Lil Wayne Goes to Jail

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

Lil Wayne
Peter Yang
Lil Wayne on the cover of Rolling Stone.
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'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."

As his productivity increased, Wayne's tattoos multiplied, his outfits got more flamboyant and his reputation for drug intake grew. Wayne has confessed addiction to promethazine-codeine syrup, or "drank" — the cough-medicine-based drink that allegedly killed Houston rapper Pimp C in 2007. For the 2009 documentary The Carter, a camera crew followed Wayne around, capturing his remarkable talent but not shying away from showing the Styrofoam cup of syrup that seemed to always be in his hand, or its effects on Wayne's personality. In one scene, Wayne intones, "I am Frankenstein," and glowers woozily at the camera. Another scene has Bryant haltingly confessing, "I was ready to walk away. I can't look at him in that state." Later, Wayne tried and failed to stop the film's release; Bryant said that Wayne didn't get the approval he was promised, and that they "didn't like that angle." But when I bring up the syrup issue, Wayne brushes it away.

"I haven't fucked with that in a long time," he says of drank, saying that he quit cold turkey on May 9th, without withdrawal symptoms. When I ask about other drugs, he says, "I smoke weed all day." When I ask him if he's an addict, he says, "I'm a very successful addict. And a very smart one. And a very charismatic one. And one that just won four Grammys, and one that sold a million records in a week. One that still appears on everybody's songs, one that still sounds better than any rapper rapping. One that has four kids and is the greatest father ever to the kids." He laughs. "What am I addicted to, being great?"

Wayne pleaded guilty in October, two years after he was arrested for weapons possession following a concert he gave at New York's Beacon Theatre. According to reports, NYPD officers smelled pot smoke coming from Wayne's tour bus, pulled it over, then boarded it and found a .40-caliber handgun. Wayne was charged with gun possession and, after fighting it for two years, reached a plea agreement in October on charges of second-degree attempted criminal possession of a weapon.

Lil Wayne will almost certainly do his 12 months apart from the general population at Rikers Island, in a dormitory-style unit like the one that once housed football player Plaxico Burress (currently in prison on a weapons sentence) and other inmates the corrections department classifies as too vulnerable for the general population. But attorney Benjamin Brafman, who represents Burress, suggests Wayne's biggest challenge may be the time itself. "For many people who are Type-A personalities, there's a cooling-down period," Brafman says. "Where you don't have liquor, you don't use drugs, you don't stay up until 4:00 in the morning."

The person most responsible for keeping Wayne's career going for the next year is Bryant, a slim, preppy-styled 30-year-old who befriended Wayne when he was 15 and Wayne was 12, pulling him away from his violent background into school groups like McMain High School's marching band and looking after him ever since.

"You can't deny that in this industry, if you sit out six months you'll kill your career," says Bryant. To prevent this, Cash Money is going into overdrive to promote Wayne's Rebirth and the new album from Wayne's crew Young Money, recording a flurry of videos — for both album tracks and loose songs with Young Jeezy, Flo Rida and others — to be released while Wayne is in jail. Wayne is also performing with Eminem at the Grammys, his last major appearance before he goes in. The plan is to release the biggest bullet in Cash Money's chamber, Tha Carter IV — the follow-up to the million-a-week-selling Carter III — shortly after he gets out, hopefully in eight to 10 months for good behavior. The label Wayne largely funds will move its operation from its Miami base to New York for the duration of the sentence. Bryant is exploring jailhouse Twitter accounts, TV shows, clothing lines, creative commercial tie-ins, endorsements and any other means possible to hang on to Wayne's audience. "So his fans feel like they can touch him and reach him and see him and feel his music, so they won't miss him at all," says Bryant.

Half an hour outside Atlanta, Lil Wayne stands before the mixing board of Tree Sound Studios at 3 a.m., dressed for battle: super-low-slung black Levi's cinched at the upper thigh by a belt, and a black-and-white-checked bandana hanging out of the right back pocket, a black pinstripe cowl-neck jacket with the collar up, a white Polo tee and a purple college baseball hat over his flowing braids. A banging, Rick Rubin-style mid-Eighties hip-hop beat by Miami producer StreetRunner — which may or may not make it on to Tha Carter IV — booms from the monitors. Wayne breaks himself off a piece of Gummy Zone Sour Fries, and, eyes closed and head bowed, listens.

Wayne's engineer Mike Cahadia sits behind the board, peering at an open MacBook Pro. The dreadlocked 26-year-old has traveled in Wayne's inner circle for six months, bringing four or five beats to sessions daily, many from local Miami producers; he says Wayne has been favoring vintage, hard Beastie Boys-ish stuff lately. "He's the hardest-working artist, hands down," says Cahadia. "There's no comparison." Wayne's been recording guest spots for Young Money artists Gudda and Jae Millz, and tracks for Tha Carter IV.

The album Cash Money staffers internally designate "C4" (because it'll be the bomb) lives on a 500GB LaCie hard drive somewhere close to Wayne or Bryant, like the nuclear-launch codes that travel with the president, with a backup somewhere else in the Western Hemisphere. It will inevitably leak before it's released; the goal is to make sure it leaks days before it hits stores, rather than weeks or months. ("Two weeks is acceptable," says Bryant.) Nobody in Wayne's camp will play us any of the music, although Bryant describes its songs as having a tougher, faster edge. It's more or less done, but Wayne will probably keep adding to it until the last minute.

At around 4:45 a.m., the speakers are blasting a loose-limbed beat centered around the scratched rock-guitar blare from LL Cool J's "Rock the Bells." Shoulders rounded, Wayne grooves to it, ball-cap brim nodding. He plays air drums on the kickoff and then starts bouncing like a prizefighter. He's trying to get pumped, but nothing is coming together. Not a word has been committed to tape.

Forty-five minutes later, I find him outside at a pool table slamming balls against the sides. I ask if he wants to talk. "Nah!" he says. "I'm done talking!" He slams a ball hard and storms past me. As he does, I get what E.I. called the "Wayne look": a cold, hollow-eyed stare that says you're nothing but a clog in his flow. "If he don't like something, he's going to let you know," says E.I. "Whatever's wrong better be right in the next couple seconds." A minute later, Wayne emerges with coat and Vuitton bag, heading for the exit. I figure he is going to sleep and fight another day. The next day, I find out he just moved to the tour-bus studio and kept going, for hours.

In Miami, with the Rikers clock at T-minus 20 days and counting, Team Wayne has turned the concrete set of Propmasters Studios into a national epicenter of nonstop music-video production. For the past two weeks, Wayne has been performing almost all of his verses before green screens so that Cash Money can store them like high-grade frozen sperm for later use. Today the project is "Roger That," a song by busty, trash-talking Wayne protégée Nicki Minaj; last night's shoot was the teen-friendly devotion song "Girl I Got You," by post-pubescent duo Lil Twist and Lil Chuckee. "Songs are coming in barely mixed," says director David Russo. "Just in case there's something with Wayne on it they can use. You wake up one day and look at your e-mail inbox and there's another MP3 and the message 'We want to shoot this tomorrow.'"

In the dark main bedroom of a tour bus sits the imposing, soft-spoken Cash Money chief Bryan "Baby" Williams, looking prison-yard hard with a bald, tattooed head, a boxer's maroon hoodie and sweatpants, 30-carat pinky rings, giant diamond earrings and a platinum grille that glints in the ultraviolet light. If Cortez Bryant represents Wayne's diversified new-media career, Williams represents New Orleans' dirty soul. Twelve years ago, before a shoot, Williams read the plan for a Cash Money video and saw a scene calling for a trunkful of money. Unaware that videos use prop bills, he arrived at the shoot with $750,000 cash. Even after he learned better, Baby insisted on the real thing. "It smells different, it feels different," Wayne's video producer, Jeff Panzer, explains. "When it's real, it's real."

"Wayne is my son," says Williams. Williams has done time, has family doing 25-year bids, plans to visit Wayne every week. "I've been with him forever," he says. "It will be the first time in my life I'll not be reachable to him. We work together, we're on the road together. We're always together. I try not to even think about it." His eyes watering, he says it feels like he's the one going inside. "I'm losing something in my soul, in my heart, in my life."

At 7:30, the call comes over the walkie-talkie: Wayne has left his tour bus in the parking lot and is moving toward the set — "Wayne walking." Crew members get in place, phone conversations end. "Twenty feet on Wayne. Ten feet on Wayne." Over a speaker, the bad, swaggering, lower-brass riff of "Roger That" comes in, louder than before. "Five feet on Wayne." And — "Wayne time" — Wayne enters, spewing blunt smoke, the red collar on his Neighborhood khaki jacket up, braids flowing behind his ears.

Rapping along with his verse's syncopated banzai, "I'm comin' in!" Wayne literally jumps into the verse: feet landing on "Fresh off the jet," up on toes for "sharper than Gillette," and bouncing back down on "the blood still wet," ambling through the lyrics wearing oversize gangsta-nerd glasses and a foot-wide diamond smile. After "cut," he walks to the side and takes a call. The track starts again and he comes back and does another, totally different take, lip-syncing and profiling with the seemingly effortless magnetism of someone who began doing videos at 14. He kills it five more times — three setups, three takes each, one group shot — and wraps at 8:10. Thirty minutes, total. "That's a world record," says Panzer.

Before Wayne splits, he pauses for a photo with members of the Cash Money and Young Money family, whose young members project a remarkably wholesome vibe considering the fact that Nicki Minaj declared herself "tight like a dick in a butt" in a rhyme earlier today. She, Tyga, Lil Twist and Lil Chuckee all look like third-generation Corleones compared to bald, muscled, sunglasses-shielded Birdman, who comes out and gets into a big hug. Wayne climbs in, flashes another grin and is out.

I have my last conversation with Wayne the way most people will for a while: on the phone. His voice is a deep croak; he sounds like he's been up for weeks. His final days before jail will be a blur: Amid all the videos, he'll watch the Cavs play the Lakers in Cleveland, then Nuggets-Hornets in Denver, spend as much time with his kids as possible, make a farewell appearance at a Miami concert on February 6th, and on the 7th attend an afterparty for the Super Bowl.

I ask what's the strangest thing about the past two months. "You know what's strange?" he says. "It's strange getting older, that's what's strange." Apparently, jail time doesn't compare. A day ago he watched an all-Wayne fest on the TV station Fuse, got lost in those memories. Like the one 11 years ago of a skinny, do-ragged 16-year-old scrub jumping up and down in front of a camera crew next to a stretch Hummer, waving two fistfuls of cash and lip-syncing verses to "Bling Bling'" — a song named after a word he says he coined, a word that would define an American era. He saw people from that shoot yesterday, only older. "That's what's crazy," he says. "It's like a movie to me."

Is he the movie's hero? "Um, I don't believe in heroes," he says. Wayne has FEAR tattooed on one eyelid and GOD on the other and says he believes "everyone should fear God. Fear not living Godly." I ask how he knows when he isn't — does he look for signs in his life? "I don't look for signs," he says. "But when things happen, I say, 'OK, something must be right.' Or 'OK, something must be wrong.'"

What does he say now, about this? "I look at things as everything is meant to be," he says. "I know it's an experience that I need to have if God's putting me through it. So I don't look at it as wrong, I just . . . I damn sure don't look at it as right, that's all."

Things will change, he says. He'll go back to writing lyrics for a while. But he won't be stopping: "I'll have an iPod, and I'll make sure they keep sending me beats. I'll be still rapping in there, have a gang of raps ready when I come back home.

"You can do that," he says. "You can have music in there. You can have music, period, bro."

This story is from the February 18th, 2010 issue of Rolling Stone.

From The Archives Issue 1098: February 18, 2010
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