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23 Famous Singers Who Served Jail Time

singers who served Jail time
CAP D'ANTIBES, FRANCE - MAY 17: Paris Hilton arrives at the amfAR Gala Cannes 2018 at Hotel du Cap-Eden-Roc on May 17, 2018 in Cap d'Antibes, France. Image from Shutterstock.

Not every singer has a perfect background, and some surprising faces have spent time behind bars. Luckily, most of these singers learned their lesson and changed their way after serving their time and resuming their careers.

But some artists are still locked up today for more nefarious reasons we will explain below. Grab your comfiest chair and sit down as we dive into 23 famous singers who served jail time.

1. Arthur Lee

arthur lee in the band love
Image of the band Love featuring Arthur Lee in 1967. Image is in the public domain.

Arthur Lee is one of the most famous singers who served jail time, serving twelve years for the negligent discharge of a firearm. He was previously convicted of assault and drug charges, allowing the minor crime to land a prison sentence for Lee based on California’s Three Strike Law. Lee is best known as the singer of Love, whose 1967 album Forever Changes often makes the top 10 albums of the 60s lists.

2. David Allan Coe

david allan coe poster
David Allan Coe poster from 1976. Image is in the Public Domain

Infamous country singer David Allan Coe has always used his time in prison to puff up his outlaw credentials. His list of crimes includes burglary and auto theft. He also claims that he was on death row for killing a man in prison, but there’s no evidence that this was the case.

3. Lil Wayne

lil wayne
Chicago, Illinois / United States – Saturday, August 3rd, 2019: Lil Wayne performs at Lollapalooza in Grant Park, Chicago. Image from Shutterstock.

In 2007, Lil Wayne was arrested and pleaded guilty to possession of a weapon after a firearm was located on his tour bus. As a result, he served eight months on Rikers Island out of a one-year sentence for the discovery of the firearm.

4. Lindsay Lohan

Lindsey lohan
Lindsay Lohan at Vanity Fair Oscar Party, Mortons Restaurant in West Hollywood, Los Angeles, CA, Sunday, March 05, 2006. Image from Shutterstock.

Actress and singer Lindsay Lohan spent 84 minutes in jail in 2007 after being arrested and pleading guilty to the use of cocaine and DUI. She’s been arrested multiple times since then for crimes like driving under the influence and public altercations.

5. Paul McCartney

paul mccartney
Washington DC. USA, 4th July, 1990 Paul McCartney performs at the Fourth of July concert in the Robert F. Kennedy football stadium. Image from Shutterstock.

Shockingly, Paul McCartney is on our list of famous singers who served jail time. In 1980, McCartney toured Japan but had to stop and spend ten days in jail when authorities located eight ounces of marijuana in his suitcase.

6. Lil’ Kim

lil kim
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.

In 2001, rapper Lil’ Kim lied on the stand about a shootout to protect her friends from more serious repercussions. She was arrested for lying to the Grand Jury and received a sentence of one year and one day in prison, along with paying a $50,000 fine.

7. 50 Cent

50 cent
50 Cent shares the headlining Bill with his group G-Unit for the Radio One BirthDay Bash Atlanta Georgia June 18, 2016 At Phillips Arena. Image from Shutterstock.

Back in 1994, famous rapper 50 Cent was arrested based on selling four crack cocaine vials to an undercover officer As a result of his controlled substance charge, the rapper was sentenced to a three to nine-year prison stint but ended up going through the SHOCK program instead.

8. Tupac

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. Image from Shutterstock.

Tupac Shakur racked up many counts in his life, starting with a count of sexual assault in 1995 that landed him eleven months in jail. Unfortunately, his involvement in rival factions and gang violence eventually led to his assassination before he redeemed himself after his jail experience. 

9. Johnny Cash

johnny cash
Berlin, Germany – October 12, 2019: Compact disc for sale The Ultimate Johnny Cash Collection and others. Image from Shutterstock.

Johnny Cash always maintained a romantic outlaw image and ran into the law several times for issues with reckless driving, public drunkenness, and drug possession. He went to jail seven times between 1959 through 1968 for his various experiences, though he only stayed for a maximum of one night each visit.

10. Willie Nelson

willie nelson
Arrington, VA/USA – 9/7/2014 : Willie Nelson performs at LOCKN’ Festival in Arrington, VA. Image from Shutterstock.

Willie Nelson has sat behind bars multiple times for possessing marijuana. His most memorable arrest occurred in 1977 when a tour to the Bahamas led to a discovery of marijuana in Nelson’s pants. He spent a few hours in jail on the island before he found freedom again. 

11. Glen Campbell

glen campbell
LOS ANGELES – FEB 12: GLEN CAMPBELL, KIM & ASHLEY arriving to Grammy Awards 2012 on February 12, 2012 in Los Angeles, CA. Image from Shutterstock.

Glen Campbell was pulled over and arrested for DUI and assault on an officer charges in 2011 after a reported hit-and-run. Campbell spent ten days in jail after pleading guilty to the DUI and confessing to hitting another vehicle and driving away from the scene.

12. Nick Carter

nick carter
Nick Carter on stage for NBC Today Show Concert Series with the BACKSTREET BOYS, Rockefeller Center, New York, NY, June 10, 2005. Image from Shutterstock.

Backstreet Boys singer Nick Carter spent time in jail back in January 2016 after being accused of involvement in a Florida bar brawl. He didn’t spend very long behind bars and hasn’t been back since his arrest in The Sunshine State.

13. Chuck Berry

chuck berry statue
ST LOUIS MISSOURI – MAY 2018: Chuck Berry Statue in May 2018 in St. Louis, Missouri. The 8-foot-tall bronze statue stands on Delmar Blvd near the Ackert Walkway. Chuck Berry was born in St. Louis. Image from Shutterstock.

Chuck Berry was first sentenced to five years in prison for bringing a minor across state borders in 1960. It was a ticky-tack charge that was likely racially motivated. He served 20 months. Years later, he was sued by women claiming he put cameras in the bathroom at his restaurants to gawk at them.

14. Wiz Khalifa

wiz khalifa
PRAGUE, CZECH REPUBLIC- JUNE 28 2018: Wiz Khalifa raps on a stage with his band at the Aerodrome festival in Prague, Czech Republic. Image from Shutterstock.

Wiz Khalifa is another famous singer who served jail time, known for being very open about his marijuana use to his fans and the general public. His use led to an arrest in North Carolina in 2010 for marijuana possession and another in 2014 after TSA located marijuana in Texas.

15. Mac Miller

mac miller
Mac Miller kicked off his tour with a hometown performance in Pittsburgh September 18 at Stage AE. Miller is touring in support of his latest album, The Divine Feminine, released September 16. Image from Shutterstock.

The late Mac Miller spent time in jail for drunk driving and a hit and run in 2018. This arrest occurred a few months before his untimely overdose and resulted in a small amount of jail time for his recklessness. 

16. Sean “P Diddy” Combs

sean combs
LOS ANGELES – FEB 13: Sean “Puffy” Combs arrives to the 2011 Grammy Awards on February 13, 2011 in Los Angeles, CA. Image from Shutterstock.

Rapper Sean Combs went to jail in 2015 after using a kettlebell to assault a football team coach at UCLA, where his son played the sport. He spent time in jail and escaped a prison sentence with a year of anger management courses. 

17. XXXTentacion

A mugshot of Jahseh Onfroy, better known as rapper XXXTentacion, after being arrested for domestic violence in October 2016. Image by the Florida State Department.

The late XXXTentacion is another of our famous singers who served jail time, serving in 2016. He was there for six months after being charged with assault of a pregnant woman, witness tampering, false imprisonment, and domestic assault by strangulation.

18. Paris Hilton

paris hilton
CAP D’ANTIBES, FRANCE – MAY 17: Paris Hilton arrives at the amfAR Gala Cannes 2018 at Hotel du Cap-Eden-Roc on May 17, 2018 in Cap d’Antibes, France. Image from Shutterstock.

Hilton was first arrested under suspicion of DUI, which was reduced to reckless driving and led to a three-year probation for the pop singer. A month later, she drove with a suspended license and spent 45 days in jail.

19. Charles Manson

Charles manson
Charles Manson, April 1968 mugshot. Image by the California Department of Corrections.

Unbeknownst to many, the infamous Charles Manson was a singer and songwriter. He spent most of his life in jail for the Tate-LaBianca murders.

20. Ian Brown

ian brown
BUDAPEST, HUNGARY, AUGUST 10: Ian Brown and the Stone Roses play live in concert at the annual Sziget Music Festival on August 10, 2012 in Budapest, Germany. Image from Shutterstock.

Ian Brown, a singer for The Stone Roses, served in jail and prison. He spent four months behind bars for threatening to kill a stewardess and pilot during an airline flight.

21. R. Kelly

R Kelly Performs on stage at the FOX Theater on December 27, 2016 in Atlanta Georgia – USA. Image from Shutterstock.

R. Kelly was found guilty of several charges, including racketeering, having sex with underage girls, and the sexual exploitation of children in 2021. As punishment, he received a 30-year sentence which he will serve at Butner. Needless to say, we won’t be seeing any new music from him anytime soon. 

22. Gary Glitter

gary glitter arriving at an event in 1990
Image from Shutterstock.

British singer Gary Glitter is no stranger to time behind bars. With two sentences under his belt and one currently being served, it’s unlikely we will see him on the stage again anytime soon. Which is a good thing, as all of his charges have to do with child abuse and rape of a minor.

23. Merle Haggard

merle haggard on the red carpet
Image from Shutterstock.

Widely regarded as one of the best country music singers of all time, it might be a surprise to discover that he is also one of our famous singers who served jail time. Convicted of a robbery in 1957, Haggard was behind bars for three years before he was released to resume his budding career.

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Written by Hope Davis

Long-time music lover Hope became a full-time writer in 2020 after being laid off from her regular job due to COVID-19. She now spends her time traveling the world to see her favorite bands while writing about them!


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