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Lil Wayne Was Sentenced to Jail 10 Years Ago — Look Back at the Rapper's Legal Troubles

Oyin Balogun
Nov 20, 2020
12:00 P.M.

Iconic rapper Lil Wayne has achieved unprecedented success in his music career. However, his career has been tainted by numerous run-ins with the law, including a one-year jail sentence in 2010.


Talented rapper Lil Wayne began his career in 1995 at the age of 12, when he was signed by music mogul Birdman as the flagship member of Cash Money Records.

Over the last two decades, Lil Wayne achieved massive success while signed to Cash Money Records and is regarded as one of his generation's most influential rappers.

Lil Wayne at the Lollapalooza Music Festival at Grant Park on August 03, 2019 | Photo: Getty Images

Lil Wayne at the Lollapalooza Music Festival at Grant Park on August 03, 2019 | Photo: Getty Images

Some of his ardent supporters even argue that he is the greatest rapper of all time. The fact that there is even a case speaks volumes of his immeasurable impact in the rap game, especially from the mid-2000s to late 2000s.

Over the years, there have also been concerns over Lil Wayne's mental health. During a 2018 interview, the rapper confessed that a childhood accidental gunshot wound was a suicide attempt.


However, his meteoric rise to fame was fraught with frequent run-ins with law enforcement agencies and eventually culminated in a one-year prison sentence in 2010.



Lil Wayne's troubled history with law enforcement dates back to July 22, 2007, when the rapper was arrested after his first headlining concert in New York.

The New York Police Department discovered Lil Wayne and an unidentified man smoking marijuana near a tour bus. After searching the bus, police found a .40 caliber pistol.

Even though Wayne's lawyers argued that the gun did not belong to him, the rapper was subsequently charged with criminal possession of a loaded weapon.


In October 2009, after DNA evidence linked the gun to the controversial rapper, he pleaded guilty to felony gun possession. Later that year, Wayne appeared before a court, and his sentencing date was set for February 9, 2010.

After his sentencing date was adjourned two times due to Wayne undergoing some dental work and a fire accident in the courthouse, he was finally sentenced to a one-year prison term.


In 2010, the award-winning rapper spent eight months at Rikers Island jail on a weapons charge. Despite detailing the difficult experience in his 2016 memoir titled "Gone' Til November," Wayne is still towing the road that got him in jail the first time.

Last year, Lil Wayne refused to perform at the Rolling Loud Music Festival in Miami after being subjected to security personnel or police search at the music fest venue.


In December 2019, Wayne was charged with weapons possession after Miami-Dade police and FBI agents found a gold-plated handgun in his luggage following a search of his private jet in Miami.

Due to his previous criminal record, Wayne is prohibited from possessing a firearm and faces as much as ten years in prison if he is convicted.



Lil Wayne's prison stint was one of the major events in the entertainment industry in 2010. Even for the rapper, it was a genuinely humbling experience, and he has been very vocal about those eight months at Rikers Island jail.

Despite being sentenced to a one-year jail term, the "Lollipop" rapper was released on November 4, 2010 — four months early, on good behavior.


Since his release, the rapper had been feeding the media with snippets from his time in incarceration. In 2016, Wayne dropped all the juicy details in his tell-all memoir, which featured a collection of his prison diaries.

The book revealed Wayne's struggles with coping with not just the rules in prison but the limited freedom. In one of the notes, Wayne wrote:

"I'm eating Oreos and drinking grape Kool-Aid as I write this right now. This is the kind of [expletive] that has become worth writing about: eating Oreos and drinking grape Kool-Aid."


During his stay in prison, Wayne got his spirit lifted with visits from P. Diddy and Kanye West — even though they were subjected to body searches. A particularly low point for the rapper was finding out that Drake had slept with his girlfriend in the past.

While in prison, Wayne did some writing and emerged with a new album. However, in recent years, his career has stalled due to a combination of factors, including his health troubles and hugely publicized dispute with label boss Birdman.


Wayne was at the peak of his fame when he was sentenced to a year in prison in 2010. Following his release from prison, Wayne immediately hit the ground running with the release of "Tha Carter IV" in 2011.

The album did considerably well, with hits like "Mirror" enjoying massive airplay. Wayne was scheduled to drop "Tha Carter V" in 2012, but the album was delayed due to disputes with his label boss Birdman.


Wayne's dispute with Birdman continued to slow down his career by delaying his album release or any other meaningful content from the rapper.


The "Mirror" rapper's struggles with his health also threatened his hugely successful career. Since his release from prison, Wayne has been hospitalized for seizures at least five times, raising concerns over his addiction to codeine.

In 2013, during an interview with Katie Couric, Wayne revealed that he had suffered seizures since he was a child. However, he claimed he had reduced his consumption of lean due to his doctor's advice.


Over the years, there have also been concerns over Lil Wayne's mental health. During a 2018 interview, the rapper confessed that a childhood accidental gunshot wound was a suicide attempt.

Despite all the drama and negative press surrounding Lil Wayne in the last decade, the rapper seems to be finally getting back on track.

After freeing himself from his Cash Money contract in June 2018, the hugely-anticipated "Tha Carter V" debuted at the Billboard top spot in September that year. Wayne's loyal fans hope that he would repay their faith in him in the coming years.

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