Lil Wayne Goes to Jail

Up all night with hip-hop's unstoppable machine as he prepares to spend the next year behind bars

February 18, 2010
Lil Wayne
Lil Wayne on the cover of Rolling Stone.
Peter Yang

'I don't like to stop," says Lil Wayne. "I believe you stop when you die." The biggest rapper in the world stands 23 floors above Atlanta and five feet six in black Chuck Taylors, his wifebeater tee baring a torso as ink-covered as the pages of a doodler's notebook. It's 8:30 p.m., two days after Christmas, and he will be up for the next 11 hours — monitoring four football games, smoking blunts, six or seven of them, sending 40-odd texts (including condolences to his mom for today's loss by the New Orleans Saints), making calls and auditioning 600-odd bars of potential beats over six hours in a recording studio.

Dwayne Carter, 27, has been on this schedule for close to a decade. But on February 9th, one week after he drops his rock-oriented seventh official studio album, Rebirth, he begins a 12-month sentence for gun possession, stemming from a 2007 charge. He's known plenty of people from his old neighborhood who have gone to jail, but he hasn't asked them for any advice on how to prepare. "This is not something you get no advice on," he says. "This is Lil Wayne going to jail. Nobody I can talk to can tell me what that's like. I just say I'm looking forward to it."

Tonight, the rapper wears his long dreads tied back, along with bookish, black-framed glasses and Polo pajama pants. A small diamond cross hangs on a thin chain around his neck. "It's the only jewelry I wear every day," Wayne says in a deep rasp, then flashes a sleepy, diamond-encrusted smile. On a glass table before him are his iPhone, T-Mobile Sidekick, a box of Swisher Sweets cigars, a bag of Sour Patch candies, a bottle of iced tea and a roll of about three grand worth of hundreds — "just in case I need to send someone to the store."

Lil Wayne: A History in Photos

An enormous amount of man-hours goes into keeping Wayne happy and creative — to keep his torrential rhyme flow, which earns around $150,000 per guest appearance, coming. He's never far from a recording studio or a portable recording setup (even if it's just a professional mike and a laptop with GarageBand). Wayne's personal chef, Noel, stands at parade rest in a double-breasted black uniform and apron, ready to prepare steak or chicken in minutes. Somewhere within text-message summons awaits Wayne's personal driver, Mr. G., who wears a slate-gray chauffeur uniform, complete with cap. "It ain't no party," says E.I., Wayne's road manager, who lives with a T-Mobile dedicated to one caller. "You don't get no sleep. There ain't no such thing as 'off.'" E.I.'s main daily goal, he says, is to be awake before Lil Wayne. "Even if it's just 10 minutes."

Timeline: The Criminal History of Lil Wayne

A laptop displays Wayne's fantasy-football team, the South Beach Sloths (named while watching Animal Planet); the flat- screen TV in this room has the Eagles-Broncos game; the TV in the other room has Cowboys vs. Redskins. Wayne, an occasional blogger and on-air commentator for ESPN (whose logo he has tattooed on his leg), hates to miss a second of SportsCenter. A young woman in a sweatsuit quickly walks by carrying an infant in a car seat. "That was Neal," says Wayne, "the newest" — thus distinguishing the three-week-old son with singer Nivea Hamilton from the 15-week-old he just had with actress Lauren London — his third and fourth children, after Raginae, 12, and Dwayne III, 1, and more proof how little he fears flooding the market with material.

Two days ago in Miami, where he also has a house, Wayne celebrated "the greatest Christmas I ever had," he says, sparking a blunt. "We had a big-ass tree. It was 12 feet high. We had stockings — I filled 'em with iPhones and Flip cameras. Raginae had a blast, Dwayne had a blast." Wayne's high school sweetheart Toya, with whom he had Raginae when he was 15, gave him his favorite gift: a pressure-point headband designed to treat migraines. "I've had them ever since I was 12, since my accident," says Wayne, alluding to a mishap in 1994 when he accidentally shot himself in the chest with a 9mm pistol belonging to his mom's boyfriend, missing his heart by a centimeter.

Wayne feels he survived for a reason. "We're here to live," he says, hunched forward on the sofa. "We're here to do, we're here to be. And this here, this is what I'm doing, so I'm gonna do it. Because when it's over, man, it's over." He exhales smoke. "I didn't know I was gonna be going to jail. This happened at the height of my career! Nobody knows the future." For now, his only certainty is that on February 8th, Lil Wayne will leave the hermetically sealed perpetual-motion machine he has helmed for six years, board a jet to New York, take a car to Rikers Island and do something he has compulsively avoided doing for his entire adult life: stop.

The evolution of Lil Wayne — from New Orleans kiddie gangsta into dreadlocked, multiplatformed pop phenomenon — started early and quickly built momentum. Wayne was signed by Cash Money Records at age 15 and joined the Hot Boys, the flagship group of an almost Motown-like factory devoted to synthy tracks booming from SUVs about cars and jewelry. As Wayne grew more experienced, he spent endless hours in a local studio, taking chances and developing into a self-described Martian from Planet Weezy. "I went from being a rookie — just pure motivation — to noticing that 'OK, I'm becoming different.' Once I got a whiff of that, it made me keep going." Wayne stopped writing down lyrics — he says it freed him up to be more expressive in the studio. "I started thinking, 'You are kind of crazy, in a great way.'"

At 21, after middling solo efforts, he effectively launched the Lil Wayne brand with 2004's Tha Carter, whose cover showcased his now-signature dreadlocks, and solidified it with 2005's hit Tha Carter II, which debuted a radical new style of croaky, nonlinear rapping and expanded his sound with a range of producers. A remarkable two-year period followed, in which Lil Wayne released new material almost constantly — and against his label's wishes — on a slew of hype-building mixtapes and guest appearances. It culminated with Tha Carter III, the last rap album to sell a million copies in a week.

"The label said, 'Oh, no, no, stop,'" says Wayne's manager, Cortez Bryant. "But between Carter II and Carter III, his status was actually growing because of all the things he was doing outside of studio albums. He said, 'Trust me — I've got this, I've got a plan in my head.'

"A normal person probably can't deliver as much music as he delivers, because people get tired of the same thing," adds Bryant. "When Wayne was coming out with all those songs and all those mixtapes, he was giving you different flows, different patterns. He was pushing the envelope. Normal people can't do that."

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