It’s common to see the odd celebrity in the media that’s been acting out. But for some celebrities on our list, they’ve taken things to another level altogether and have really broken bad. Some were facing jail time even before they achieved celebrity status. From tax evasion to drug possession, violence to DUIs, not all celebrities play by the rules. Despite their wealth and resources, including having access to the best lawyers available, these celebrities haven’t managed to avoid prison or jail.
1. Paul McCartney – 9 Days
In 1980, music legend McCartney was arrested at Tokyo’s Narita International Airport for his attempt at bringing half a pound of marijuana into the country. He served 9 days in prison before the authorities released him, deeming that enough time for McCartney to have learned his lesson.
2. Lauryn Hill – 3 months
Like most of us, celebrity singer Lauryn Hill doesn’t enjoy paying her taxes. When Hill did not file her tax returns, she was given a three year house arrest, along with three years on probation.
3. Paris Hilton – 45 Days
Hilton was incarcerated to 45 days in the slammer after violating her probation relating to a driving under the influence conviction in 2006. She also has a couple of arrests relating to drug possession under her belt.
4. Kiefer Sutherland – 48 Days
In 2007, actor Kiefer Sutherland served a 48 day sentence for driving under the influence of alcohol and for violating probation. Sutherland served food to other inmates whilst incarcerated and was credited for his politeness and his willingness to cooperate as an inmate.
5. Martha Stewart – 5 Months
Stewart was convicted in 2003 and was sentenced to prison for five months and served a month under house arrest. She was also given two years probation for securities fraud, obstructing justice and several lesser crimes.
6. Lil Kim – 1 Year
In 2005, rap artist Lil Kim served one year in prison for lying to a jury about a friends’ involvement in an earlier shooting. During her incarceration, Kim released her fourth album.
7. Wesley Snipes – 3 years
In 2006, actor Wesley Snipes was charged with failing to file his tax returns. In 2008, Snipes was incarcerated for 3 years for his convictions and started his prison sentence in December 2010. He was later released in April 2013.
8. Christian Slater – 3 Months
Whilst under the influence of cocaine, Hollywood actor, Slater, assaulted his girlfriend and a police officer in 1997, landing him three months in jail
9. Fat Joe – 4 Months
In 2013, celebrity rapper, Fat Joe, was arrested and sent to prison for four months after pleading guilty to tax evasion. He was also arrested in 1998 for assault charges and was even named as a witness in two murder cases.
10. Lindsay Lohan – 210 Days
Model and actor, Lindsay Lohan, was incarcerated to serve a day in jail as well as being given 36 months probation, several days community service and a court ordered alcohol awareness and rehab course. In 2010, she was sentenced to 90 days in jail for violating her probation and missing alcohol counseling sessions. In 2011, Lohan gets another 120 days in jail for her drink driving probation, along with 480 hours community service.
11. Michelle Rodriguez – 180 Days
In 2007, Rodriguez violated her probation when she failed to provide evidence of her completing community service relating to a drinking under the influence conviction. She also admitted to consuming alcohol whilst wearing an alcohol monitoring device. She was incarcerated for six months in jail before being released.
12. 50 Cent – 6 Months
In 1994, rapper and actor 50 Cent served six months in a jail shock boot camp for selling cocaine and possessing heroin and a starter gun. Cent was lucky, he could have been sentenced for up to nine years.
13. The Notorious B.I.G – 9 Months
Before The Notorious B.I.G was murdered, he served 9 months in jail for selling crack cocaine in 1991.
14. Jamie Waylett – 12 Months
Harry Potter actor, Jamie Waylett was sentenced to two years in prison in 2012 for his role in the London riots. The actor also received a 12 month sentence for handling stolen goods and a two year term for violent disorder.
15. Teresa Giudice – 15 months
Known for starring in reality TV show, The Real Housewives, Teresa was given a 15 month prison term for fraud. Taking multiple loan and credit cards out just before posting for bankruptcy, Teresa was released from prison after serving 11 months of her sentence.
16. Robert Downey Jr – 15 Months
Celebrity actor, Downey, was sentenced to prison time in 1997 and 1998 for drug and gun possession and breaking into a neighbour’s home. After failing to provide a drugs test whilst being on probation, Downey was jailed and then ordered into a treatment facility in state prison in 1999.
17. Mark Wahlberg – 2 years
At the age sixteen, actor Mark Wahlberg was convicted of assault for beating up two Vietnamese men with a stick while shouting racial remarks. Mark was given a two year sentence but was only imprisoned for 50 days. Taking in to account the fact that Mark blinded one of the victims, he was lucky to get off so lightly.
18. 2Pac – 11 months
In 1994, rapper and actor, 2Pac, was convicted of sexual assault and was sentenced to four and a half years in prison. He was released after serving 11 months before being bailed out by Suge Knight.
19. James Brown – 6 Years
In 1988, legendary singer, Brown, was sentenced to over six years in prison for aggravated assault and failing to stop for a police officer. Brown was released from jail after three years. In 1998, Brown was charged again with drug possession anď was ordered on to a drug rehabilitation course.
20. Mike Tyson – 6 Years
Celebrity boxer, Mike Tyson was convicted of rape in 1992 and was imprisoned for ten years. The judge suspended the last four years and Tyson was paroled after serving three years.
21. Tim Allen – 2 Years
According to wikipedia Back in ‘78, actor Tim Allen was caught at the airport with a whooping 1.43lb of cocaine. Tim was staring life imprisonment in the eye, however was offered a deal to reduce his prison sentence from three to seven years. He was later released after only serving two years.
22. Bill Cosby – 10 Years
In 2018, actor and entertainer Cosby was sentenced to 3 to 10 years in prison for the drugging and sexual assault on a woman at his home 14 years prior. Andrea Constand, Cosby’s victim, was in court to witness the sentencing.
23. Danny Trejo – 11 Years
Real life badass turned Hollywood celebrity, Trejo, was imprisoned for 11 years in the ‘60s for armed robbery and drug offences. He picked up his career in acting on his release.
24. O.J Simpson – 9 Years
Despite Simpson being most likely guilty of murder, most of us will already be aware of his acquittal in the 1995 trial of the century. However, in 2008, Judge Jackie Glass sentenced Simpson to 9 to 33 years in penitentiary for a range of charges including armed robbery, kidnapping, conspiracy and assault with a deadly weapon. O.J Simpson was released from prison October 1 2017