24 Rappers Who Served Time in Jail: Their Worst Moments

There have been many musicians, singers, and actors who have been in trouble with the law, whether it’s for intoxication, drugs, and even violence, up to murder. Rappers are no different.

Here are 24 rappers who served time in jail.

1. T.I.

rapper TI on stage performing shirtless — Image from Shutterstock.

T.I., known for being a pioneer of trap music, a subgenre of hip hop, has had no string of instances with the law, and because of that, he has also had many cases that qualify him for our rappers who served time in jail list. His first prison sentence came in March 2004, after he violated his parole from a previous drug conviction.

While he was sentenced to three years, he only served a few months before he was released on probation. In 2008, because of a federal weapons charge, T.I. found himself being sent to prison again for one year and one day, a reduced sentence from ten years, thanks to a plea bargain.

Although he was released in March 2010, it was just a few months later that he was sentenced yet again to 11 months in prison on drug charges, which violated his parole. He only served a short period of that time, however, being released in August 2011 to spend the remainder of the sentence at a community living facility.

Although this is the last time he was imprisoned, T.I. has continually found himself in hot water for various things, so it seems only a matter of time before he is back there again.

2. Tupac

who killed tupac rappers who got shot — Rome, January 11, 2019: Collection of covers and cd inserts of the singer Tupac Shakur, considered by many to be one of the greatest hip hop artists of all time. selective focus. Image from shutterstock.

Tupac Shakur, may he rest in peace, was just in his early 20s when he became one of the rappers who served time in jail. On February 7, 1995, he was sentenced to prison for “an act of brutal violence against a helpless woman,” which included forcing her to perform oral sex. As a result, he was meant to spend anywhere between 18 months to four-and-a-half years in prison.

He only spent about six months, however, having successfully appealed his conviction.

3. Lil’ Kim

lil kim on the red carpet — LOS ANGELES – JUN 27: Lil Kim at the BET Awards 2021 Arrivals at the Microsoft Theater on June 27, 2021 in Los Angeles, CA. Image from Shutterstock.

As one of the few women to appear on our rappers who served time in jail list, Lil’ Kim became eligible in 2005 when she was convicted on three counts of conspiracy and one count of perjury, having lied to a federal grand jury regarding her involvement in a 2001 shooting outside of Manhattan.

As a result, she was sentenced to one year in prison, followed by 30 days of home detention and three years of probation. Uniquely, she is one of the few on our list who served her entire sentence, being released on July 3, 2006, although her Federal Bureau of Prisons supervision ended on August 2, 2006.

4. Bobby Shmurda

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As we’ll see with many on our list of rappers who served time in jail, Bobby Shmurda is almost as famous for his legal woes as he is for being a pioneer of Brooklyn drill music.

In December 2014, Shmurda was arrested and later convicted on several charges, including reckless endangerment, conspiracy to murder, and weapons possession. He spent more than six years in prison at the Clinton Correctional Facility for these charges. He was released in February 2021.

5. Gucci Mane

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Another “trap music” pioneer ends up on our list of rappers who served time in jail. Gucci Mane spent 90 days in a county jail in April 2001 on cocaine charges.

Four years later, he served another six months on aggravated assault charges, previously a murder charge that was dropped, following a shooting that occurred when a group of men attacked him outside his Georgia home.

He was later incarcerated again after violating his parole following his release from the aggravated assault charge, serving six months of his original one year.

Mane’s following jail sentence came in 2011 when he was sentenced to six months after pleading guilty to two counts of reckless conduct, two counts of battery, and one count of disorderly conduct. He was released on December 11, 2011.

His final long-term jail sentence happened in May 2014, when he pleaded guilty to possession of a firearm by a convicted felon. As a result, he spent two years in the United States Penitentiary in Terre Haute, Indiana, before being released on May 26, 2016.

6. Lil Wayne

lil wayne with a microphone and his hair flying in the wind — Chicago, Illinois / United States – Saturday, August 3rd, 2019: Lil Wayne performs at Lollapalooza in Grant Park, Chicago. Image from Shutterstock.

Regarded as one of his generation’s most influential hip-hop artists, Lil Wayne still proves to be that despite his legal issues. In 2010, he was sentenced to one year in prison on a weapons charge, which he served on Rikers Island, of which he only served eight months. This was his only stint in jail, however, despite his multiple drug and weapon charges over the years.

Then, on January 19, 2021, President Donald Trump’s last full day in office, he was pardoned of his most recent federal firearms charge, for which he pleaded guilty on December 12, 2020.

7. Fat Joe

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Joseph Antonia Cartagena, aka Fat Joe, known for such songs as “What’s Luv?” and “Flow Joe,” is another on our list of rappers who served time in jail and has had run-ins with police on more than one occasion.

However, he has only had to serve jail time for one of those occasions.

In December 2012, he pleaded guilty to tax evasion, having not paid income tax on more than $3 million in earnings between 2007 and 2019. In June 2013, he was sentenced to four months in prison, later serving from August 26, 2013, to November 28, 2013.

Related: Fat Joe’s Net Worth

8. Remy Ma

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Another female to get mixed up on our list of rappers who served time in jail is Remy Ma, most known for songs like “Whuteva,” “Lean Back,” and “Conceited.” Remy Ma was convicted on charges of attempted murder, assault, and criminal weapon possession and sentenced to eight years in the Bedford Hills Correctional Facility for Women.

This came following a shooting in Manhattan involving a verbal confrontation outside the Pizza Bar. She was later released after six years on August 1, 2014.

9. Beanie Sigel

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Beanie Sigel may have achieved fame as a rapper thanks to Jay-Z, but he has become more known for his many legal issues since 2002. With at least six arrests, which have resulted in approximately four years of federal or state prison time combined, it seems that it’s only a matter of time before he adds to those numbers.

Over the years, his jail time has been for charges like federal weapons, robbery, drug possession, and even failing to file taxes. Funnily enough, it was the latter for which he has spent the most time, being sentenced to 25 months in prison.

10. Max B

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Charly Wingate, aka Max B, is one of the most controversial to appear on our list of rappers who have served time in jail thus far and is one who remains in prison to this day. In mid-2009, Max B was sentenced to 75 years in prison. This was due to various conspiracy charges, including armed robbery, aggravated assault, felony murder, and kidnapping.

While he began his sentence shortly after, it was later revealed on September 16, 2016, that he took a plea bargain, reducing his sentence to 20 years for aggravated manslaughter. He is expected to be released in 2029.

11. Cassidy

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For singles like “Hotel” featuring R. Kelly, “Get No Better” featuring Mashonda, and “I’m a Hustla,” we have rapper Cassidy to thank. But, in 2005, he hit a low point when he and two other men shot at three other unarmed men during an argument that occurred in northwest Philadelphia.

Two months later, on June 9, 2005, Cassidy was arrested on charges of murder, attempted murder, aggravated assault, reckless endangerment, conspiracy, and weapons possession.

Seven months later, on January 26, 2006, Cassidy was convicted of involuntary manslaughter, aggravated assault, and possession of an instrument of crime. He served one month, in addition to the seven months he spent awaiting trial, and was released from the Curran-Fromhold Correctional Facility in Pennsylvania on March 2, 2006.

12. B.G.

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B.G., famously known for resigning from Cash Money Records in 2001 and starting his own label, Chopper City Records, was sentenced to 14 years in federal prison in February 2010 about relating to a 2009 traffic stop.

While it was a routine stop at first, a search of his vehicle revealed three guns, of which two were reported stolen. He was just recently released on September 5, 2023, after serving 11 of the original 14-year sentence.

13. Shyne

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Shyne has to be the most honorable of all the rappers who served time in jail. The rapper was arrested and sentenced to 10 years in prison back in 1999 on assault charges after an argument broke out at an area nightclub. Although he was deported to Belize upon his release in 2009, he turned things around, studying the Torah in Jerusalem.

He was appointed the Belize Music and Goodwill Ambassador in Belize and was even elected to the Belizean House of Representatives in the 2020 general election. Then, in June 2021 and February 2022, he was named Belize Leader of the Opposition and eventual leader of the Belize United Democratic Party.

14. Tay-K

a rapper with his face obscured in shadow — (No licensable photos available) Image from Shutterstock

Once again, we have someone on our rappers who served time in jail and is perhaps better known for his legal trouble than his actual musical work. Tay-K spent three months running from authorities in 2017 for his criminal activity. He was later found guilty of murder for his part in a 2016 robbery and home invasion, which resulted in the death of 21-year-old Ethan Walker. Tay-K was sentenced to 55 years in prison.

A few months later, in November 2019, he was indicted for a second murder charge, having allegedly shot 23-year-old Mark Anthony Saldivar. He is still awaiting trial for that offense as he continues his previous sentence.

15. 6ix9ine

6ix9ine the rapper on stage performing with Tekashi69 — Image from Shutterstock

Daniel Hernandez, better known as 6ix9ine, has made a name for himself, not just for his aggressive rapping style but also for his distinct rainbow-colored hair and multiple tattoos. Just as well-known is his string of legal issues and celebrity feuds. His first time in jail happened when he was only a minor because of assault charges and charges for selling heroin.

Ever since, he has been in and out of trouble, eventually being sent to jail in 2019 on gang violence charges. While he initially faced up to 47 years in prison, he got the shorter sentence because he testified against fellow gang members.

Because of the COVID-19 pandemic, 6ix9ine was released after one year and sentenced to home confinement for the remainder of his term because of his high risk of contracting the disease due to his pre-existing asthma condition. His home confinement period ended on August 1, 2020.

6ix9ine may face prison time again soon, as on October 15, 2023, he was arrested in the Dominican Republic on suspicion of assault against two music producers, but only time will tell.

16. Kodak Black

Lil Wayne wasn’t the only one on our list of rappers who served time in jail to get a last-minute pardon from President Trump. Kodak Black, known for the singles “No Flockin” and “Tunnel Vision,” was not entirely off the hook like Lil Wayne, however, as he was still facing criminal sexual assault charges at the time, for which he took a plea deal, avoiding prison and instead getting 18 months of probation.

Previously, he hadn’t been so lucky, serving prison time for possession of a firearm, robbery, battery, drug possession, and even the false imprisonment of a child.

17. Greedo

a silhouette of a rapper performing — (No licensable images available)Image from Shutterstock.

Greedo is one on our list of rappers who served time in jail and is still serving his sentence as of 2023. In 2018, he was sentenced to 20 years in prison for possession of a firearm and drugs.

18. Casanova

rapper cassanova on the red carpet in a colorful t shirt — Image from Shutterstock.

Casanova may have started to make a name for himself in 2016 with his first original song, “Don’t Run.” Still, it all went downhill in 2020, when he was indicted on Racketeer Influenced and Corrupt Organizations (RICO) charges through his “Untouchable Gorilla Stone Nation” Bloods gang.

He was sentenced to 15 years and eight months in prison on June 27, 2023, after surrendering to authorities on December 2, 2020.

19. Boosie BadAzz

boosie badazz the rapper on the red carpet — Image from Shutterstock.

Boosie BadAzz, formerly known as Lil Boosie, was sentenced on drug and gun charges in 2009, for which he served five years in prison. Later, while serving his time, he almost had more added when he found himself facing first-degree murder charges as well as further drug possession charges with the intent to distribute them.

He was, however, found not guilty. He was released from prison on March 5, 2014.

20. Suge Knight

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Suge Knight may not be a full-blown rapper, but he is considered a central figure of gangsta rap’s commercial success thanks to Death Row Records, for which he is co-founder and CEO.

Sadly, his further influence on the genre is delayed for several years, as he serves a 28-year prison sentence thanks to a fatal hit-and-run accident in 2015, resulting in the death of Terry Carter.

Related: Suge Knight’s Net Worth

21. YNW Melly

ynw melly's trial ynw melly sentencing ynw legal troubles — YNW Melly’s mugshot, image is in the public domain.

Of those on our list of rappers who served time in jail, YNW Melly has been in the news most recently for his crimes. In February 2019, YNW Melly was arrested and charged with two counts of premeditated murder. As he continues to face life imprisonment and even the potential death penalty, the decision has continued to be delayed by hung juries and the COVID-19 pandemic.

While the retrial was meant to begin in October 2023, that has since been changed to February 2024 by the judge.

22. Slick Rick

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Slick Rick, known for being a member of Doug E. Fresh & the Get Fresh Crew that brought about the classics like “The Show” and “La Di Da Di,” earned his spot on our rappers who served time in jail list in 1990 when he was charged with two counts of attempted murder as well as use of a firearm, assault, and criminal possession of a weapon. As a result, he spent five years in prison.

23. Meek Mill

rapper meek mill on stage performing — Image from Shutterstock.

Meek Mill, known for songs like “Amen” featuring Drake and “Tupac Back” and “Ima Boss,” both featuring Rick Ross, is another on our list of rappers who served time in jail and has been arrested on numerous occasions for various things.

His biggest run-in came in 2008 when he was convicted of possession of drug paraphernalia, as well as possession of a weapon, for which he was sentenced to 11 to 22 months in prison.

Meek Mill ultimately served seven months and was released in early 2009. In January 2023, he was pardoned by Pennsylvania Governor Tom Wolf for all his convictions.

24. Ja Rule

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To wrap up our rappers who served time in jail list, we have Ja Rule, ironically best known for his song, “I’m Real (Murder Remix),” as well as “Ain’t It Funny” and “Between Me and You.” His first prison term, two years, came in 2011 after he pleaded guilty to attempted possession of a weapon charge. Later, he was given an additional 28 months for tax evasion. He was released from prison on May 7, 2013.

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