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.
Grab your comfiest chair and sit down as we dive into 21 famous singers who served jail time.
1. Arthur Lee
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.
2. David Allan Coe
David Allan Coe is an infamous singer, crooning about being an outlaw after a twenty-year stint in prison. His list of crimes includes sentencing to reform school at nine years old, robbery, and possession of pornography, just to name a few of his wrongdoings.
3. Lil Wayne
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
Lohan is a part-time singer and 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
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
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
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.
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 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 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 and a few hours in jail on the island before he found freedom again.
11. Glen Campbell
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
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 has a complicated history, first sentenced to five years in prison for bringing a minor across the border to Mexico. After serving 20 months, he was sued by women claiming he put cameras in the bathroom to gawk at them, accused of child abuse, and convicted of drug charges, to name a few.
14. Wiz Khalifa
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
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 Combs
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.
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
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
Unbeknownst to many, the infamous Charles Manson was a singer and songwriter. He spent time in jail and was sentenced to death for murder and conspiracy to murder a cult he formed in the Los Angeles area.
20. Ian Brown
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 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.
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