Inside Lil Wayne's Experience In Prison

In the hip-hop genre, there are few stars bigger than Lil Wayne. The New Orleans-born rapper — whose real name is Dwayne Michael Carter Jr., but will also answer to Weezy — has enjoyed an incredibly successful career since the release of his debut album, "Tha Block Is Hot," in 1999. 

Despite all that success — and a reported net worth of $170 million — he's had his brushes with the law. The most notable was a 2007 gun charge that resulted in a year-long prison sentence (eventually reduced to eight months thanks to good behavior). Spending all those months in jail during the height of his booming music career would certainly prove discouraging to anyone. For Lil Wayne, however, it was just another of life's hard knocks that he took in stride. Speaking with Rolling Stone shortly before reporting to prison, he said he was actually looking forward to the experience. "I look at things as 'Everything is meant to be.' I know it's an experience that I need to have if God's putting me through it," he said, as reported by NME. "So I don't look at it as wrong, I just ... I damn sure don't look at it as right, that's all."

He served his time and emerged a free man, enjoying even greater musical success in the wake of his incarceration. For a retrospective rundown of that difficult time in his life, read on for a look inside Lil Wayne's experience in prison. 

Back in July 2007, Lil Wayne had just experienced one of his most triumphant moments when he performed in New York City for the first time ever, headlining a show at Manhattan's Beacon Theater. As MTV reported, Lil Wayne's NYC debut was heavily attended by fellow rappers, along with a significant police presence.

According to a report from Vibe, police officers apprehended Lil Wayne and another man after the show, having spotted them allegedly smoking weed near a tour bus outside the venue. When the cops took the two men into custody and performed a search, they allegedly found a .40-caliber pistol. Lil Wayne was arrested and charged with criminal possession of a weapon. 

As The New York Times reported, Lil Wayne initially entered a plea of not guilty to the charges, for which he faced a maximum sentence of three-and-half years in prison. While prosecutors argued that he'd tried to conceal the weapon, the rapper's lawyer, Stacey Richman, claimed that the gun did not belong to him, was not on his person, and that police had no legal basis to be on the bus in the first place. "He [Lil Wayne] was in the bus in his boxer shorts with a number of other people," Richman told MTV News. "Unless his boxer shorts had a pocket for this gun, I don't understand how he had it on him."

Despite the protestations of his lawyer — who said that the gun belonged to Lil Wayne's manager, Cortez Bryant (who possessed a permit to carry the weapon in Mississippi) — legal wrangling about whether or not DNA evidence on the gun would be admissible in court did not fall in his favor. as The Guardian noted, the rapper's lawyer admitted that evidence was "problematic" to Lil Wayne's case. Instead of going to trial, gears were shifted, and Lil Wayne entered a guilty plea to a lesser charge, "attempted" gun possession in the second degree.

"After ongoing negotiations, [Lil Wayne] opted to take the deal to take responsibility for the situation and I think it speaks of him that he's an individual with a strong constitution who took that responsibility," attorney Stacey Richman told reporters, still insisting the gun was not his. Prosecutors recommended a sentence of one year behind bars.

Lil Wayne's sentencing was delayed — twice. The first delay was due to some dental work that Lil Wayne needed to have done. The second was caused by a fire that broke out in the courthouse. Finally, Lil Wayne appeared in court to face the music. "That's the sentence I'm imposing, one year," Justice Solomon Justice Charles Solomon of the State Supreme Court told the rapper, reported The New York Times. Lil Wayne was placed in handcuffs and escorted out of the courtroom to begin serving his sentence at New York's Rikers Island jail facility.

Lil Wayne arrived at Rikers Island on March 8, 2010, to begin serving his one-year sentence. Just two months later, he'd landed himself in trouble behind bars when a routine search of his cell uncovered the charger for an MP3 player and a set of headphones, which he'd hidden among some trash. "We found the items wrapped in an aluminum potato chip bag, in a garbage can," a prison official told Fox News. Further searching revealed the discovery of an MP3 player, hidden in the cell of another inmate, that matched the charger found in Lil Wayne's cell. Those items may have seemed benign but were considered contraband; both Lil Wayne and the other inmate were charged with possessing contraband, with officials promising repercussions involving some unspecified disciplinary action. 

In retrospect, Lil Wayne may have brought the search upon himself with a revelation he shared in a pre-prison interview with Rolling Stone. "I'll have an iPod, and I'll make sure they keep sending me beats," he bragged.

Lil Wayne later confirmed that he had indeed been busted, just as had been reported. "Yeah, they tried to bang me with that," he said in a phone call from prison to pal DJ Scoob Doo, reported by Vulture. "But it's just music, I can't live without my music, Scoob. You know how it is, man. I needed my music. It's all good, I had to take my little slip up."

Lil Wayne tried to remain productive while serving his prison sentence. Evidence of that can be found in "Gone 'Til November," a collection of musings from the diary he kept while behind bars. Published several months after his release, the book offered insight into his months in the slammer. 

Given that he was confined to a tiny cell with nothing to do, the entries aren't particularly interesting — although they do shed light on the often mundane nature of prison life. "This is the kind of s*** that has become worth writing about: eating Oreos and drinking grape Kool-Aid. Damn!" he wrote in one entry, excerpted by GQ. In another, he demonstrated that his libido remained active behind bars. "And then there's Ms. Burke. Owww! She's so sexy!" he wrote of a female corrections officer. "I mean, she's fine as hell! I'd definitely hit it!"

As he revealed in his author's note, his diary wound up becoming a form of salvation for him that kept his creative juices flowing. "I was just doing something to pass time in there," he wrote, as excerpted by The New Yorker. "It became something to look forward to every night, which is very difficult to do when you're locked up." He elaborated in a post-prison interview with Rolling Out. "You could be so bored in there you do all kind of s*** you ain't think you could do," he said.

In addition to smuggling headphones and writing mundane diary entries, Lil Wayne also reached out to fans directly via a special website that his team at Young Money Entertainment set up. As Rolling Stone reported at the time, the site — WeezyThanksYou.com, which is no longer active — allowed him to respond to his fan letters and messages of support. "During my prison stint, I want my fans to know I love you," he wrote in his first post on the site. "I want all of you to know that I appreciate all the mail I get, and this is my way of saying thank you."

He also shared some insight into how he'd been spending his time, revealing he'd been working out a lot and reading the Bible on a daily basis. As he explained, his faith wasn't something that had been brought about by his incarceration. "Jail didn't make me find God, He's always been there," Wayne wrote. "They can lock me up, but my spirit and my love can never be confined to prison walls." According to Rolling Stone, he intended to update the site at least once a week, and subsequent posts included a special Mother's Day message. 

In addition to his posts, the site also featured a clock that counted down the seconds until he'd be released, along with the mailing address of Rikers Island and an online store selling $29.99 "Free Weezy" t-shirts.

Prior to Lil Wayne entering Rikers Island, a prison guard at the facility spoke with MTV News about what his life would be like inside the joint. Despite his fame, the guard said that the rapper would be treated just like any other prisoner. "He'll be housed with inmates who are classified in his category, and he'll be able to be a regular inmate," the guard explained. "He'll be able to watch television, go into the day room and congregate with people of his classification."

As Lil Wayne recounted in his prison diary, subsequently published as "Gone 'Til November," he did indeed watch television while behind bars, including such shows as "American Idol" and plenty of sports. A particular favorite was apparently a once-popular reality show hosted by the future 45th president of the United States, Donald Trump. "Watched 'Celebrity Apprentice, but couldn't watch it all, had to lock in before it went off," he wrote in one diary entry that was excerpted in GQ. Ever resourceful, Wayne managed to find out which celeb wound up getting eliminated. "I was still able to find out who got fired on the radio," he added. 

As he noted in the diary, there was one show that he simply couldn't tolerate, revealing that Wendy Williams' eponymous show made him flee back to his cell. 

As that Rikers prison guard told MTV News, Lil Wayne was able to receive two visitors each week. One of those visitors, he wrote in his diary, was Sean "Diddy" Combs. Combs' trip to Rikers was particularly eventful, with Lil Wayne's diary entry for that day detailing how everyone in the visiting area appeared to be completely starstruck. "Diddy kept his word and visited me today. It was total chaos!" he wrote, according to an excerpt shared by Revolt, "Every captain in the building was down there! Even the deps and the warden! Everyone just wanted to see him. It was kind of aggravating, but it is what it is."

Combs wasn't the only one of his famous friends to pay a visit to Lil Wayne during his incarceration. "I have to give props where props are due ... big shout-out to Diddy, Chris Paul, and Kanye [West] for coming to see me, especially with their schedules," he wrote, naming some others who dropped by. "I know that they had to go through some extra s***, because you just can't walk in this b**** and say, 'I want to see Dwayne Carter.'"

Other celebs who stopped by Rikers to pay their respects were Birdman, Drake, Nicki Minaj, Tyga, and rapper Cory Gunz, who had been Lil Wayne's protégé prior to his incarceration.

While it may have appeared that Lil Wayne was treated like any other inmate, a fellow prisoner who was incarcerated at Rikers during the same time claimed that wasn't actually the case.

According to a post in the forums on the Lil Wayne HQ website, that former inmate claimed that the rapper actually served his time apart from the prison's general population. "Contrary to what was written in most newspapers, Dwayne 'Lil Wayne' Carter was housed in Protective Custody Cells," the writer of the post alleged. Those particular cells, the person who wrote the post explained, were reserved for those who were at high risk of being abused by other inmates. "This is where the jail would house some Snitches, Homosexuals, Child Molesters, Incarcerated Cops, former Correctional Officers, and occasionally High-Profile Cases," the post noted, with Lil Wayne fitting into the latter category.

The writer further alleged that he was occasionally assigned the job of bringing Lil Wayne his meals, as his status in protective custody didn't permit him to dine in the mess hall. Beyond that, however, Lil Wayne didn't receive any special treatment. "He didn't have any laptop or any other special privileges. The only thing that would separate him from the rest was that he had 'front gate visits' (visits in private). Where all other inmates would see friends and family in a big gymnasium."

While the Rikers guard who spoke with MTV News didn't believe that Lil Wayne would be given a job while serving his time, he wound up getting one anyhow. According to a report in Billboard, an anonymous corrections officer who reportedly observed the rapper's cell revealed that he'd been hired to work on suicide watch — which basically involved observing his fellow prisoners and alerting guards if he had an inkling that any of them might be inclined to harm themselves in any way. 

"He likes the job even though they don't pay him much," Antonia "Toya" Jackson, who shares a child with Lil Wayne, told Us Weekly (via Rolling Stone) of his job looking out for potential prison suicides. "He watches the crazy prisoners and makes sure they don't kill themselves," she explained.

Lil Wayne confirmed that he had indeed held that suicide-watch job in a diary entry that appeared in "Gone 'Til November." As he revealed, he landed the job after attaining a perfect 100-percent score on a screening test for potential prison employment. "The job is basically to monitor the tier for an eight-hour shift and if someone wants to hang up [commit suicide], to not negotiate with them or try to talk them out of it, but just to alert an officer," he wrote in an excerpt appearing in Vulture. "Yeah, it's that real."

As days passed and Lil Wayne came closer to the end of his time in prison, toward the end of his sentence, he experienced a big adjustment to his situation. Remember when he was caught red-handed with that contraband MP3 player, for which disciplinary action had been promised? That punishment arrived during his final month of incarceration when he was required to spend his remaining days in solitary confinement. 

Even though his one-year sentence was shortened to eight months due to good behavior, The Guardian reported that Lil Wayne's solitary confinement — "the Bing," in Rikers parlance — meant he had to spend 23 hours each day in his cell, allowed to leave for just one hour of "recreation time" — during which time he was not permitted to fraternize with any of his fellow inmates. During that period, he was only allowed to exit his cell to take a shower, meet with a visitor, or be seen by the prison doctor; the only reason he hadn't served his sentence in solitary sooner was that the Bing had been occupied by other prisoners until then. 

One bonus, however, was that some of the corrections officers who oversaw him during that final month in the Bing brought him home-cooked meals — something that the rapper divulged in a "Gone 'Til November" diary entry, as reported by Complex.  

After eight long months at Rikers Island, the big day finally arrived. On November 4, 2010, Lil Wayne was released from prison. After his release, Lil Wayne addressed his time in the joint in a post on his prison website, WeezyThanxYou.com. "I was never scared, worried nor bothered by the situation," he wrote of spending eight months behind bars (reported by The Associated Press). According to members of his management team, he headed straight to his home in Miami, where a big party was awaiting to welcome him home.

Lil Wayne had more to celebrate than just his freedom; during his final month at Rikers, while he sat in solitary confinement, his album "I Am Not a Human Being" was released, skyrocketing to No. 1 on the Billboard 200.

While he was no doubt thrilled to be finally free, there was at least one aspect of prison life that he remembered fondly: Friday-night radio music parties. "On Fridays, we go to the club. You have a little AM/FM radio that you buy from commissary," he divulged during a post-release interview with Angie Martinez of radio station Hot 97 (reported by Vulture). As Wayne recalled, on weekends, from 10 p.m. until 2 p.m., Hot 97 would often broadcast live DJ sets from a nightclub — which he and other inmates would listen to on the tiny transistor radio. "And we be in the club, too, 'cause we locked in our cell," he added. 

In 2013, rapper Fat Joe was sentenced to four months in prison for neglecting to file income tax returns to the tune of more than $3 million. 

Prior to serving his sentence, he received some prison advice from fellow rapper/convicted felon Lil Wayne. During a 2022 appearance on Jada Pinkett Smith's "Red Table Talk," Fat Joe recalled visiting Wayne in prison, and being shocked to see him shackled up. "They had him, like, really chained up, like, Lil Wayne!" he said. "They had him like he was the killer of all, right?"

According to Fat Joe, Lil Wayne was his neighbor in Miami, and he shared his recollection of receiving a phone call from Wayne shortly before he was about to turn himself in to begin serving his own prison sentence. As he shared, Lil Wayne advised him to maintain a demeanor of humility while serving his time. "I was like, 'Yo, Wayne, what's up?' And he was like, 'Nah, man, I'm just telling you right now, be humble,'" Fat Joe recounted. "I said, 'How do you do it?' He said, 'Just be humble, bro. Don't go in there on somethin'. Just go in there humble. You know, if you be humble, they'll respect you.'"