Lil Wayne Is Out of Prison. Now What?

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I'mma live my life like there's no tonight
I might go tonight
So momma pray, don't cry

–Lil Wayne "2 Pac Dedication"

Lil Wayne is free, and he is beloved. For the past eight months, as he served out a prison sentence for attempted gun possession, Wayne has maintained contact with the public through his website, In post after post, he thanks those who support him for their kind words and prayers. The comments section of the website is littered with adoration for the hip-hop hero—positive vibes that are expected to transfer directly to album sales for his latest project, Tha Carter IV, now set for release on December 14th.

It is virtually certain that the album will be a financial (if not musical) success. Wayne's reign, slightly dampened by imprisonment, shows no visible signs of weakness. But the incarceration reveals cracks in the foundation of his empire, and there is cause for concern about Weezy's future. In examining our love affair with the biggest Lil' man in the industry, the reasons for his appeal are not hard to discern. But these reasons pose urgent questions about what we can reasonably hope for the remainder of his career.

People love Weezy's music, and he makes plenty of it. "Bling Bling" and "Lollipop" will bang in clubs and college dorm rooms for generations to come. His album Tha Carter III garnered four Grammy Awards, and a steady trickle of mixtapes, including the "Dedication" and "Da Drought" series, keeps fans buzzing in the time between official releases. Though the content of his raps is not the stuff of revolution, Wayne's flow and capacity for wordplay are, at times, dazzling.

Weezy-love extends beyond the stage and recording booth, and anyone who has watched Wayne's television appearances can attest to his thoughtfulness and charisma. Whether cracking jokes on The View, performing on BET's Spring Bling, or trading opinions with sports writers on ESPN, when Weezy seems contented or engaged, the feeling spreads to his audience.

But we are also fascinated by Wayne's capacity to endure pain and negotiate his own self-destruction. His body bears his suffering, as his face, neck, and torso are covered in ominous tattoos. His voice, summoned from smoke-filled lungs during sleepless nights, often scratches and strains on the track, imbuing his delivery with urgency and desperation. He is a survivor. Poverty in New Orleans, the gauntlet of the music industry, and prison have all taken their toll, but not slowed Wayne's roll.

So what's next for Wayne now that he's a free man? There are two proven models for extending hip-hop careers. One is the Ice Cube, rapper-turned-actor-producer model, where there is a clear shift from music to film, but the artist remains a performer. The other is the entrepreneurial approach, where artistic performances decline in frequency, but connections to the music industry remain. In these cases, the artist-turned-executive wields influence from behind the scenes, building record labels and extending his brand to clothing, liquor, and other ventures. Jay-Z's recent appearance on the cover of Forbes magazine with Warren Buffet solidifies his stature as the standard-bearer for this tradition. The establishment of Wayne's Young Money Records imprint seems like a step in the entrepreneurial direction.

Prison can derail this journey, however. Tupac Shakur seemed destined for a lucrative film career until he was sent away. Shakur emerged from jail somewhat desperate and indebted to Suge Knight and Death Row Records, which cast him in a dangerous role and exposed him to new social networks comprised of exceedingly impolite company. On a less tragic note, rapper/actor T.I.'s career was put on hold this October, after he violated the terms of his probation and was sent back to jail for 11 months.

The reasons people go to jail are not always just, but the experience of incarceration should leave an imprint; it is demeaning and miserable. In most cases, the effects are disastrous. Prison provides no rehabilitative function, the experience is traumatic, and the prisoner exits in worse social and financial condition than when he entered. However, for the privileged few who have the support systems and incentives in place to avoid recidivism, the experience need not be repeated.

The danger in Wayne's case is the possibility that he emerges financially, socially, and emotionally unscathed (all good), but sees no reason to change anything (not so good). The record sells, the love keeps flowing, and the prison bid becomes a footnote in his mind. He buys into the notion that he is untouchable, and we do too, despite the fact that he remains on three years probation, thanks to a separate drug conviction. He continues to live his life "like there's no tonight," and then, night falls. And the music stops.

Presented by

Michael P. Jeffries is an assistant professor of American Studies at Wellesley College and author of  Paint the White House Black: Barack Obama and the Meaning of Race in America.

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