No one in hip-hop has ever been penalized for talking too much about himself. Proto-MCs in 70s dance clubs were bragging about their rap skills before anyone was even sure what made for good rapping, and from those roots sprang the most explicitly autobiographical pop music in history. You don’t need to read the book or watch the movie to learn about Biggie’s teenage crack-slinging career, Jay-Z’s childhood in the Marcy projects, or the forensic details of 50 Cent’s shooting.

And you can get a good feel for Kanye West’s backstory in maybe three songs from his first album, if you pick them right: raised middle-class in Chicago, he bailed on college and the bourgeois dream to pursue music, overcoming a shortage of street cred to rise to the top of the rap game. Lacking a gangsta’s gritty past and a studio gangsta’s willingness to invent one, he ran out of autobiography pretty quickly–he’s only just turned 30–and so began channeling his desire to write about himself into lyrics focusing on his own genius and the struggles success has brought him. The sort of cocky MCs who obsess about their position on the totem pole rarely seem capable of self-regard more sophisticated than imagining themselves martyrs–they’re keeping it so real that people want to take them down, the fantasy usually goes–but Kanye dissects himself with a clear eye, exploring his own faults more thoroughly than any mainstream rapper before him. Even more remarkably, he does it without resorting to the cliche of the repentant thug or the customary spasms of self-doubt brought on by a fallen homie.

If you just skim the titles on Graduation, which comes out September 11 on Kanye’s own GOOD Music label, you might figure he’s taking a victory lap. “Champion,” “Stronger,” “The Glory,” “Good Life”–not to mention “Drunk & Hot Girls”–they all sound triumphant. But on Graduation he’s at his most vulnerable yet–“Stronger,” for instance, is mostly about Kanye waiting around for a girl to decide she’s into him. The same inability to censor himself that has resulted in his notorious public displays of egotism–like storming the mike at MTV’s European awards show last year to bitch about losing–can also result in disarmingly direct confessions. He’s convinced of his own greatness but direly in need of validation, and even his most self-aggrandizing lyrics are undercut by admissions of weakness (though never self-doubt). Of course, a lot of his confessions are direct consequences of his egotism–he’s his own spin doctor, on each record acknowledging but not quite apologizing for the embarrassing outbursts since his previous release. But Kanye’s also willing to go deeper, into some therapy-level issues.

The most obvious example on Graduation is the closing track, “Big Brother,” nearly five minutes of real talk about his complicated relationship with Jay-Z. Jay was largely responsible for Kanye’s rise as both a producer and a rapper, serving not only as a mentor but as something of an idol. “Have you ever walked in the shadow of a giant?” Kanye asks. It’s intimidating as hell, he admits, but worth it if you can get the giant to give you a nod. “I played my little songs in that old back room,” he raps, recalling the beginning of their collaboration. “He’d bob his head and say, ‘Damn, oh that’s you?'” From there it’s stacks of cash, a crib for his mom, and partying in the club till he blacks out–Kanye basks not only in Jay’s reflected glory but in his approval as well. Mainstream hip-hop is so rife with homosexual panic that even acknowledging the emotional component of a friendship with a living man is seen as suspect–odes to dead men are still OK, as is praising somebody strictly for his business acumen–so it’s truly stunning to hear Kanye cop to the depth of his bond with Jay-Z.

“Big Brother” may be the most intense song about how deeply friendship can affect a man that I’ve ever heard, and it peaks when Kanye details what he sees as snubs from Jay: “Big Brother got a show up in Madison Square / And I’m like, ‘Yeah, yeah, we gon’ be there,’ but / Not only did I not get a chance to spit it / Carlene told me I could buy two tickets.” Kanye’s complaints may seem petty–he’s basically hurt that Jay-Z didn’t recognize him as a genius right from the start–but he nonetheless makes it obvious that his desire to equal Jay’s success and earn his respect was a big part of his motivation for coming out from behind the boards to take a shot at superstardom.

If The College Dropout asked, “Can a Polo-wearing son of intellectuals compete against gun talk and coke-dealer verite?” then Graduation answers, “Obviously he can, but he has to work extra hard to do it.” Kanye’s stepped up his game and made himself some of the best beats in the past ten years of hip-hop. He makes it hard to argue when he calls himself a genius.

Not much on Kanye’s new record sounds like anything else on the radio right now. Though the quavering minor-key synths that form the backbone of the ominously catchy “Can’t Tell Me Nothing” bear some similarity to Timbaland’s work with Justin Timberlake, there’s no obvious connection between any current commercial music and the corrosive funk of “Barry Bonds,” the 70s pop of “Homecoming” (with Chris Martin of Coldplay), or the Steely Dan samples of “Champion.” Kanye is also coming into his own as a songwriter, relying less on old-school beat-and-one-sample combos and more on layered arrangements that camouflage his borrowings: the stomping synth-soul tracks “I Wonder” and “Flashing Lights” are prime examples. This new subtlety reminds me of Portishead–he shows how samples can be used to expand his music’s vocabulary. It says a lot that he can lift huge pieces of Daft Punk’s “Harder, Better, Faster, Stronger”–possibly the best dance song of the 21st century–and somehow improve on the original.

His choice of Daft Punk also says a lot about the latest challenge Kanye has set for himself. He’s proved people will accept a rapper in preppy gear–but will they accept a rapper who acts like a white hipster? Lately that’s the crowd he’s been drawing inspiration from. He’s enlisted Peter Bjorn and John as his backing band and name-dropped TV on the Radio in interviews, and when he took the stage at the House of Blues two weeks ago–at a benefit for the Kanye West Foundation’s Loop Dreams program, intended to help schoolteachers reach potential dropouts by incorporating hip-hop into their curricula–he was wearing a slim-fit cardigan.

Obviously Kanye isn’t satisfied simply being famous. He wants to be famous on his own terms. At the House of Blues, after delaying the show long enough for the crowd to start booing, he took the stage to the massive beat of “I Wonder,” striding out in front of a 12-piece orchestra (complete with harp) like Axl Rose doing “November Rain” at the VMAs in 1992. He got through the first verse–but stopped the show and dropped the curtain before the second, making us wait another five minutes or so before resuming what turned out to be a killer set. I thought about the hissy fit he threw last year at Lollapalooza, when he decided the engineer was making him sound shitty in front of his hometown. He’s willing to tell us pretty much everything about himself, but the one thing he won’t do is let us see him look bad.

For more on music, see our blogs Crickets and Post No Bills at chicagoreader.com.

Art accompanying story in printed newspaper (not available in this archive): At the House of Blues, August 24 photo by Jim Waisman.