The Last Hustle

You can now walk a mile in Jay-Z's shoes. As of April 2003, two different S. Carter by Reebok models went on sale for $99.99. So not only can you drink the Armadale vodka he hawks at the club he owns and dress your entire family in outfits from his Rocawear clothing line, you can buy footwear with his signature on the back. But after listening to Jay-Z's most revealing record ever, The Black Album, you still won't understand how it feels to inhabit his pristine 10-and-a-halfs.

Jay-Z wears each pair a maximum of twice. "I've noticed that when people have had money for a long time, they never talk about it, they don't show it," he told me during an interview at Baseline Studios in New York—wearing jeans, a jacket, and S. Carters, of course. "But I'm that same kid from that neighborhood with that insecurity, who feels like if I get the car I'll feel better about myself because it's been too long feeling bad about myself. Lyor Cohen wears New Balances 80 times. If I wear Reeboks two times, I gotta get rid of 'em." He paused and smiled. "I'll get there one day." After saying "If I wear," Jay-Z began an almost imperceptible "N" sound, but stopped himself before completing the word "Nikes," replacing that financially inconvenient stutter with "Reeboks." Jay-Z has the first sneaker deal for a non-sports star to protect.

He's also got a reputation to look after. Jay-Z is a confidence artist, and he's gotten rich by not making it personal—teaching the swagger but seldom betraying the emotional limp that caused it. Now, after nine studio albums and undisclosed millions in revenue, Jay-Z says he's retiring from rap. He claims that he's no longer inspired by the hip-hop world, but the content of The Black Album and his contemplative conversational tone suggest that he isn't just bored by what other people are doing—he's bored by the alter ego he's outgrown. The risk-averse rapper calculates, however, that it's the smooth criminal the public has fallen for—the reason he can sell athletic footwear without a jump shot—and he's not about to jeopardize his financial future. Instead, he's doing his best to preserve the myth for posterity.

On a Metro North train the day after The Black Album is released, a young woman carrying a Rocawear bag listens to the album on her headphones. She's mouthing the lyrics already. Jay-Z's recording persona is so compelling because though he's still a caricature—certain features are disproportionately emphasized—he's an elegantly rendered one. Says Kanye West, the producer responsible for some of Jay's most sinuous beats, "Jay-Z can't be a loser. He can't say anything that could come off as uncool. And if he does he has to figure out the coolest way to say it." Somehow, in spite of the disposables he's picked up along the way—shiny shirts, Shaquille O'Neal collaborations, rotating cast of Roc-A-Fella sidekicks, endless product placements—Jay-Z's Teflon nonchalance seems timeless.

"Coming up, I experienced the worst pain a person can experience, period," Jay-Z said. "Your pop is your superman, and when that's taken away from you, you never want to put yourself in that position again." He explained the birth of his cool candidly. "I always grew up [thinking], if you say you don't care about it, then no one can hurt you. People called me jazzy, I was a cool guy for my age, but that's where it stemmed from."

Jay-Z patented his chilly brand of calm on his classic debut, 1996's Reasonable Doubt, which is still his favorite. "It was my first album, so I didn't have a target audience," he said. "I didn't know anything about making music. That was the best album for me because I was just doing what came naturally." Reasonable Doubt is honest not in the sense of soul-baring but in the sense of unselfconscious. "I was just trying to tell a story and keep it in rhyme form so that my friends would be like, 'Wooo,' " he said. Concealed within the album are a wealth of tricky lines you brush past at first. On the hustler reality check "D'Evils," he raps, "You know the demon said it's best to die/And even if Jehovah Witness, bet he'll never testify." "I call that the Easter egg hunt," Jay-Z told me. "With every album I try to do that, but I think that was the one that had the most Easter eggs."