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.

Here’s the eminently funky “Spoon.” Feel free to cut a rug, or freak dance, or whatever the kids are calling it these days.

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.

Step into the shoes of a sensitive, creepily possessive dude, with the jazzy acoustic ballad “Am I The Only One?”

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.

“Pyromaniax” is the quintessential Arsonists song for sure, but my favorite is “Backdraft,” a powder keg of NYC hip-hop that storms out the gate, and impressively, never flags.

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 juvenile 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 started to lose the magic I so resolutely believed they had when I was 16. But Boys For Pele holds a shadow of that mystique to this day, possessing everything that the artist does best – complicated clusters of piano and harpsichord notes, seriously 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 heavily 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.” Most importantly, as a player, Amos is at her best here, keeping the show-offy passages to a minimum and letting the chords do their thing. I still look at it with more nostalgia than anything else, but in the context of all the boring dance tracks, labored literary references and bat shit characters that followed it, Boys For Pele has aged pretty darn gracefully.

“Little Amsterdam” is my favorite cut here, if only because it shows how good Amos could be when she kept things simple.

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.

“Hell Of A Hat” isn’t the best complete song on the record. But that horn part. Damn.

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.

Of all the examples of Eminem’s singular talent in evidence here, the purest is “Brain Damage,” which shows the artist was at his best in the role of bullied outcast.

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.

And after all that raving about UO’s manly swagger, I’ve gotta go with “Dropout” as my favorite Saturation track. A stripped-down plea to get away from a life of hanging out in Dairy Queen parking lots, it stands out like a nightingale in a biker gang.

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.

If I hadn’t played the title track to death over the years, it would be my choice here. Hence, I’m picking the harrowing, slinky “Babylon,” which finds Andre 3000 rapping about being born addicted to coke, and Big Boi struggling with Catholic guilt.

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.

When Emmylou sings Welch’s “Orphan Girl,” the heartbreak of it all is almost too much to bear.

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.

Here’s “Wiser Time,” a lazy river of a country-rock song with a great, cowbell-inflected beat.