/I got it!” What better way to sum up the joyful noise of Dig Me Out than this chorus to one of its many unshakeable standout tracks? Sleater-Kinney’s third album, and first for Kill Rock Stars, provides equal helpings of molten punk shredding and bouncy British invasion melodies – it’s not a coincidence that its cover is an homage to The Kink Kontroversy. The record sounds for all the world like a trio of gals who love nothing more than plugging in and screaming their guts out. (Which reminds me, Screaming Females’ Ugly, one of my front-runners for the best album of 2012, would in no way exist if not for Dig Me Out.) This palpable exuberance is what makes Dig Me Out something special; instead of wallowing into lines like “I wear your rings and sores/In me, it shows,” singer Corin Tucker sets fire to them, her wild, quavering pipes proving that the death of grunge didn’t stop the Seattle scene from spitting out some startlingly talented, unpredictable voices. Of course, you can’t get by purely on energy. Dig Me Out is riddled with killer pop melodies, Carrie Brownstein’s shit-hot guitar playing, and deftly layered sequences that belie the whole garage band aesthetic – take “Words and Guitar,” where Tucker’s vocal devolves into a primal scream and Brownstein chimes in with a cheery backup vocal (“Can’t take this away from me/Music is the air I breathe”), all over a sun-kissed riff straight out of a Searchers song. Sleater-Kinney makes it all sound exhilaratingly simple, as sure a sign as any that we’re hearing a great band at its peak.

71. Pearl Jam – Ten (1991)

When I was 14, I considered Ten to be one of the Great Rock Albums, on a level with Led Zeppelin II or Back In Black. But if you’ve read my introduction to this list, you’ll understand why I was nervous to listen to Pearl Jam’s monster debut front to back, for the first time in at least a decade – what Ten has inspired in its wake has been pretty horrifying. And I’d be lying if I said I didn’t cringe during “Once,” the album’s propulsive opening track. I can appreciate melodrama, but as Eddie Vedder growled “Once upon a time/I could love myself,” I realized how rough around the edges this gifted vocalist was in 1991. Vedder connected with listeners from the get because he sang with naked emotion, but on Ten, he often gets lost in these waves of feeling, his grunts and wails coming off almost comical. At the end of “Once,” Vedder lets loose his most heinous guttural burst (“YUH-HEA-HEA-YUH-HEA-HEA!!!!”), which I will now claim as the #1 reason Chad Kroeger, Scott Stapp and Chris Daughtry sound like they do. That’s all to explain why Ten is #71 on this list, instead of in the top 20. It remains a smorgasbord of killer guitar riffs, and is full of songs that shamelessly aim for arena nosebleeds, with none of the artsy experiments and ham-fisted politics that would make vs. and Vitalogy so uneven. And when Vedder calms down, his vocals are gorgeous – the ballads “Oceans” and “Release” are two of the album’s strongest cuts as a result. Then there’s “Alive,” perhaps the perfect example of how Pearl Jam combined the angst-ridden energy of grunge with the comfortable, crowd-pleasing tropes of classic rock – if you thought existentialist crises and guitar solos couldn’t mix, here’s your proof.

45. Snoop Doggy Dogg – Doggystyle (1993)

The first rapper we hear on this, the definitive statement from the California G-funk era, isn’t Snoop Doggy Dogg. Or Dr. Dre. It’s the forever slept-on Death Row mercenary The Lady of Rage, whose joyful, electrifying verse sets the tone for record to come – “Kickin’ up dirt and I don’t give a god damn,” she spits. It’s an immediate sign that Doggystyle is going to be more fun than Dre’s iconic 1992 opus The Chronic. While that record was concerned with settling scores and establishing myths, Snoop’s is concerned with partying and making dick jokes. His laconic flow and youthful effervescence is the ultimate counterpoint to Dre’s bloodshot Funkadelic grooves. The opening salvo of “G Funk,” “Gin & Juice” and “Tha Shiznit” is a cresting wave of positive vibes that still makes me feel like I’m blissfully plastered, with the warm sun on my face. This is the record that should’ve been named after weed.

 

44. Pearl Jam – No Code (1996)

Even when Pearl Jam was conquering the world with sweeping arena rock anthems, they actively rejected the “arena rock band” label. They stopped making videos, fought Ticketmaster, defaced #1 albums with drunken accordions and bizarre sound collages. But it wasn’t until No Code that they actually stopped sounding like rock stars. It remains the band’s most patient and honest effort, with themes of spirituality taken to heart. What hits you at first is the eclecticism – Eastern melodies and spoken word and muddy punk all rubbing shoulders. But what’s endured are the ballads, some of the loveliest in ’90s rock. There’s no attempt to mask the weariness in Eddie Vedder’s vocals or Brendan O’Brien’s loose, shaggy production. Whether it’s the somber self-criticism of “Off He Goes” or the gentle country lullaby “Around the Bend,” we’re hearing musicians so exhausted by stardom, all they had left to do was be themselves.

 

43. Public Enemy – Fear of a Black Planet (1990)

I can think of no better example of sampling as an art form than Public Enemy’s third album. Of all the classics made during rap’s Wild West sampling era – before attorneys got wise to the fact that producers in this new genre were chopping up copyrighted material – Fear of a Black Planet has the most consistent, fully realized vision. PE’s production crew The Bomb Squad deploys 129 samples over the course of 20 tracks, leaning heavily on James Brown and Sly Stone breaks but also mining Prince, Uriah Heep, Sgt. Pepper’s, Hall & Oates, and Vincent Price’s laughter from “Thriller.” Amazingly, the album doesn’t sound like a collage or mash-up, because The Bomb Squad treats these samples like building blocks, just 129 of the instruments used to flesh out PE’s relentless, confrontational funk. This isn’t a wall of sound. It’s a skyscraper. And when the man rapping over it is Chuck D in his prime, his voice booming like timpani, full of righteous outrage and Afrocentric pride? You can’t imagine anything ever sounding bigger.

 

42. Nick Cave and The Bad Seeds – Let Love In (1994)

When an artist begins and ends an album with songs called “Do You Love Me?” it’s fair to wonder if he’s a bit starved for attention. When Nick Cave did this, on his eighth Bad Seeds album, he was 36 years old, prime crisis territory for a rock star. It could just be dark fiction from a master storyteller, but either way, Let Love In is a towering work about sin, regret and death – a Leonard Cohen album adapted into a horror movie. Cave litters his lyric sheets with defeated characters, wasting away in bars and planning their funerals. Sacred thresholds are violated left and right, by lingering devils, or lying politicians, or lovers who have to be let in like vampires. I find it telling that Cave gets nostalgic on a pair of twitchy punk tunes that sound like old Birthday Party B-sides. Over the churning, serrated guitars of “Thirsty Dog,” he apologizes like he’s got nothing to lose: “You keep nailing me back into my box / I’m sorry I keep popping back up.” It certainly sounds like he was worried his career was toast. And rather than denying these feelings of fear and vanity, he faced them head-on in his songwriting. Something that I, for one, will always love him for.

 

41. A Tribe Called Quest – Beats, Rhymes and Life (1996) 

When a genre is as young as rap was in the ’90s, its elder statesmen are too. Q-Tip and Phife Dawg were only 26 and 25 when their fourth album dropped, but they were already done as influencers of the genre. By ’96, their jubilant, jazz-inflected Native Tongues movement was no longer a thing, with groups like Outkast, The Roots and The Fugees using it as a launchpad for their own signature sounds. Beats, Rhymes and Life succeeds by readily embracing all of this. Undeviating in its polished, radio-friendly approach, the record documents Tribe entering its accelerated golden years with ease. Never have they sounded slicker. And that’s not a complaint. Those trademark Fender Rhodes loops are even simpler and spacier. And the drum programming is just gorgeous. To this day I’ve never heard snares crack with such reassuring warmth, like pebbles hitting your bedroom window. As always, Tip and Phife float effortlessly through it all, resulting in some of the catchiest rap of the decade – especially “Motivators,” where Phife encapsulates the vibe with his typical conversational flair, “This here groove was made for vintage freestylin’ / Feelin’ like I’m chillin’ on a Caribbean island.” Moments like these make questions of age and relevancy feel silly, boiling hip hop down to a simple credo: When the beats are good, and the rhymes are good, life is good.

 

40. Nirvana – Nevermind (1991)

Nirvana’s second album probably has more baggage than anything on this list. It’s been credited with loosening the Baby Boomers’ stronghold on pop culture, and inspiring the thrift-store fashion and blasé attitude of a new generation. It’s remarkable how little this mountain of hyperbole affects the experience of listening to it today. Sure, Nevermind no longer feels revolutionary – as one of the last world-dominating albums of heavy guitar music, it has more in common with Metallica’s Black Album then originally thought. But it’s as much of a blast as ever, the riffs and melodies gelling in ways that still feel exciting. A major key to this longevity: Kurt Cobain had no shame about letting his influences show, whether they were hip in ’91 or not. So while these songs buzz with the artful noise of The Pixies, they’re also girdered by the pop constructs of The Beatles. And “Smells Like Teen Spirit,” that legacy-defining hit, lifts heavily from a Boston song. As a result, whether we’re hearing the irresistible “yeah yeah” chorus of “Lithium” or the primal screams of “Territorial Pissings,” our urge isn’t to break any rules. It’s to sing along.

39. Me’Shell Ndegéocello – Peace Beyond Passion (1996)

Like most people, the first time I heard Me’Shell Ndegéocello was when she duetted with/propped up John Mellencamp on a smash-hit cover of Van Morrison’s “Wild Night.” Her fluid bass playing breathed new life into one of Morrison’s catchiest riffs, turning a stale idea into one of the funkier things we heard at the supermarket in 1994. Two years later, Ndegéocello’s second solo effort delivered on that song’s promise and then some. Peace Beyond Passion is full of rich, meditative R&B grooves that have only a passing interest in chart success. While her band is full of ringers – Billy Preston on organ, Joshua Redman on sax, Bennie Maupin on bass clarinet – her talents shine brightest. Her bass playing is incredibly expressive. Her singing voice is a deep, reassuring rasp. And her songwriting is bold. I love thinking about all the Mellencamp fans that must’ve checked out the first single – a heartbreaking, six-minute takedown of homophobia called “Leviticus: F****t” that boasts an irresistible three-note groove. It’s an eye-opening lesson about what funk can do. Ndegéocello is totally fine with you dancing to it. Just remember that she’s invited all of humanity to the party.

 

38. GZA – Liquid Swords (1995)

The sleeve of this record says “GZA,” but it’s hard to think of it that way. Because while Liquid Swords is indeed a showcase for Wu-Tang Clan’s most cerebral, cold-blooded storyteller, it’s even more so for its producer. RZA’s run from ’93 to ’97 was jaw-dropping in both its quality and quantity. It should be spoken of in the same hushed, reverential tone as Brian Wilson’s mid-’60s streak. And Swords is the purest expression of his vision. Dramatic samurai flick dialogue sets the tone for beats that pulse with the dark exhilaration of vengeance fulfilled. On “Duel of the Iron Mic,” chopped pianos and mechanical thunderstorms underscore GZA’s tale of “bloodbaths and elevator shafts.” “Cold World” dresses the melody from Stevie Wonder’s “Rocket Love” in icy, dissonant strings. “4th Chamber” pairs a floating sitar loop with beds of frayed, crunching power chords. These are themes for flawed heroes, navigating a world where violence is unavoidable. “I got your back / But you best go watch your front,” goes the chorus to this album’s first single. On it, RZA fills our speakers with trumpets, as sad and proud as a military funeral.

 

37. Slayer – Decade of Aggression (1991)

It’s hard to capture the feel of any live show on tape – to transport listeners to that venue, in that moment, without sacrificing the clarity of the performance. But to nail what it felt like to see thrash titans Slayer in 1990? That’s pretty much a goddamn miracle. And it’s what producer Rick Rubin pulled off with this 10th anniversary double-disc set. Not only does Decade of Aggression give us a fantastic mix of the band’s punishing, quicksilver onslaught – so crisp you can hear every syllable hurtling from Tom Araya’s throat – but it gives us just enough of the ambience of venues like the Lakeland Coliseum, smack dab in the center of death metal’s Florida heartland. Rubin lets a full 40 seconds of crowd noise go by until the extended intro of “Hell Awaits” kicks in. A chorus of demons start hissing in a backwards language. Their numbers grow. The volume rises. The anticipation is palpable. Then Jeff Hanneman lays into the hyperactive Sabbath riff, and you can smell the sweat flying from 10,000 dirtbags, headbanging with abandon. No matter where this comes on, in my car or my cubicle, I make it 10,001.

 

36. Mobb Deep – The Infamous (1995)

The concept of “keeping it real” is about as relevant as raising the roof these days. But Mobb Deep’s second album will always stand as a reminder of just how grim things can get when you take this credo seriously. Emcees Prodigy and Havoc weren’t interested in glorifying the challenges of their day-to-day lives in the Queensbridge projects. So they painted pictures of anxiety and pain, fierce loyalty and sudden loss. Walks home alone at night are pregnant with terror. Decisions aren’t made until potential prison bids are weighed. Yet, completely due to the power of their flow and production that bends piano keys like Twizzlers, The Infamous had hits. There will probably never be another song like “Shook Ones Pt II,” which brought the dark night of the soul to the dance floor. “Ain’t no such things as halfway crooks,” the chorus proclaims over a bewitching, slithering beat. It’s about how the streets leave no room for pretenders. If you’re still sensitive enough to be shaken by life, you don’t know how lucky you are.

 

35. Beck – Odelay (1996)

After scoring an accidental smash hit with the slacker-M.C. cut “Loser,” Beck struggled with what to do next. He recorded an entire album of dour lo-fi folk and then scrapped it, eventually opting for the other extreme – a technicolor patchwork collage of golden age hip hop and singalong country that’s almost passive-aggressively catchy. He brought in The Dust Brothers (who weaponized ’70s radio hits so deftly for the Beastie Boys), to give a kitschy, sample-heavy sheen to his roots rock compositions. He wrote cryptic magnet-poetry lyrics that sounded good, but meant nothing, making an enduring meta statement about the inherent emptiness of pop hits. He used his disdain for the mainstream to create the most universally beloved album of his career. It’s as ironic as it is iconic. Does it get more ’90s than that?

 

34. Bikini Kill – The CD Version of the First Two Records (1994)

When we press play on an old recording, chances are we’re going to feel some kind of distance from it. This is not the case on the first two EPs from riot grrrl pioneers Bikini Kill, re-released on one CD back in ’94. Kathleen Hanna leads the quartet through one 4-track punk thrasher after another, driven by the kind of unquantifiable energy that’ll have you driving 10 mph faster without realizing it. And her lyrics remain as exhilaratingly confrontational as her screams. “Does it scare you, boy, that we don’t need you?” she snarls. It’s amazing (and depressing) how relevant these songs remain. The patriarchy is still hurting us all, but the hairline fractures are getting easier to see. The louder we play this, and the more seriously we take its outrage, the faster we can watch them grow.

 

33. Prince – The Black Album (1994)

If there’s one thing that’s guaranteed to sound forced, it’s a rock star’s late-career attempt at shoring up their street cred. Unless you’re Prince, that is. In 1987, Prince made The Black Album to appease critics who accused him of selling out. It was the filthiest funk music he’d ever laid to tape, P-Funk and Sly-indebted vamps shot through with odd lyrical obsessions, with little regard for running times. He makes fun of rappers for not singing, steps into the mind of a celebrity stalker, and pitch-bends his voice to become the gun-waving chauvinist villain “Bob George.” Famously, the artist changed his mind about releasing The Black Album at the last second, convinced of its “evil” after a visit from god (or his ecstasy dealer). It sat on the shelf until 1994, when we all got to hear how wrong he was. Prince, playing funk guitar like he’s got something to prove? There is no clearer force for good.

 

32. Handsome Boy Modeling School – So, How’s Your Girl? (1999)

It’s gotta be hard enough for a band with multiple songwriters to deliver a clear, consistent aesthetic. But a group with two lead producers? It would seem almost impossible, given the complete control the best producers usually demand. Yet in 1999, the renowned hip hop knob-twisters Prince Paul and Dan the Automator joined forces to make an undisputed classic. So, How’s Your Girl? is many things – a silly concept album based on a Get a Life episode; a how-to manual for deploying guest artists; a summit meeting of peak ’90s rap and electronica. But most strikingly, it’s a pure distillation of the playfully deployed golden-age samples of Paul and the dramatic sci-fi soundscapes of Dan. Handsome Boy Modeling School eventually fizzled out due to artistic differences. But we’ll always have this album, and its grand, magnetized agreements.

 

31. Old 97’s – Fight Songs (1999)

The summer Fight Songs came out I worked at a nursery, loading cedar chips into trunks and getting odd rashes from trees. And if my boss overheard what I was singing to myself as I worked, she would’ve had to consider an intervention. “Lonely / Baby I’m not lonely / I’ve got my imaginary friends” went this record’s most inescapable chorus, the high harmonies lingering over bright, strummy production. I could’ve used better friends back then, it’s true. But this was a case of whistling while you work – Fight Songs remains one of the catchiest damn things I’ve ever heard. Few artists have been able to take typical country-western themes of despair and simultaneously heal them through melody like this. Rhett Miller didn’t add an ounce of grit to his vocals, lending sincerity to sad-sack anthems like “Busted Afternoon,” “Jagged” and the aforementioned “Lonely Holiday.” The walls might’ve been closing in, but the ceiling was opening up.

 

30. Radiohead – The Bends (1995)

In 1993, at the height of grunge’s marketability, Radiohead released “Creep,” a single that nailed the genre’s central oxymoron – self-loathing art that draws a crowd. Suddenly, these guys were getting what seemed like their 15 seconds. Except they didn’t relish their dalliance with stardom. It made them feel alienated and exhausted, to the point where they started to seriously ponder the fleeting nature of life itself. And then they made an album about that. “You can crush it, but it’s always here,” warns Thom Yorke on the opening track of The Bends, as if the reassuring swirl of Wurlitzer and guitar was the only thing keeping the reaper off his back. Guitarist Jonny Greenwood utilizes way more than his volume knob this time around, creating atmospheres of aching wonder and wanton destruction. From the consumer culture nightmares of “Fake Plastic Trees” to the raw existentialist dread of “Street Spirit,” Radiohead confront one unfixable, harrowing reality after another, while writing choruses that blot out the world. Instead of eating hot dogs like most of us do when we feel like nothing matters, they made an attempt at shared catharsis. Self-loathing had made way for selflessness.

 

29. Portishead – Dummy (1994)

Seattle wasn’t the only rain-spattered town to become famous for its gloomy music scene in the ’90s. Bristol, UK, was ground zero for “trip hop” – a fusion of rap, electronica and post-punk that played like the soundtrack to a Bond movie where his greatest nemesis is loneliness. In 1994, the genre landed its own Nevermind, in the form of Portishead’s bewitching debut. Dummy was a trip-hop blueprint, with an emphasis on the blue – singer Beth Gibbons confronts the day-to-day realities of depression in an absolutely haunting voice. The music fits her like a shroud. Theremins cry over echoing minor chords. Single words become garbled and transformed by bandleader Geoff Barrow’s emotive scratching. “In this moment/How can it feel this wrong?” Gibbons asks, like a forgotten spirit trying make herself heard. In that moment, you know why people decide to investigate that mysterious sound in the attic. Some part of us wants to be haunted.

 

28. The Beta Band – The Three E.P’s (1998)

In 1994, an album called Chant hit #3 on the Billboard charts. It featured old recordings of Spanish monks doing what the title promised, and was marketed as a surefire stress reliever. It sold two million copies. My dad had one of them. I have no idea if the Scottish “folktronica” outfit The Beta Band were Chant fans, but their music strives for a similar kind of transcendency – not exactly the status quo in indie rock back then. Over the course of three EPs, the band explored the limits of patient, circular songwriting, finding a throughline from “Alice’s Restaurant” to ambient techno – a mix of acoustic guitar strumming and entrancing electronic noise that feels like it could go on forever without losing steam. (The only artists less concerned with radio play? Those monks.) All three of these extended players were collected on this single disc, and while it did land them a minor hit with the slow-build stoner ballad “Dry the Rain,” these guys were after something deeper than mere hooks. The Beta Band didn’t just catch your ear. It absorbed you, tip to tail.

 

27. Mos Def – Black On Both Sides (1999)

I’m a sucker for artist autobiographies. There’s always the chance those pages contain a deeper understanding of a performer’s state of mind during the creative process – ideally resulting in an even closer relationship with their art. Rap is the only genre that regularly weaves these meta commentaries within the music itself; emcees often explain what drives them to write rhymes, how the process makes them feel, and why they’re so much better at it than you. And I can’t think of any rapper who has written about writing better than Mos Def on his solo debut. “My restlessness is my nemesis / It’s hard to really chill and sit still, committed to page / I write a rhyme, sometimes won’t finish for days / Scrutinize my literature from the large to the miniature,” he raps. He devotes a whole chorus to Rakim’s classic bars about being trapped between the lines. He wrestles with his responsibilities as an artist but decides to soldier on and follow his Umi’s advice: “Shine a light on the world.” Black On Both Sides does just that, with golden-hour production that makes samples sound like backing bands, leaping from R&B to jazz to hardcore without ever losing that comforting sheen. Fluid, openhearted, and buried deep in the pocket, it’s got all I ever need to know.

 

26. Mariah Carey – Mariah Carey (1990)

It started with one note. A strange, reverberating synthesizer, drawing us in like a UFO tractor beam. Then the chimes tinkle, the vocals do a melismatic dance, and we’re there, swaying to the timeless doo-wop melody of Mariah Carey’s first single, “Vision of Love.” To an aspiring R&B singer at the time, that note must have felt like the X marking the spot of their way forward, their opening chord of “A Hard Day’s Night.” The song, and the self-titled album it anchored, introduced Carey as a writer and singer with an innate ability to craft worldbeating hits from R&B and gospel ingredients. Her fingerprints have been all over pop music ever since – Beyoncé has credited “Vision of Love” with inspiring her to do vocal runs. That powerhouse of a voice naturally gets all the attention, elevating this record’s twinkling Whitney arrangements into something more profoundly human. But Mariah Carey remains a spine-tingling listen because of the crispness and unexpectedness of the writing – like “Someday,” with its finger-wagging prognostications of regret. Or “It’s All In Your Mind,” which rubs Tiger Balm onto a partner’s trust issues. Or the closer, “Love Takes Time,” which features a narrator that didn’t follow the lesson of the song title, staring in the mirror, trying to forgive themselves. Three of the four songs I’ve mentioned here were #1 hits. This was pop music that gave you so much more, right from note one.

 

25. Wilco – Being There (1996)

In 1996, things weren’t exactly going Jeff Tweedy’s way. It’d been a few years since the nasty breakup of alt-country pioneers Uncle Tupelo, and Tweedy’s new band wasn’t doing as well as his old partner Jay Farrar’s. So he literally doubled down, recording a double album and refusing to budge when his label balked. He called it Being There, after the 1979 Peter Sellers movie about a clueless man named Chance who floats to the top of society. “Misunderstood,” the album’s first song, starts as a ballad about not belonging, and ends with a thunderous punk catharsis: “I wanna thank you all for nothing!” It’s Tweedy trying the Chance method of getting famous, sharing what’s on his mind and letting the chips fall where they may. It’s selfish, and dynamic. But thankfully, Being There isn’t all vitriol. The brilliant multi-instrumentalist Jay Bennett joined Wilco for these sessions, burnishing every track in some way, be it a ringing pedal steel note or a heartfelt backing vocal. And Tweedy full-on embraces his love of classic rock, from the shameless Stones rip-off “Monday” to the T. Rex boogie of “I Got You.” He may have missed the point of that movie – Chance is a stand-in for every idiot who’s coasted to the White House on white male privilege – but he made himself a masterpiece all the same.

 

24. The Pharcyde – Bizarre Ride II The Pharcyde (1992)

There’s something inherently rewarding about talented people not taking themselves seriously. Like Meryl Streep playing an ego-drunk Danielle Steele villain in She-Devil. Or Werner Herzog narrating an episode of Parks & Recreation. Or a quartet of accomplished dancers forming a goofy rap group called The Pharcyde. After landing a record deal on the strength of a song full of mom jokes (e.g. “Your mama’s got a peg leg with a kickstand”), Fatlip, Slimkid3, Imani and Bootie Brown poured all their youthful energy and comedic chops into Bizarre Ride II the Pharcyde. Whether they’re rapping about getting high, or arrested, or ignored by a woman, their rapid flows, class-clown antics, and legitimate moments of clarity formed the backbone of a record that was so much more than funny. These guys were smart enough to avoid the kind of wooden sketch comedy that marred many a ’90s rap album – instead, they freestyled about hypothetical presidential power over a vamping live band. Oh, and did I mention Bizarre Ride is a clinic in sample-based beatmaking? J-Swift’s celebratory, jazz-inflected production has aged wonderfully – it’s entirely possible the inventor of the confetti gun was listening to it when inspiration struck.

 

23. Rheostatics – Introducing Happiness (1994)

Sire Records had no idea what to do with Rheostatics’ fourth album. Even though it featured “Claire,” by far the biggest hit of this Ontario cult quartet’s career, Introducing Happiness was a carnival of clashing ideas – the deep cerulean of a sci-fi ballad, next to a lime green fever dream of a giant hummingbird, blurring into the mercury-silver glow of a jazz ode to the Russian lunar cycle. Factor in singer Martin Tielli’s anti-Vedder quaver and guitarist Dave Bidini’s explosive, angular noodling, and the Buzz Bin probably felt out of reach (although the Flaming Lips, this band’s closest American counterpart, managed to pull it off). Who cares about this 24-year-old industry context, you say? Well, you may have forgotten just how deeply odd, and disarmingly pretty, this album is. You may have forgotten about “Cephallus Worm/Uncle Henry,” which sounds like a room of amateur impressionists covering “Purple Haze” through a fog of nitrous oxide. You may have forgotten about lines like “I’m dripping water on your gills / You’re such a beautiful thing.” These guys had been given a second chance to prove themselves as a commercial force, and this is what they made. God bless them.

 

22. Björk – Debut (1993)

There’s a moment on Björk’s solo debut where we get a chance to step back and truly take stock of what we’re hearing. In the middle of the deliriously catchy raver “There’s More to Life Than This,” the singer pulls us out of the club – a door slams, muffling the music behind it. It’s a disorienting experience; I thought my speakers had shorted out the first time I heard it. But before I could start messing with the wires, Björk was singing again, in full-throated a cappella – “We could nick a boat / And sneak off to this island!” When the beat comes back, it’s a whole new kind of high. This, right here, is what it was like to listen to Björk in the ’90s. Anytime we thought “perfectly enjoyable” was good enough, we felt a pull at our sleeves, away from complacency and toward a previously unimaginable Icelandic adventure. Debut isn’t quite as richly layered as her future triumphs, but the building blocks alone make it a classic – the insanely creative techno production, the vintage movie musical balladry, a voice with a majestic ornithology all its own. There’s more to life than this, but only because Björk’s next album was even better.

 

21. Bob Dylan – Time Out of Mind (1997)

In the summer of 1997, Bob Dylan was hospitalized with a fungal infection that was attacking his heart. He’d already had his 30th album, Time Out of Mind, in the can by then. Its songs weren’t inspired by this particular crisis. But it’s a haunting, melancholy struggle just the same – a man on the verge of becoming a boomer relic, coming to terms with the mortality of his mind and body. Here was rock’s most renowned lyrical obfuscator, writing with eerie clarity about failed marriages, stale hopes, and looming shadows. “I got no place left to turn / I got nothin’ left to burn,” he sings on “Standing in the Doorway.” He’s spent. But ironically, Time Out of Mind was Dylan’s most fulfilling work in decades. With producer Daniel Lanois back in the fold – he produced Dylan’s underrated 1989 album Oh Mercy – these songs of woe get the sonic TLC they deserve. From the ominous, echoing organ of “Love Sick” to the sauntering blues vamp that makes the 16-minute “Highlands” feel like a reasonable length, Lanois’s warmly evocative touches remind us that while the narrators are alone, the musicians are anything but. “It’s not dark yet / but it’s getting there,” Dylan confesses. His talent has rarely shone brighter.

 

20. Beastie Boys – Check Your Head (1992)

That cover image you’re looking at right now, with the Beastie Boys sitting on a curb next to their instrument cases? It wasn’t a joke. Even though Mike D, MCA and Ad-Rock had just reinvented themselves, against all odds, on the triumphant samplepalooza Paul’s Boutique, they took an even bigger risk on the follow-up – ditching their old producers and proven formulas so they could play their own loose concoction of funk, rap and hardcore punk. Like the Monkees, novelty-act status had masked the fact that the Beastie Boys had legitimate musical chops. Check Your Head is stuffed with monumental riffs and meditative instrumentals, lovingly sequenced into 20 tracks that resist the shuffle button. The rapping reflects this anything-goes, jam-session mentality, summed up by Mike D on track one: “All I ever really wanna do is get nice / Get loose and goof a little slice of life.” Only six years after “Brass Monkey” squawked its way onto the charts, this deeply musical, effortlessly electrifying LP entered the world. It was irrefutable proof of one of popular music’s greatest evolutions.

 

19. Nas – Illmatic (1994)

There’s a moment, before Nasir Jones raps a word of his debut album, that underlines how incredibly fresh his artistry was. As the ominous, subway-rattling bass line of “NY State of Mind” ramps up underneath, the 20-year-old MC confesses into the mic, “I don’t know how to start this.” And then, even though the ink is still drying, he jumps in, telling stories about life in New York’s Queensbridge projects that are so detailed, you can hear the dice hitting the walls: “On the corner bettin’ Grants with the cee-lo champs / Laughin’ at base-heads tryin to sell some broken amps.” Illmatic is a masterpiece of scene-setting, a clinic of internal rhymes, and an emotional watershed from a composition-book-scrawling kid who grew up surrounded by violence and nourished by poetry. And the beats – crafted by top producers of the ’90s – dramatically soundtrack these vivid scenes, from the clave-clacking quiet-storm R&B of “Life’s a Bitch” to the mournful organ loop of “Memory Lane.” He may have had no clue how to begin, but once Nas took that leap, it would be 38 minutes before he touched the ground.

 

18. Lucinda Williams – Car Wheels on a Gravel Road (1998)

Lucinda Williams wanted her fourth album to sound a particular way. Warmer, punchier, more like the Pretenders or Steve Earle – “His vocals were more outfront, and it was a bigger sound,” she said about the latter. And thankfully, she stuck to her guns, through six years of label flameouts and disagreements with stubborn male producers (Earle included). Because Car Wheels on a Gravel Road sounds big in the most authentic possible way, a deeply rooted Louisiana oak that we can lean up against for an afternoon. It opens with “Right In Time,” an achingly physical love song that pairs visceral yearning (“Think about you and that long ride / I bite my nails, I get weak inside”) with a chiming guitar riff that’s as fulfilling as the sound of your lover pulling into the driveway. As Williams goes on to explore the nooks and crannies of Southern music, from jukebox country to jailbird folk and dobro-happy roots-rock, the connective tissue is her voice – defiantly front and center, singing about wandering spirits seeking meaning, making it seem like the journey itself could be enough.

 

17. The Roots – Things Fall Apart (1999)

With the millennium coming to an end, the Clinton crime bill wreaking havoc on black communities, and an extended era of anti-Muslim fear-mongering right around the corner, The Roots released an album called Things Fall Apart. It was, quite ironically, the moment where everything came together for them. There’s a feeling of unrest throughout, an understanding that now it’s time to spark shit. Beats fade away in the middle of verses, the rappers left alone to soldier on. Its lead single, a love song about trust, prominently features the line “sometimes relationships get ill.” Its bookends are an argument between musicians from Mo’ Better Blues and a spoken word screed about the cycle of abuse. But even with the pull of these dark undercurrents, Things Fall Apart is a delight to listen to, a telepathic group at its peak, lovingly laid to tape. The crisp crack of Questlove’s snare; Kamal Gray’s nourishing Fender Rhodes vamps; Black Thought’s sweat-on-the-mic intensity – it gels in that next-level Revolver way. Resulting in a record that makes you feel grateful for its artistry, and wary of what’s to come.

 

16. Smog – Knock Knock (1999)

“Let’s go to the country / just you and me,” goes the opening lines of singer/songwriter Bill Callahan’s seventh LP. But that invitation wasn’t as casual as it sounded. Knock Knock found Callahan expanding his palette, both lyrically and instrumentally, the obscure lo-fi vision of his early albums making way for richly rendered, naturalistic tone-poems about empathetic prison guards, bone-chilling childhood traumas, and restorative balms of affection. “I lay back in the tall grass / And let the ants cover me,” he sings in his rumbling basso, describing a moment of psychological healing like Leonard Cohen on a Thoreau kick. The music is equally exploratory, using bouncing cellos and children’s choirs to buoy Callahan’s lush, searching guitar. It’s a formula he’d take to even more panoramic heights later on in his career, a smirking cowboy wading through amber waves of pain, coming out the other side humbled and smitten. Making Knock Knock even more meaningful in context. This isn’t just some invitation to a three-day weekend on the lake. It’s an artist taking the first steps into the underbrush of his soul.

 

15. The Flaming Lips – The Soft Bulletin (1999)

On a trip to Hawaii a few years back, my wife got bit by what we thought was a spider. The bite kept getting worse, so we called poison control. I was scared shitless that I was going to lose my person, while surrounded by the most vibrantly alive environment I’d ever seen. The Flaming Lips must’ve known this feeling. Because their masterpiece, The Soft Bulletin, is full of songs that are acutely aware of life’s impermanence. Yet they’re surrounded by optimistic, awe-inspiring orchestral arrangements that do justice to the laziest Pet Sounds reference. And oh yeah, there’s literally a song called “The Spiderbite Song,” which does not require a personal encounter with potentially deadly insects to appreciate. Producer Dave Fridmann goes borderline Disney with the arrangement, slathering it with trilling harps and tinkling pianos. Yet it’s a delivery system for a raw-as-hell truth – love and devastation are a switch, and it can be flipped by the tiniest twist of fate. “If it destroyed you / It would destroy me,” admits Wayne Coyne on the chorus, balancing the scales without dispelling the magic. My wife’s bite turned out to be from a non-poisonous scorpion, further proof that she’s a total bad-ass. But I’ll always feel a little bit shaken by the memory. Hearing Coyne’s voice, trembling with relief as it floats high above these flourishing soundscapes, it’s impossible to not be moved. Because at any moment, it could’ve fallen.

 

14. Beck – Mutations (1998)

These days it’s common knowledge that Beck Hansen is a singer/songwriter capable of incredible pathos. But the first time I heard Mutations, I had no idea. The crate-digging hipster earthquake of Odelay was still ringing in my ears. So I was floored by this collection of languid folk and country sway-alongs, its rich, organic warmth somehow unscathed by an aggressively bleak lyric sheet (“We ride disowned / Corroded to the bone”). Nigel Godrich, fresh off producing OK Computer, buoys Beck’s tender crooning with reassuring swaths of synths, sitars, and harpsichords. Friendly, almost amateurish harmonica solos add to the humanity. And while there are no donkey samples or rapped non-sequiturs, Beck’s quirks are all over this album, giving it a ramshackle, lived-in feel. “Canceled Check” ends with the band having a collective stroke, randomly bashing on things. The hidden track “Diamond Bollocks” leaps between seething Stooges riffage and gentle birdsong. And his lyrical flights are as strikingly weird as ever: “A desolate wind / Turns shit to gold / And blows my soul crazy.” To encounter all of this unexpectedly was like having a profound conversation with somebody you thought you knew. Realizing there’s way more to them than you thought. And looking forward to hearing from them again.

 

13. De La Soul – Buhloone Mindstate (1993)

Grunge bands got tons of credit for rejecting the spoils of stardom in the 1990s. But none of them explored this conflict on tape quite like De La Soul, who made entire concept albums about what it meant to be a rap star. They called their second LP De La Soul Is Dead, shattering the cuddly, neo-hippie image that made them famous. A few years later, they dropped Buhloone Mindstate, its title borne from a stated desire to “blow up, but not go pop.” It sounds like what it is – a rap group at the peak of its powers, trying its hardest to not make hits. So we get thickets of ’70s soul and ’80s rap samples, live horns, and clips from the movie The Five Heartbeats (all of which appear on the monumental “Patti Dooke”). Maceo Parker gets five minutes to just solo. Same for the Japanese rap trio Scha Dara Parr, who get a stripped down drumbeat to freak out over. And then there’s Posdnous, De La’s de facto leader, who makes sure we’ve got our seatbelt on during all these thrilling left turns. He overstuffs his verses with introspective journeys and biting social commentary, stating his case clearly and prolifically. “I am Posdnous / I be the new generation of slaves / Here to make papes to buy a record exec rakes,” he shares on “I Am I Be,” doing justice to the authenticity of that title. It’s lovely how much De La Soul cared about this stuff. They stayed true to themselves in the spotlight, exposed who was really benefitting from their hard work, and channeled it all into groundbreaking, revivifying music. It’s been 26 years, and it’s still blowing up.

 

12. PJ Harvey – To Bring You My Love (1995)

Countless Westerns end with their male leads going out in a blaze of glory, because they valued their own concept of justice  over anything else. On her third album, PJ Harvey had had enough of that shit. To Bring You My Love is written from the perspective of the women in these stories, those unconsidered widows and jilted lovers whose existential pain is usually seen as acceptable collateral damage. “I love him longer / As each damn day goes / The man is gone / And heaven only knows,” she sings on the album’s final song, establishing the permanence of grief before the music fades. Her narrators plead with everyone from Jesus to a deadbeat dad named Billy. They travel “over dry earth and floods.” And on the mesmerizing murder ballad “Down By the Water,” they drown their own child and blame it on the fish. Harvey, making her first album as a solo artist, comes into her own as a producer, creating atmospheres worthy of these raw, gothic tales. Almost every riff is a simple pentatonic phrase, a shard of the blues poking through the skin of the session. And it’s all in full mourning dress, thanks to slow tempos, low, burbling organs, and heavy swaths of distortion – imagine Violator-era Depeche Mode doing an album of John Lee Hooker covers. “See it coming / At my head / I’m not running / I’m not scared,” she sings, both as a character with a death wish and a songwriter in complete control of her gifts. Our concept of bravery doesn’t always have to be a cowboy perishing in a rain of bullets. It can be an artist doing exactly what she wants.

 

11. Smashing Pumpkins – Siamese Dream (1993)

In the summer of ’96, when Smashing Pumpkins was the biggest band on earth, I saw them deliver an unforgettable set of high-decibel melodrama. During the second encore, the band unleashed “Silverfuck,” the incendiary 8-minute shredfest from Siamese Dream. At the end, instead of smashing his guitar, Billy Corgan sat down on the stage and methodically took it apart, unfazed by the screeching feedback of this little experiment. It’s the perfect metaphor for what made Siamese Dream the greatest LP to ever be labeled “grunge.” Corgan was a neurotic guitar geek, and he used the Siamese Dream sessions to indulge in his obsession, foregoing sleep and the respect of his bandmates to ensure every blast of distortion met with his vision. In the process, he invented his own wall of sound – a steady thrum of multi-tracked guitars that flood our eardrums like bagpipes from heaven. (The only instrument he didn’t personally touch were the drums, probably because Jimmy Chamberlin was one of the best rock drummers on earth in ’93.) Unlike the ragged emotional outpourings coming out of Seattle, this was unapologetically fussy rock music, best experienced on pricey headphones with your eyes closed. Despite the darkness of Corgan’s lyrics – even the hits are cries for help – the majesty of his sonic vision lifts all boats. When he sings, “Today is the greatest day I’ve ever known,” he means the opposite. But the way those guitars ring as they deliver the hook? It makes the line true for me. Like any raging perfectionist, Corgan’s insistence on taking things apart and putting them back together again would come back to bite him. But not before he proved that perfection was within his reach.

 

10. A Tribe Called Quest – The Low End Theory (1991)

In 1991, it was getting harder to disregard rap music as a fad. A year earlier, “Ice Ice Baby” and “U Can’t Touch This” gave the world a preview of the genre’s inevitable crossover dominance. (On the day I’m writing this, 9 of the top 20 songs on the Billboard Hot 100 come from rappers.) A Tribe Called Quest was decidedly not celebrating this. “Rap is not pop / If you call it that, then stop,” scolded rapper/producer Q-Tip on the Queens trio’s second LP. Here were young artists on the cusp of stardom, who had already landed a hit by sampling “Walk On the Wild Side,” abandoning that path and consciously pursuing a different type of hook – anchored in the syncopations of jazz and the pentameters of poetry. “Don’t you know that things move in cycles?” Q-Tip asks his father on his iconic opening verse, openly acknowledging that this new and exciting genre was indebted to the record and book collections of generations past. And with this bold, anthropological mission driving them, Tribe recorded some of the wisest, funkiest, most sweepingly joyful rap songs in history. Tip and the forever-underrated Phife Dawg trade bars about everything from growing up together to dealing with psychotic A&R guys, giving other artists a blueprint for their own careers. They were never pop stars as a result. They’ll just have to settle for being legends.

 

9. Portishead – Live from Roseland, NYC (1998)

Of the handful of James Bond movies I’ve seen, my favorite parts are the songs. A talented vocalist belts their guts out, their voice trembling with emotion, the minor-key arrangement inevitably boiling over with a scalding spray of brass. Then the director credit fades, along with that feeling. Because James Bond is about as passionate as a cold shower. The Terminator feels more. A love of Bond themes was central to the aesthetic of Portishead, the Bristol trip-hop pioneers who combined throwback ’60s horn and string charts with blasts of synthetic noise and head-spinning displays of record scratching.  But it was singer Beth Gibbons that made the trio so much more than a formula. She approached these songs like a self-aware Shirley Bassey, who knows that these intense feelings are unrequited, marveling at the energy she can muster for one so undeserving. And Live from Roseland, NYC is the ultimate document of her achievement. Backed by a full orchestra, which gives Portishead’s ambitiously cinematic sound the dynamic scope it deserves – from whispering strings to trammeling trombones – Gibbons sings with the concentrated energy of a spirit trying to move something corporeal. “I can’t hold this day / Anymore,” she bemoans on “Over,” as a lone guitar delivers a two-note eulogy. By the end of that song, its singer is wailing; the orchestra is at triple fortissimo; the DJ is scratching like there’s bugs in the vinyl. And we are both shaken, and stirred.

 

8. Aimee Mann – Magnolia: Music from the Motion Picture (1999)

The soundtrack album for the film Magnolia – Paul Thomas Anderson’s indulgent masterpiece about the intersecting lives of despairing Californians – contains tracks from four different artists. Yet it’s credited, right there on the cover, to Aimee Mann. This is entirely appropriate, because Anderson has admitted that Mann’s lyrics heavily influenced these stories. At one point, Melora Walters’s character delivers the first line of “Deathly” in conversation: “Now that I’ve met you / Would you object to / Never seeing each other again?” That line is peak Mann, untangling the complicated internal lives of the victimized in a handful of syllables. Like the movie, she makes sure to let pinpricks of hope shine through over the course of nine tracks, making the sadness ring even truer. The richly layered folk arrangements have the color palette of a sunset – nuances of warmth form a halo around Mann’s steady, reassuring voice. And songs like the Oscar-nominated “Save Me” express a stubborn, foundational belief in romantic alchemy – broken hearts can find understanding souls. And when they do, they fuse together to create something new, and strong, and good. The balance of the Magnolia soundtrack is also spot-on – a pair of Supertramp classics about self-actualization and its aftermath; the cheerful self-help R&B of Gabrielle’s “Dreams”; the fairy-tale malaise of Jon Brion’s theme. But this soundtrack belongs to one person, who suspects they could never love anyone, singing songs that will immediately appeal to anyone who ever has.

 

7. Erykah Badu – Baduizm (1997)

When Motown label head Kedar Massenburg introduced the term “neosoul” to describe artists like D’Angelo and Erykah Badu, it was marketing at its emptiest. And most successful. “Neosoul” records, of which Baduizm remains the gold standard, were actually “retrosoul” records – summoning the organic warmth of ’70s Motown while supposedly slighting the slick, rap-influenced R&B that was ruling the charts. It was a white lie to make traditionalists feel like they weren’t out of touch. Lulled by Badu’s nightclub jazz arrangements and laconic, Billie Holiday drawl, they probably never picked up on just how much this Dallas singer, songwriter and iconically headwrapped Soulquarian loved hip hop. “You rush into destruction cause you don’t have nothing left / The mothership can’t save you so your ass is gon’ get left,” Badu sings with the swaggering syncopation of a rapper, on Baduizm‘s first single, “On & On.” This quiet confidence propels her performance throughout, as she dismisses those who dismiss her intelligence, confronts a guy who tries to roofie her, and wrestles with the risks of loving a drug dealer. Her songs and the way she sings them elevate the midtempo jazz vamps that are Baduizm‘s stock in trade. Also like a rapper, she turns to bass lines for guidance, wrapping her syllables around them until they become indelible earworms. In the process, Badu made an intergenerational soul album that reassured her elders, inspired countless rappers, poets and R&B singers, and wove a spell that holds to this day. It was something new, after all.

 

6. Radiohead – OK Computer (1997)

Countless rock bands have written songs about life on the road. Because touring is what bands do, and you write about what you know. But no artist has used their experience on tour to communicate larger metaphors as effectively as Radiohead did on its third album. Singer/songwriter Thom Yorke mined some terrifying and disorienting travel experiences for material, resulting in songs about car and plane crashes, insane thoughts in tight spaces, and grabbing your bags before dawn in a panic. “Transport, motorways and tramlines / Starting and then stopping / Taking off and landing / The emptiest of feelings,” he observes. But this is not an album about airports. By taking that odd sense of disconnection we feel while traveling and applying it to our relationships with our bosses, political representatives, and inner selves, OK Computer tapped into a creeping cultural malaise that would eventually overtake us. Listening today, its themes resonate as strongly as ever, pulled from the brink of fatalism time and again by the music, which is as towering and tender as the band has ever sounded. The six-minute anti-capitalist epoch “Paranoid Android” shifts from buzzsaw guitar screaming to a spine-tingling choral breakdown, giving Gen X its own “Stairway to Heaven” moment in the process. On “Let Down” and “Subterranean Homesick Alien,” Jonny Greenwood’s clean guitar sounds wash over Yorke’s dour observations like cleansing foam. And the arrangement on “No Surprises,” featuring a major-scale glockenspiel loop that could just as easily have been whistled, sounds like brainwashing feels – just a little too perfect. As a result, Radiohead made an album about hopelessness that achieved unforeseen levels of melodic uplift. Like a plane that’s just left the ground, it’s a miracle. One that doesn’t give us much room to breathe.

 

 

 

 

 

 

5. Outkast – Aquemini (1998)

There’s something inherently captivating about duos. Two people whose chemistry is inevitably intertwined with their creations, who push one another to heights they could never achieve individually. It’s why Simon was never as good without Garfunkel. Jack is lost without Meg. And Tip sounds incomplete without Phife.

In 1998, the rap duo Outkast released an album that was about this specific dynamic. They called it Aquemini, a portmanteau of the rapper/producers’ zodiac signs (Big Boi is an Aquarius; Andre 3000 is a Gemini), and proceeded to write songs about the intensity of their friendship and the magic of their chemistry, while exhibiting a zen-like acceptance of its eventual demise. And all of this held water, because musically, these guys were at their absolute peak. They invited live musicians to their Atlanta studio to stretch, deepen and distort their sound, slow-roasting it until any resemblance to East or West Coast rap had sloughed off onto the coals. Aquemini absorbed the sprawling, earthy aesthetic of Parliament-Funkadelic more organically than Dr. Dre’s samples ever could. It set a bar for Dirty South hip hop that has arguably never been cleared. It’s one of the boldest, most self-aware recordings in rap history.

“Stickin’ together like flour and water to make that slow dough / We worked for everything we have and gon’ stick up for / Each other,” proclaims Big Boi on his first verse of the album. The song, ironically titled “Return of the ‘G’,” is a spleen-vent against anybody who was weirded out by Outkast’s 1996 LP, ATLiens (#83 on this list). They’d left the “harder” gangsta rap of their hit debut in the dust, in favor of longer, spacier, more overtly Southern funk experiments. They weren’t pimps anymore. They were aliens. And that was alienating to people who don’t take kindly to change.

“Some of my fashion choices people didn’t accept at the time. I started getting flak from some people, so they were like, ‘Either he’s gay or on drugs,’” Andre shared in an interview. It’s the kind of situation that regularly destroys artistic partnerships – blowback from fans largely directed to one artist, who ends up getting an inordinate amount of attention. Outkast responded by closing ranks.

Aquemini’s lyrical scope is as wide as its sonic palette, including stories about how poverty can strangle hope, detailed deconstructions of failed relationships, and a myriad of ways to let us know why Big Boi and Dre are the type of people that make the club get crunk. But that sense of brotherhood is the common thread, the unifying vision that makes this ambitious, 75-minute album feel not only coherent, but full of exhilarating urgency right up until the last wailing guitar note of “Chonkyfire.” Even the few skippable moments – a pair of skits set in a record store where Outkast haters can’t wait to hear the new “Pimp Trick Gangsta Clique” album – are rooted in the adversity that tempered their bond.

Aptly, it’s on the horoscope-melding title track where everything comes together, and the core ethos of this record is laid bare. Over a syrupy R&B groove where glittering guitar chords can seemingly ring out forever, Andre whispers a chorus about impermanence:

Nothing is for sure
Nothing is for certain
Nothing lasts forever
But until they close the curtain
It’s him and I, Aquemini

Some people use the inevitable end of things as a good reason to give up. This pair of 23 year olds took it as irrefutable evidence that they needed to work even harder. Because the energy created by their duality was special. And thanks to the miracle of recording technology, they had the ability to trap that energy in amber.

Eight years after Aquemini ruled the world, Outkast dropped their clunky film project Idlewild. It was the duo’s first true misstep, and Big Boi and Andre 3000 went their separate ways soon after. They could’ve stayed together and made expertly crafted rap music for years to come. But they could feel that curtain closing. Even when they broke up, they were absolutely on the same page. Today, with popular music an ever-growing cult of personality, there are very few duos making noise. But we can still press play on Aquemini and sit in wonder of what can happen when two driven, talented individuals find inspiration in one another.

4. Elliott Smith – XO (1998)

There’s a generally agreed-upon theory when it comes to vocal harmonies – nothing sounds better than two blood relatives singing together. And there’s a bevy of DNA-sharing crooners to back up this “blood harmony” argument (e.g. the Everlys, Andrewses, Wilsons). But in 1998, Elliott Smith released an album stuffed with dazzling vocal harmonies, without a family member on hand. It was perhaps a depressing exception to the rule. Because the only person this artist wanted to sing with was himself.

After releasing a trilogy of quietly devastating folk albums on indie labels, Smith unexpectedly blew up when director and fellow Portlander Gus Van Sant caught wind of him, using six of his songs on the soundtrack to his movie about how hard it is to be a handsome white genius, Good Will Hunting. The track “Miss Misery” got an Oscar nomination alongside the likes of Celine Dion and Faith Hill. And Smith performed it on the telecast, with artfully mussed hair and a white suit, looking tentative but sounding absolutely at home with the melodic flourishes of the pit orchestra.

After this unforeseen dalliance with the mainstream, it was time for Smith to make good on all the attention, and elevate his game in the recording studio. He was more ready than it may have seemed. The singer/songwriter’s willingness to sound vulnerable on tape didn’t mean he didn’t know how to take control – he spent five years leading the alt-rock band Heatmiser, which landed a contract with Virgin in 1996, right before Smith’s solo career became too big to ignore. So while the songs on XO are rooted in feelings of inadequacy, the arrangements are the work of a confident artist coming into his own.

Take the bridge of XO’s first single, “Waltz #2,” for example. The song is a poetically veiled story about Smith going to a bar karaoke night with his mom and stepfather. He no longer recognizes her, and tries to brush off being triggered by him. All over a waltz tempo sprinkled with rickety saloon piano runs. Which builds to the bridge, a heartbreaking sigh of resignation:

I’m here today and expected to stay
On and on and on
I’m tired

Musically, Smith treats this moment like a rocket launch. The band revs its engines to the first line. Then his multi-tracked vocals reach higher and higher with each ensuing “on.” As we arc back down to earth, our narrator might be tired, but us listeners are inspired. XO is loaded with dissonant moments like these, beauty and sadness spiraling into one another until they’ve bonded. It’s a forensic analysis of what a big fucking mess life can be, delivered in perfect pitch.

All of it is anchored by Smith’s underrated guitar playing. Years spent recording alone into four-tracks honed his chops to the point where he could play the chords, bass line and lead melody simultaneously, giving himself and co-producers Rob Schnapf and Tom Rothrock fully formed blueprints to build on. The opening “Sweet Adeline” relies on little more than his bouncing acoustic melody for a full 90 seconds, before the dam breaks and the drums, piano and backing vocals drown us. And his finger-picked intro to “Independence Day” is so deeply, fluidly melodic, it could’ve worked as an instrumental.

But that first blast of full-bore instrumentation in “Sweet Adeline” showed us that XO was not going to be another tape-hiss-heavy, stripped-down affair. Smith, an avowed Beatles fan, was ready for his big, Revolver-style, studio-driven artistic evolution. And he sealed the deal with an album closer that’s every bit as jarring as “Tomorrow Never Knows.”

“I Didn’t Understand” finds Elliott Smith alone. No instruments, no guest vocalists, a lyric sheet that gives him nowhere to hide. The only sound is his voice, stacked to the heavens in an audacious display of vocal harmony. It begins with yet another majestic sigh, a parishioner in a confessional clearing his throat before laying himself bare. And then he begins, singing in his uniquely cryptic way about a breakup, mostly about how much he deserved it:

And so you’d soon be leaving me
Alone like I’m supposed to be

Then, with the vocals-only arrangement underlining the stakes – intricate waves of beauty when he exhales, nothingness when he inhales – Smith ends his song with a stanza that will crush anyone who has been too stupid or self-absorbed to realize that somebody was right there in front of them, needing them:

You once talked to me about love
And you painted pictures of
A Never Never Land
And I could have gone to that place
But I didn’t understand

A short five years after XO cemented his genius, Elliott Smith left us. But not before he showed us how beautiful it can be to create your own sense of harmony.

3. A Tribe Called Quest – Midnight Marauders (1993)

Sometimes things align in just such a way. You encounter a work of art at the perfect moment, when the context of your reality leaves you especially open to its aesthetic. There’s a grand interlocking of gears. And this creation forever becomes a part of you.

A Tribe Called Quest’s third album, Midnight Marauders, was the first rap CD I ever bought. Up till that point I had been thoroughly ignorant of any genre that wasn’t rock, thinking Led Zeppelin and Metallica were all I would ever need. Luckily, some new friends with better taste entered my life. One of them played Tribe’s deliriously fun crew single “Scenario” for me, and in that moment I was given permission to pursue so much more in my BMG Music Service orders – artists that put rhythm first, that interpolated the history of jazz and funk and R&B and rap into something exhilaratingly new, that put an absolute premium on cleverness.

So Midnight Marauders arrived at the precise moment where I was ready to expand my definition of what music, and friendship, could be. It featured two rappers, Q-Tip and Phife Dawg, who had been BFFs since they were two years old, and had the chemistry to prove it. Tip’s smooth-talking philosophy gelled with Phife’s raspy underdog humor in a goosebump-raising way – the energy they created on tape together transcended mere artistic talent. These guys loved and needed each other, and they never sounded happier to be trading bars together than they did on this album. Factor in the panoramic, viscerally funky productions from Tip and DJ Ali Shaheed Muhammad, and you’ve got music that hums with powerful, positive vibrations. It was the lightning bolt that knocked me off my rockist donkey for good.

And this record doesn’t just loom large in the context of my mundane life story. It holds a place in the history of rap as a beacon of brotherhood, shining brightly at a time when the battle lines between East and West Coast hip hop were being drawn. For the album cover, Tribe reached out to rap artists across the country, asking for a headshot of them wearing headphones. Dr. Dre is on there, along with Sean Combs, Chuck D, Ice T, the Beastie Boys, Souls of Mischief, MC Lyte, and dozens of others. It’s a testament to the unifying power of good music, and the perfect visual accompaniment to the infectious camaraderie that takes these particular songs over the top.

Midnight Marauders begins with two songs that celebrate how much fun it is to make music with friends, and then share those creations with the world. The first, “Steve Biko (Stir It Up),” shouts out the trio’s Queens roots over a fluttering Woody Shaw sample. Phife fully embraces his “Five Foot Assassin” persona for the first time here, “knocking fleas off his collar” with wise-cracking ease. Tip ends the track on a beautifully introspective tear:

Ok, I am recognizing that the voice inside my head
Is urging me to be myself but never follow someone else
Because opinions are like voices, we all have a different kind
So just clean out all of your ears, these are my views and you will find
That we revolutionize over the kick and the snare
The ghetto vocalist is on a state-wide tear

Then comes “Award Tour,” a laid-back chronicle of the bonds formed by travel, where guest rapper Trugoy of De La Soul uses each chorus to check off cities around the world that have been lucky enough to watch Tribe represent. As Weldon Irvine’s irresistible electric piano loop takes the track airborne, Phife provides some ballast with one of his greatest verses – outlining the superior nature of his skills, the philosophy of Tribe’s music, and the bone-deep quality of his friendships, all with a wink and a smile:

So Shaheed come in with the sugar cuts
Phife Dawg’s my name, but on stage, call me Dynomutt
When was the last time you heard the Phife sloppy
Lyrics anonymous, you’ll never hear me copy
Top notch baby, never coming less
Sky’s the limit, you gots to believe up in Quest
Sit back, relax, get up out the path
If not that, here’s a dance floor, come move that ass
Non-believers, you can check the stats
I roll with Shaheed and the brother Abstract

This same formula is perfected across every track of Midnight Marauders. Even the short skits (one of the few things about ’90s rap that I don’t miss) support the album’s refreshingly unpretentious, all-you-need-is-a-dance-floor philosophy. In a spoof of humorless robocall voices, the album’s electronic narrator interrupts the proceedings from time to time, to deliver various messages: She tells us the names of the band members, suggests that education is the best way to combat the AIDS crisis, and lets us know what BPM levels to expect. Perhaps most appropriately, she pops in at the end of the drum-heavy classic “Clap Your Hands” with some advice that could very well be this album’s mission statement: “Keep bouncing.”

2. Wu-Tang Clan – Enter the Wu-Tang: 36 Chambers (1993)

From 1984-87, a sci-fi adventure cartoon adapted from a Japanese anime series became a hit in syndication. It told the story of five young pilots defending their planet from the armies of an evil alien king. When things got especially perilous, these soldiers would literally unite – their lion-shaped planes locked together to form a giant, sword-wielding robot called Voltron.

The nine members of the Staten Island rap crew known as the Wu-Tang Clan would have been teenagers when Voltron was on the air. And being the innately talented storytellers that they were, they absorbed the show’s messages about the power of togetherness, of how courage under fire can grow exponentially when it’s shared. When it came time for them to hole up in a tiny studio and knock out their debut album, they kept their egos in check. Even though the odds were against them ever getting another chance at fame like this, eight mega-talented rappers uniformly agreed to let their producer/bandleader RZA make the final decisions on whose verses made it in. If the results of these sessions achieved mere coherence, it would’ve been an achievement. But Enter the Wu-Tang: 36 Chambers is one of the most focused, balanced LPs in rap history. Its off-the-charts energy hits as hard as it does because of how expertly it’s been channeled. Every single outsized personality gets his moment in the sun, without one rhyme, sample, or snippet of kung-fu movie dialogue ever feeling extraneous. This wasn’t just the debut of a new artist. It was the invention of a myth. One album in, and Wu-Tang had slain the king.

In hindsight, ceding artistic control to RZA was the smartest thing these guys could’ve done. He was in the midst of developing a signature sound built on martial drums and sped-up soul samples, with just enough grit in the mix to make it sound like a rare find at the bottom of the bin. His productions ran the gamut from rugged to rollicking to rueful – and he had a cast of characters to suit any mood. So the confrontational, elephantine drums of “Bring Da Ruckus” sound like they were tailored bespoke for Ghostface Killah’s hyperactive, ultraviolent style. “Shame On A N—a,” with its catchy R&B horn breaks, is the ideal showcase for Ol’ Dirty Bastard’s wild, oxygen-sucking wisecracks. And the wistful, Gladys Knight-sampling ballad “Can It Be All So Simple” gives Raekwon a rain-spattered backdrop that perfectly frames his gritty childhood reminiscences. It’s incredibly rare to encounter a debut album that covers such a wide swath of emotional territory.

Part of it was timing. These guys had been rapping all their lives, scribbling in notebooks, developing their characters, discovering their flows. And here they were, getting their shot, over some of the nastiest beats ever created. (This was technically RZA and GZA’s second shot; both of them had brief, pre-Wu solo careers under different names.) The energy in their voices is palpable. Which meant they could compare themselves to cocaine straight from Bolivia, or threaten to kill you while making a Family Feud reference, or dip into a couplet from Green Eggs and Ham, and it all would feel like it was shot straight from a cannon into your adrenal glands.

Once Enter the Wu-Tang established them as visionaries, the members of Wu-Tang would go on to create hours upon hours of legendary, boundary-pushing hip-hop, most of it on their own solo albums. But they never could reach the heights they achieved when they were young unknowns, hungry as hell and utterly in it together. “So when you see me on the real / Formin’ like Voltron / Remember I got deep like a Navy Seal,” warns Raekwon on “Shame on a N—a,” evoking that larger-than-life cartoon machine that ran exclusively on human bonds. It’s a perfect metaphor, one of many on this flawless, unflagging LP. Because when Wu-Tang Clan first formed, it was into a shape that has yet to be replicated.

1. Björk – Post (1995)

It’s hard enough for an artist to sound ahead of their time. But on Björk’s second album as a solo artist, she was ahead of her time, and behind it, and looping back through it like a reincarnated spirit, and angling jagged shards of it at the sun to melt away whatever barriers we thought existed between post-punk balladry and thrumming house beats and musty old showtunes.

The Icelandic singer/songwriter and ex-Sugarcube had already taken some gargantuan strides on 1993’s Debut, using her newfound artistic freedom to see how her operatic supernova of a voice held up in a variety of contexts. That album crackles with experimental energy, and the growing confidence of a superhero who’s just starting to understand how much power she really has.

If Post merely kept this feeling going for another album cycle, it would have been a worthy achievement. But a lot had changed in the artist’s life in those two intervening years. As her star rose, she relocated to London, a global hub for pop-adjacent, emotionally complex club music. From this new, rain-spattered catbird seat, Björk approached the Post sessions with an auteur’s vision and an ice climber’s confidence, taking over lead production duties for the first time in her career. And to make it absolutely clear how much we were about to be blindsided by her evolution, she kicked off the record’s debut single with the sound of a fiery explosion. “Army of Me” is one of the all-time gauntlets thrown in the history of pop music – right at that precise moment when this buzzy alternative artist was primed to reach unforeseen levels of popularity, she hurled a ball of fire right down the throat of Generation X. As the distorted circular bass line slithers its way through one of the best-ever interpolations of John Bonham’s “When the Levee Breaks” beat, Björk drops bombs on slacker-chic culture, a full decade before it metastasized into the YouTube commentariat:

You’re alright
There’s nothing wrong
Self sufficiency please!
And get to work
And if you complain once more
You’ll meet an army of me

With the sheer snarling force of “Army of Me” as its opening salvo, it’s clear that this record is going to have plenty to say about the burgeoning self-confidence of an artist coming into her own. The sonic palette expands to encompass an entire Pantone book – the fluttering acid house drums of “Hyperballad”; the soft, cinematic strings of “You’ve Been Flirting Again”; the fire-breathing horn section of “I Miss You”; the cheeky, zing-boom Broadway orchestra of “It’s Oh So Quiet.”

Lyrically, Björk is just as ambitious, bending time and space to suit her mood. “I miss you, though I haven’t met you yet,” she tosses off, sounding not like a lonely person searching for hope, but like a traveler from the future with otherworldly insights on her fate. “Hyperballad” details how amazing it feels to crawl into bed beside someone you trust by focusing on what happens before that moment – the narrator stands at the top of a mountain, dropping things off the edge and watching them break, in order to fully appreciate her safety. And over the gritty, churning bass of “The Modern Things,” the most visionary artist of the ’90s talks about technological innovations like they’re buried treasure, just waiting for a truly special human being to unearth them:

All the modern things
Like cars and such
Have always existed
They’ve just been waiting in a mountain
For the right moment
Listening to the irritating noises
Of dinosaurs and people
Dabbling outside

In 1995, Björk had this treasure map. And she was well aware of its power. She called this album Post to create a clear delineation line between it and Debut – an overt “before” and “after.” It’s a grand, futuristic promise of artistic evolution, and Post makes good on it in ways that I am still processing 25 years later. Feeling free to explore whatever sounds, subjects and potential collaborators were fascinating to her in that moment, Björk made a record that is post-modern, post-punk, and post-linear. It was ahead of its time then, and still is now, and will be until the seas swallow us whole.