Though by no means perfect, Kanye West's debut album, The College Dropout, changed rap and pop music in so many and such fundamental ways that we're still seeing its effects play out almost six years later. Lyrically it was at once self-deprecating and self-mythologizing, club- and radio-ready yet full of introspection and doubt, often all in the same verse. Rapping over his own beats, West's admittedly inconsistent flow and lyricism created some moments of true beauty and insight. And those instrumentals—which attentive listeners had had their ears tuned to ever since hearing West's dramatic organ and piano arrangement on the title track from Beanie Sigel's 2000 album The Truth—were better, catchier, more moving, creative and sophisticated than anything else on the charts. The rap music that had been dominating the pop world for the last eight years suddenly looked just as staid and conventional as it had let itself become. Perhaps most importantly, West offered an alternative to gangsta rap right when it was most badly needed, and in the process set the stage for hip-hop culture's next evolution.

From the first single, there was no denying that he was refreshingly different, alternately prone to earnest admissions of uncertainty and insecurity, and the kind of boastful over-compensations that he's since become notorious for. Compare "Through the Wire" to other debut rap singles of equivalent cultural significance—Eminem's "My Name Is," Biggie's "Juicy," Ice Cube's "Who's the Mack," Eric B. & Rakim's "Eric B. Is President"—and it stands out as possibly the most complex, confessional and heartfelt introduction to the world any rapper has created. West talks over a tweaked Chaka Khan sample through the choruses, then sets the stage for his lyrics with sudden flurries of drums. On the first verse he addresses his new audience like we already know him, talking obliquely about an accident, his mother, his hospital diet and Biggie.

[Listen to "Through the Wire": ]

As if suddenly coming to, he regroups and opens the second verse with what basically amounts to his thesis for the ensuing trio of college-themed records: "What if somebody from the Chi that was ill got a deal/on the hottest rap label around/but he wasn't talking bout coke and birds it was more like spoken word/except he's really puttin' it down." Beginning urgently and evolving into a teasing drawl where "down" gets stretched out into "dowwww...", it's the kind of thoughtful and carefully executed song that became more scarce on West's subsequent records, probably because he hasn't had time to sit still since getting out of that hospital. Of course, using the car accident that left him rapping "through the wire" as his origin myth was just more proof that West was something else. Biggie talked about dealing crack, Tupac concealed his ballet school and poetry-writing days under swaths of gangsta rhetoric, 50 Cent got shot, Eminem got really high, and Kanye West got his jaw broken in a car accident. But he never sounds worried about how this unglamorous, confessional style might sit with the traditional rap fan base, most of whom were already on board for the phenomenal beats anyways. West courted crossover audiences unabashedly from the get-go, which became even clearer on College Dropout's second single.

With "Slow Jamz" [below], West proved he could work with a formula as well as any other producer or rapper in pop music. More than just the token slow jam of its title, the track, which is also featured on Twista's album Badunkadunk and includes a tongue-in-cheek introduction and chorus by Jamie Foxx, pokes fun at its delicious, syrupy sweetness, just as it enshrines itself among R&B royalty, name-dropping everyone from Smokey Robinson, Marvin Gaye and Gladys Knight, to Sly and the Family Stone and Luther Vandross (whose voice the song samples). Though Twista's trademark speed-rapping easily overshadows West's clumsy lyrics ("She got a light-skinned friend look like Michael Jackson/got a dark-skinned friend look like Michael Jackson"), the fact that both Chicagoans can rap in their spectacularly disparate cadences over the same beat is a testament to the producer's terrific craft.

If he seemed to be working with conventional song types on those two first singles the next two, released after the album dropped and West's superstardom began to take shape, flew in the face of tradition. "All Falls Down" is an uncharacteristically sparse acoustic affair, with a melancholic Syleena Johnson hook and deceptively casual verses from West. In the first he does an exceptionally perceptive and vivid version of the "fallen woman" narrative that figures on so many rap records (perhaps most memorably on Tupac's "Brenda's Got a Baby"), which he follows up by taking an equally frank look at himself and segues into what, at the time, was the most articulate and intelligent analysis of contemporary African American identity we'd heard in years. To this date the last verse of "All Falls Down" is West's best writing:

We buy our way out of jail, but we can't buy freedom/we'll buy a lot of clothes when we don't really need 'em/things we buy to cover up what's inside/'cause they make us hate ourselves and love they wealth/... but I ain't even gon' act holier than thou/'cause fuck it, I went to Jacob with 25 thou'/before I had a house and I'd do it again/I wanna be on 106 and Park pushing a Benz/I wanna act ballerific like it's all terrific/I got a couple past due bills, I won't get specific.

[Listen to "All Falls Down": ]

Part of what makes this song so exceptional and, in retrospect, uncharacteristic, is that you could easily miss its brilliance if you weren't listening closely. Nowadays West makes sure the whole world is listening even as he prepares to say phenomenally dumb things.

Nearly as smart but a million times more attention-grabbingly epic, "Jesus Walks" gave a better sense of where West's career was headed. Equal parts military drill and gospel devotional, with driving strings, vocal snippets, and a melancholic Curtis Mayfield sample auto-tuned into a tragic, wind instrument-like wail, it's one of the few times West has carried a song where the lyrics and production were impossible to ignore without a guest. On the stand-out second verse, as he builds to the haunting crescendo, he simultaneously sets himself up as hip-hop culture's martyr and savior: "I ain't here to argue about his facial features/or here to convert atheists into believers/I'm just trying to say the way school need teachers/the way Kathie Lee needed Regis that's the way I need Jesus/so here go my single, dog radio needs this." The track's soulful, dramatic grandeur was a heightened version of College Dropout's dominant aesthetic.

[Listen to "Jesus Walks": ]

Much of the rest of the record relied on a set of spectacular guest appearances, which sometimes made it sound almost more like a producer's compilation than a rapper's album. This wasn't necessarily a bad thing; as his last album can attest, a whole record of Kanye West doesn't really work. For a trio of songs that seemed designed to appease the rap fans who maybe didn't want to hear about West's crushing self-consciousness issues, some of his most respected peers lent some street cred to an artist who otherwise didn't seem terribly concerned with asserting his battle rap bonafides. "Get 'Em High" with Common and Talib Kweli, and "Two Words" with Freeway and Mos Def are spectacular, gritty street anthems, and West does admirably stepping into the gauntlet. He plays sidekick to Jay-Z on "Never Let Me Down," another grandiose, moody, gloomy example of the style of soul-tinged hip-hop that West reinvigorated.

To be sure, The College Dropout made a few missteps, most notably an excessive number of skits, an overlong autobiographical outro, and a disappointing Ludacris collaboration on "Breathe In, Breathe Out." But even the brazenly empty-headed "New Workout Plan" amounted to more than the sum of its very modest parts. More importantly, the album revealed a nearly self-sustaining and undeniably original creative force in rap with an indiscriminate hunger for folding any and every musical style into his Pro Tools box—at the time much was made of his use of violinist Miri Ben-Ari throughout the record as being an indicator of rap's newfound musical maturity. Though the mutation wouldn't happen until the "college" trilogy was completed with Late Registration (2005) and Graduation (2007), West was starting to retrain our ears for a new kind of rap music and, ultimately, a more adventurous style of pop. In doing so he brought hip-hop and the mainstream into a more collaborative relationship than ever before, and started the long overdue process of moving rap out of its gangsta mode and into a more self-reflexive, comic direction, both in terms of music and in the more general realm of style. More so than any of West's subsequent albums, or any other rap record this decade, it's hard to underestimate how profoundly The College Dropout affected the evolution of pop music.