49. My Morning Jacket – Evil Urges (2008)
Before Evil Urges, listening to My Morning Jacket was like getting slowly drunk on a great bottle of wine, without the crusty red lips and ungodly hangover. Jim James’ voice is somewhere in between Neil Young and a member of the heavenly host, and on his band’s early records, it took their psychedelic-country-rock sound to spine-tingling heights. But here, James uses his unique timbre to get a little freaky, employing his falsetto with relentless glee on the Tone Loc-meets-Prince jam “Highly Suspicious.” While that cut is the most jarring departure, the rest of Evil Urges provides more telling evidence of the band’s evolution – MMJ now prefers a well-crafted pop sheen to that old Crazy Horse jangle.

48. Shelby Lynne – I Am Shelby Lynne (2000)
It was only 25 days into the 2000s, and the contemporary country music of the decade had peaked. After kicking around Nashville for a decade or so, Shelby Lynne struck gold with her sixth album, which didn’t just show that country-pop could sound organic, warm and seductive, but also positioned the singer/songwriter as the heir apparent to Dusty Springfield. These are the kind of songs Sheryl Crow wishes she could come up with – especially the tear-streaked, girl group R&B of “Your Lies,” the Bonnie Raitt-ish phrasing and impeccably arranged horns of “Why Can’t You Be,” the sweet, nostalgic soul of “Where I’m From.” The record earned her a much-deserved Grammy, but it was for Best New Artist, proving that the Grammys are run by ignorant puds.

47. Whiskeytown – Pneumonia (2001)
For the first half of the 2000s, Ryan Adams couldn’t stand the heat, but remained firmly in the kitchen. His promising 2000 solo debut, Heartbreaker, started the hype train rollin’, and by the time Gold came out a year later, Adams seemed to have all of singer/songwriter-dom on his jean-jacketed shoulders. It was all downhill from there – the guy released seven albums from 2000-2005, preferring to be prolific instead of good. And through it all, this album, the third and final release from the Adams-led alt-country juggernauts Whiskeytown, was lost in the shuffle. Full of the heartfelt ’70s AM pop that marked Adams’ best solo albums, as well as the swirling fiddles and steel guitars of band members Caitlin Cary and Mike Daly, Pneumonia is a real masterpiece. It’s joyful, sad, ingratiating and experimental, and proof that Ryan Adams has chops indeed.

46. Sparklehorse – It’s A Wonderful Life (2001)
At first blush, this album has one of the most sarcastic titles in rock history. Sparklehorse records were never all that positive before this one, but It’s A Wonderful Life finds Mark Linkous taking his fragile, lo-fi songs to newer, weirder depths of despair. But Linkous isn’t one to joke, and after living with this album for close to a decade, the streaks of hope are easy to spot, like drops of glitter glue on black construction paper. The earnest whisperings of the title track aren’t ironic – when Linkous compares himself to a dog that ate your birthday cake, there’s plenty of self-loathing going on, but also a sense of appreciation for how it feels to be alive, running free with frosting in your hair.

45. Portishead – Third (2008)
For better or for worse, much is made about the amount of time it takes for a band to make an album – if it’s quick on the heels of a previous release, we tend to expect something rawer and more “real;” if it’s 11 years between records, we tend to expect a Chinese Democracy-level disaster. But with Third, trip-hop pioneers Portishead exposes these critical expectations as hogwash. Their first studio album since 1997 is a natural progression of its sound, not some overproduced, micro-managed bomb. You could say that the album has more “trip” than “hop,” eschewing the turntable theatrics of yore for even moodier electronic and post-punk panoramas. Beth Gibbons’ voice is as hauntingly beautiful as ever, whether it’s navigating through the drum-loop explosions of “Machine Gun,” the space-folk picking of “The Rip,” or the subterranean ukulele vignette “Deep Water.” This is music that’s worth any kind of wait.

44. Grizzly Bear – Yellow House (2006)
Dreamy, hyper-vocalized folk music ain’t just for hippies anymore. Or at least this album ain’t – a gorgeous, ethereal platter of plaintive acoustics and reverberating harmonies with roots in CSNY and aspirations towards outer space. Grizzly Bear’s second LP might not have been the record that got them noticed on a grand scale, and that’s probably fitting. Where 2009’s Veckatimest finds the group reaching even higher, Yellow House is a humbler attempt at fusing ’60s pop and country with a flair for spaciness that makes the band an organic American counterpoint to Radiohead. That’s high praise, indeed, but when the swirling, atmospheric vocals of songs like “Knife” float through your headphones, you’ll understand how much Grizzly Bear deserves it.

43. Madvillain – Madvillainy (2004)
MF Doom’s second appearance on this list is for this project with the omnipresent producer Madlib – the pair has piles of excellent tracks to their credit individually, but Madvillainy is the high watermark of both of their careers. Madlib’s beats are deliciously strange throughout – a fusion of campy lounge charts, crunching drums and hissing vinyl noise – and Doom nestles into them like they’re his childhood bed, using his comic book obsession to inspire superhuman verses that often comprise entire tracks. With most of these cuts coming in under the two-minute mark, Madvillain is able to overstuff this disc with eccentric grooves and unforgettable plays on words. For fans of smart, boundary-pushing hip hop, spinning Madvillainy for the first time must be somewhat akin to finding the Holy Grail.

42. Ed Harcourt – Here Be Monsters (2001)
There’s no doubt about it – Ed Harcourt’s favorite Beatle is Paul. As the singer/songwriter/shameless over-emoter’s career took flight in the 2000s, his best work was full of the Cute One’s head-over-heels-in-love themes, executed in a pretty, irony-free way. His best work being this album and little else, unfortunately. The kaleidoscopic productions that followed Here Be Monsters tended to be too rich for even a Wings fan’s blood, suffocating Harcourt’s sweet sentiments under merciless strings and long, meandering constructions. Given this context, Harcourt’s first proper album sounds all the more endearing, using piano, trumpet and the occasional orchestra to deliver his tender, desperate love songs. It’s one blissful pop moment after another, the kind of transportive album where the refrain “You’re the apple of my eye” feels heartfelt, and not the least bit cheesy.

41. Scott Walker – The Drift (2006)
Halloween is approaching as I write this little review – the perfect time of year to shut off the lights, put The Drift on repeat and let your head fill up with nightmares. A death-obsessed collection of avant-cabaret dirges, Scott Walker’s 13th album is utterly unrelated to his most famous work, crooning ’60s pop hits like “The Sun Ain’t Gonna Shine Anymore” as the leader of The Walker Brothers. The Drift is marked by murky, unpredictable atmospheres, sickly, dissonant strings and stabbing notes that shock you out of your seat with slasher-film quickness. Walker writes lyrics about Benito Mussolini’s assassination and Elvis Presley’s stillborn twin brother, and sings them with operatic intensity. It’s as disturbing as music gets, short of a Dave Matthews concert.

40. PJ Harvey – Stories From The City, Stories From The Sea (2000)
On her essential ’90s albums, Rid of Me and To Bring You My Love, PJ Harvey could have gotten along on persona alone. Of course, whether she was playing the role of furious punk visionary or Nick Cave-ish chanteuse, she always had fantastic songs and a raw, singular style to back it up. On Stories From the City, Stories From the Sea, she put her image on the back burner and relied exclusively on her chops. As a result, we got a dozen focused tunes that manage to the most universally appealing of her career, without compromising her trademark mix of determined riffs and dramatic vocals. “Big Exit” is the kind of song she can write in her sleep these days, with two churning chords and a fatalistic narrator; the Thom Yorke duet “The Mess We’re In” is as spellbinding as you’d expect, and the muted ballad “Beautiful Feeling” is a thoroughly convincing expression of love’s exhilarating sting.

39. Elliott Smith – Figure 8 (2000)
This album closes out one of the most heartbreakingly brilliant trilogies in folk-rock history, made all the more poignant by the fact that it’s the last Elliott Smith album to be released during the singer/songwriter’s life. The death of an artist can make you look at his or her former work in a different light, but with Smith, the knowledge of his intensely personal demise didn’t really add anything to the experience. It’s intensely personal songwriting, after all, and Figure 8 is marked by the grim acceptance of a lonely future. An ex-lover is “just somebody that I used to know.” When “everything reminds me of her,” it’s something that happens in spite of the narrator’s best efforts. Hell, there’s a song called “Everything Means Nothing To Me.” Smith continues down the lushly produced path that he mastered on 1998’s XO, and while you can make the argument that these two albums aren’t as intimate as his beloved Kill Rock Stars recordings, I’ll take this mixture of pain and pleasure every day of the week.

38. Lil Wayne – Tha Carter III (2008)
It was easy to criticize mainstream hip hop in the 2000s, with artists like Nelly, Soulja Boy and 50 Cent offering up endless fodder. But you needed huge blinders to ignore all the great popular rap that this decade gave us, including Tha Carter III – that rare massive hit album that deserves every penny it earned. This sprawling, narcotic masterpiece is equal parts swagger, crass materialism and soul-searching introspection, and it brought Lil Wayne to the elite level of the artists that he neurotically name-drops – Jay-Z, Andre 3000, Biggie, etc. Full of woozy humor, ridiculous egotism and surprising tenderness, Tha Carter III pairs the emcee’s seemingly top-of-mind observations and smoke-ravaged voice with an impressively eclectic stable of beats – the chipmunk soul groove of “Mr. Carter,” Robin Thicke’s sexy guitar lick on “Tie My Hands” and the otherworldly keyboards and pounding drums of “Phone Home” being the most transcendent. Forget how frickin’ popular the thing was; it’s the defining moment of one of the boldest, most entertaining voices in modern hip hop.

37. Outkast – Speakerboxxx/The Love Below (2003)
Of all the great singles that were released in the 2000s, a disproportionate amount of them were hip-hop or R&B tunes. And while Kanye West has a legitimate claim to the “singles king of the decade” title, my vote would go to Outkast. Faced with the unenviable task of following up Stankonia, Andre 3000 and Big Boi thought big, putting together a double album, with one disc each to reflect their distinct personalities. It’s not as good as its predecessor, but then again, few things are. And it has some unbelievably infectious cuts – “Hey Ya” is that rare pop masterpiece that can never be overplayed; “Unhappy” is an airy, irresistible R&B groove that fits beautifully with its “might as well have fun” philosophy; “She Lives In My Lap” is a sea of synthesized eroticism that would make Prince proud. Dre’s The Love Below side is as adventurous as expected, mixing jazz crooning, drum and bass instrumentals and synth-funk jams with aplomb, and Big Boi’s Speakerboxxx is less ambitious and more cohesive, boasting some masterfully slick funk jams and those trademark machine gun rhymes. This could end up being the last great Outkast album. But it’s going to be a hell of a long time before it gets old.

36. The Weakerthans – Reunion Tour (2007)
I often find myself loving a sad movie, and then vowing never to see it again. Wouldn’t there be something wrong with a guy that wanted to watch Vera Drake over and over again? Perhaps wussy, emotional rockers are more my thing, but the music of The Weakerthans possesses the kind of sadness that I can’t get enough of. And this Winnipeg band’s most recent record is their most triumphant achievement, 11 tracks that look at life and love through the panes of a rain-spattered picture window. John Samson’s lyrics are as poignant as ever, sympathizing with cryptozoologist crackpots and aging ex-goaltenders, and exploring feelings of uselessness through a housework metaphor that’s just heartbreaking. I’ve painted an awfully morbid picture here, but these songs are also full of excellent hooks – Reunion Tour gets you humming along to themes of introspective turmoil. And “Utilities,” that song about uselessness, features what might be the most emotionally effective guitar solo of the decade.

35. The White Stripes – De Stijl (2000)
Led Zeppelin did some mind-blowing stuff once they spread their wings in the early ’70s and looked beyond the raw blues of their first two albums. But they also never rocked harder than they did in the early days. You can draw a pretty fair parallel to The White Stripes in this decade, a band that blew us away with two threadbare indie-blues-rock masterpieces, then went on to a slightly more polished sound and loads of success. So for all of the wonderful work that Jack and Meg did after this album and White Blood Cells, these records remain the essence of what makes them great. And De Stijl is the best of the best, because it’s almost completely unadorned, relying on a few chords and loads of guts to connect with listeners, and succeeding on every single track. The guitar playing on cuts like “Hello Operator” and “Death Letter” is blisteringly good, and “Apple Blossom” is an ingenious pop song about love’s therapeutic power – like Zep’s “Black Mountain Side,” it’s just the kind of out-of-leftfield brilliance you’d expect from a young band poised to take over the world.

34. LCD Soundsystem – Sound of Silver (2007)
Imagine if David Byrne was never seduced by the melodies and rhythms of world music, and had an affinity for club jams instead. You’d get something approximating LCD Soundsystem, the brainchild of singer/songwriter/beat-maker James Murphy. On his second album, Sound of Silver, Murphy shows us just how emotionally and sonically riveting electronic music can be, layering subtly catchy melodies over head-trip productions like the sublime one-two punch of “Someone Great” and “All My Friends.” And his lyrics are up to the challenge, dealing with the loss of a loved one on “Great,” and the sobering onset of adulthood on “Friends.” Then there are the fantastic dance-punk grinders he’s known for, like “North American Scum,” and the clever, Beatlesque closer, “New York I Love You, But You’re Bringing Me Down.” If there could somehow still be electronic music naysayers out there, this is the album that will shut them up, once and for all.

33. Andrew Bird & The Mysterious Production of Eggs (2004)
It’s a nifty little feat for an artist to be both accessible and undoubtedly unique, and Andrew Bird has fit both descriptions since his days fronting the Bowl of Fire, whose excellent 2001 album The Swimming Hour missed this list by a hair. The singer, songwriter and violinist has really come into his own since going solo, however, and The Mysterious Productions of Eggs is the high watermark of this fruitful era. This is the perfect mix of Bird’s whimsical and adult alternative sides, a tapestry of weird, gorgeous songs about nervous tics, psychological diagnoses of children, birthdays and opposite days. The violins swirl and the guitars build, and Bird’s heady couplets seal them together with SAT words that are as beautiful as they are cerebral. Chill-inducing stuff, all of it.

32. Neko Case – Middle Cyclone (2009)
Neko Case’s fifth album finds her at the peak of her abilities, channeling Emmylou Harris and Jeff Tweedy in her reverb-laden alt-country soundscapes, and the devastating power of Mother Nature in her lyrics. When a singer/songwriter name-checks the natural world, we expect it to be a treatise on peace and beauty. But on Middle Cyclone‘s opening cut, “This Tornado Loves You,” the narrator is a fearsome storm, destroying towns and villages in her search for the love that got away. The lilting Sparks cover “Never Turn Your Back On Mother Earth” turns the tables on the standard abuser-victim relationship between mankind and the environment. On the title track, Case lets her guard down to confess the pain of a loveless life, but she finds her strength by the end – “But I choke it back/How much I need love.” The record is a gorgeous examination of love’s warts and blossoms, and by the time you get to its final cut – more than a half-hour of cricket-laden nature sounds – it feels less like a soothing sleep aid and more like a beautiful, potential threat.

31. Jill Scott – Who is Jill Scott (Words and Sounds, Vol. 1) (2000)
Music didn’t get more soulful in this decade than on Jill Scott’s debut album, a passionate, organic slab of R&B tinged with hip-hop, funk and spoken word. Whether she’s proselytizing about great food (on the magnificent extended jam “It’s Love”) or discovering a boyfriend’s infidelity (the clever poetic interlude “Exclusively”), Scott makes a personal connection to the listener. This is not a pop album by a worship-seeking diva; it’s real stuff, delivered with the honesty, fallibility and raw talent of a real artist. All of the genres tapped here are clearly beloved by the singer/songwriter – soul/hip-hop hybrids were big sellers in the 2000s, but Scott’s rap cred is as legit is gets. (She co-wrote “You Got Me” with The Roots, for Chrissakes.) It all just adds to that feeling of realness. The artist’s voice is unnaturally powerful, to be sure, but when she invites us to take a long walk, it feels as familiar as an old friend.

30. Kanye West – Late Registration (2005)
The reactions that I’ve heard to Kanye West’s latest ill-advised award show stunt have been disconcerting. Sure, it made him look less than dignified. But I get the feeling that people are rejoicing in his embarrassment – Jay Leno brought up his recently deceased mother in an interview with West, a pathetic attempt at a Hugh Grant redux that some folks I know thought was just awesome. I think some people have had animosity towards West since his brilliant Katrina-era Bush bashing incident, and now that they have something they can outwardly criticize that doesn’t make them look racist, they’re going to make the most of it. Me, I’m going to dig even deeper into his music, which injected some much-needed emotion and sensitivity into mainstream hip-hop, paired with some of the greatest productions that the genre has ever seen. Late Registration cemented West as a superstar, thanks to the ingenious “Gold Digger,” but there’s a lot of pain and introspection here too, like the hospital waiting room poetry of “Roses” and the parental appreciation jam “Hey Mama.” As the second installment of his higher education-themed trilogy, the album finds the artist in the middle of an especially confusing and rewarding semester – full of unbelievable success and all the self-doubt that comes with it. And it’s this kind of honesty that will keep West’s music interesting and universally palatable, no matter how many teenybopper speeches he interrupts.

29. Aesop Rock – Labor Days (2001)
When you’re a rapper with incredible command over an expansive vocabulary, it’s gotta be tempting to stuff every millisecond of your songs with syllabic fireworks. Aesop Rock is such a rapper, and on his first album at least, he managed to keep his powers in check enough to make a real masterpiece. Oh sure, Labor Days is lyrics-first hip-hop, all bizarre metaphor and spacey simile, but there are also some tight, unforgettable message tracks here that prize story over vocab – the follow your dreams tale “No Regrets” and the take this job and shove it mantra “9 to 5ers Anthem” being especially effective. The MC went on to become a victim of his own verbosity on later records, but not before giving us an independent hip-hop classic.

28. Amy Winehouse – Back To Black (2006)
Everyone loves to hear stories about the tragically talented. And while I’m not writing off Amy Winehouse to the point of lumping her in with Joplin and Hendrix – she could still have a very long and fruitful career, after all – there’s no doubt that she was the most gifted artist of the 2000s to get more attention from the tabloids than anywhere else. Of course, none of Winehouse’s extra-curricular activities matter unless you’re a friend or family member. What’s worth discussing is this, her second album and ticket to worldwide acclaim. Back To Black didn’t just take listeners by storm with its mascara-streaked mix of girl-group pop and last call laments, it inspired a mini retro revolution of copycats, both respectable (Adele) and forgettable (Duffy). These are songs about loneliness, regrets and drunken mistakes, dressed up in Phil Spector’s finest duds and sung in Winehouse’s deep, earnest tenor. Whether you’ve screwed up your life or just want to sing along to a killer groove, this is ideal stuff.

27. Common – Be (2005)
In 2005, Kanye West released his triumphant Late Registration album, a thoroughly pleasing listen for both snotty critics and folks who just want the singles. But in the same year, another Chicago MC released a record that was tighter and even more soulful than said smash. Be was the follow-up to Common’s sprawling, psychedelic experiment, The Electric Circus, and in this context it’s a lean, mean, head-bobbing machine. It’s as focused as the rapper has ever been – even the excellent Like Water for Chocolate got fanciful at times, and none of Be’s 11 tracks meander, including the eight-minute closer “It’s Your World/Pop’s Reprise,” which features the MC’s father delivering some thought-provoking poetry about the understanding of self. From the sweet eroticism of “Go” to the courtroom soap opera “Testify” and the monogamy shout out “Faithful,” every song is what it is, coupling effective storytelling with beautifully interpolated classic soul samples. It’s Common’s ultimate achievement – a hip hop album that nourishes you from head to toe.

26. Blackalicious – Blazing Arrow (2002)
Blackalicious is a group with major weapons, and on its second album, they’re straight-up deadly. The California duo’s one-two punch of rapper Gift of Gab and producer Chief Xcel is as good as it gets on Blazing Arrow, a record that captures the MC’s unbelievable speed and dexterity without getting too wordy and features some wonderful, eccentric sample choices from Xcel. Like the title track, for example, which repurposes the chorus from Harry Nilsson’s “Me And My Arrow” to create an entirely unique bit of avant pop-rap. This is followed by the stunning, ominous “Sky Is Falling,” which features a chorus of female vocalists detailing disasters to come – a bone-chilling, hip-hop take on The Furies. Gab and Xcel refuse to stick to one mood or texture throughout, going from ultimate feel-good anthems (“Make You Feel That Way”) to battle rap exercises (“Chemical Calisthenics”) without worrying too much about padding the transitions. It’s a cornucopia of vibrant, first-rate hip-hop, an adventure of a listen from track one to 17.

25. Feist – The Reminder (2007)
Forgive this paraphrase of an Everly Brothers/Orbison/Nazareth classic, but love aches. And nothing was able to capture this ache more convincingly in the 2000s than the voice of Leslie Feist. On her second album, The Reminder, the Canadian songstress uses those soft, expressive pipes to drive home a clutch of pop-folk songs that are as delicate as can be. Whether it’s the sharp ache of regret, the pleasurable ache of a new romance or the dull ache of a relationship’s demise, Feist makes listeners feel it, thanks to a markedly un-showoffy delivery and an eclectic mix of arrangements. There are the joyful glockenspiel plinks of “I Feel It All,” the serpentine piano of “My Moon My Man,” the mournful cello of “Limit To Your Love.” As a result, what sounds like a downer of an album on paper is a multi-faceted treatise on love that rivals Joni Mitchell’s Blue.