30 Celebrities You'll Be Shocked to Hear Have Gone to Prison

30 Celebrities You'll Be Shocked to Hear Have Gone to Prison

Despite all the glitz and the glam that surround them, celebrities are human too. This just means that yes, they can make terrible decisions and mistakes too, some of which are punishable by law. Here are 30 celebrities that you may be surprised to learn have taken a trip down to the police station.

1. Robert Downey Jr.

Before his resurgence as Iron Man, Robert Downey Jr. struggled with drug addiction. He was arrested multiple times and served time in prison during the late 1990s and early 2000s for related offenses.

bermix-studio-Tb9sgkp77LM-unsplash.jpgPhoto by Bermix Studio on Unsplash

2. Martha Stewart

The home and lifestyle guru was convicted of insider trading in 2004. She spent five months in federal prison followed by home confinement and probation.

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3. Mike Tyson

Famed for his boxing prowess, Tyson was convicted of rape in 1992. He served three years of a six-year prison sentence.

1024px-Mike_Tyson_Wizard_World_Comic_Con_2015.jpgPhoto by Paula R. Lively from Zanesville on Wikimedia Commons

4. Wesley Snipes

The Blade actor faced charges for tax evasion. He was convicted in 2008 and served a three-year prison sentence.

1024px-wesleysnipes41969117570.jpgPhoto by Gage Skidmore from Peoria, AZ, United States of America on Wikimedia Commons


5. Lil' Kim

The rapper faced charges for perjury and conspiracy in 2005, leading her to be sentenced to one year and one day in prison for lying to a jury about a shooting.

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6. O.J. Simpson

Though famously acquitted in a 1995 murder trial, O.J. was later convicted in 2008 for armed robbery and kidnapping in Las Vegas. He served nine years before being granted parole in 2017.

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7. Paul McCartney

In 1980, the former Beatle was arrested in Japan for marijuana possession. He spent nine days in jail before being released without charges.

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8. Mark Wahlberg

Before his acting career, a young Wahlberg was involved in violent crimes. At 16, he was sentenced to two years for assault, though he served only 45 days.

markwahlberg14256596873.jpgPhoto by Eva Rinaldi  on Wikimedia Commons

9. Tim Allen

Before finding fame in comedy, Tim Allen was arrested in 1978 for drug trafficking. He served over two years in federal prison after providing names of other dealers in exchange for a reduced sentence.

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10. Tommy Lee

The Mötley Crüe drummer faced jail time in 1998 for assaulting his then-wife, Pamela Anderson. He served six months in county jail.

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11. Danny Trejo

Before becoming an iconic actor, Trejo was incarcerated multiple times for drug and robbery offenses. He turned his life around and is now a celebrated actor and advocate for rehabilitation.

1024px-dannytrejo26432404524.jpgPhoto by Gage Skidmore from Surprise, AZ, United States of America on Wikimedia Commons

12. James Brown

The Godfather of Soul had multiple run-ins with the law. In the 1950s, he served three years for armed robbery.

1024px-James_Brown_in_Concert.jpgPhoto by Robbie Drexhage on Wikimedia Commons

13. Tupac Shakur

The influential rapper and actor was convicted of sexual assault in 1995. He served nine months of a one-and-a-half to four-and-a-half year sentence.

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14. Christian Slater

In 1997, Slater was charged with assaulting his girlfriend and a police officer. He served three months in jail for the offenses.

christianslaterin2015cropped.jpgPhoto by Dominick D on Wikimedia Commons

15. Sean Penn

The Academy Award-winning actor was sentenced to 60 days in jail in 1987 following a series of altercations with paparazzi. Penn served 33 days of his sentence and was released for good behavior. Over the years, he has been involved in several other confrontations and legal issues.

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16. Lauryn Hill

The famed singer and rapper served a three-month prison sentence in 2013 for tax evasion. She was convicted for failing to file federal income tax returns over a period of several years.

2018_06_22_Lauryn_Hill_Cittadella-5.jpgPhoto by Città di Parma on Wikimedia Commons


17. Phil Spector

The legendary music producer was convicted of second-degree murder in 2009 for the death of actress Lana Clarkson. He was sentenced to 19 years to life and died while still incarcerated.

Phil_Spector_in_1965.jpgPhoto by Unknown photographer on Wikimedia Commons

18. David Cassidy

The "Partridge Family" star faced multiple DUI arrests. In 2014, he was sentenced to 90 days in rehab and five years probation after his third DUI arrest in as many years.

David_Cassidy_op_Schiphol_-_NA_-_926-2559.jpgPhoto by Hans Peters (Anefo) on Wikimedia Commons

19. Plaxico Burress

The NFL wide receiver accidentally shot himself in the leg with an unlicensed firearm in a New York nightclub in 2008. He served 20 months in prison for illegal weapons possession.

1024px-Plaxico_Burress_smiles.jpgPhoto by Jeffrey Beall on Wikimedia Commons

20. Nick Nolte

The esteemed actor was arrested in 2002 for driving under the influence of drugs. Although he avoided jail by entering a rehab program, he was later sentenced to three years' probation.

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21. Richard Hatch

The original "Survivor" winner was sentenced to 51 months in prison in 2006. He was convicted of tax evasion after failing to report his $1 million prize from the show.

the-new-york-public-library-kAJLRQwt5yY-unsplash.jpgPhoto by The New York Public Library on Unsplash

22. Meek Mill

The rapper has faced numerous legal issues, with the most notable being a controversial prison sentence for violating probation in 2017. Advocates rallied for his release, and he was freed in 2018.

meekmill%40madeinamerica2015vii23724077599.jpgPhoto by Chris Sikich from Philadelphia, USA on Wikimedia Commons


23. Boy George

The Culture Club frontman was sentenced to 15 months in prison in 2009 for falsely imprisoning a male escort. He served just over four months before being granted early release.

boygeorge6607691565.jpgPhoto by Eva Rinaldi  (1971–) on Wikimedia Commons

24. Lenny Bruce

The groundbreaking comedian faced multiple arrests in the 1960s for obscenity related to his performances. While he did serve time, many of these convictions were posthumously pardoned.

Lenny_Bruce_mugshot_1963.jpgPhoto by State of California on Wikimedia Commons

25. Macaulay Culkin

The "Home Alone" actor was arrested in 2004 for marijuana possession, possession of a medication without a prescription, and possession of paraphernalia. He received a deferred sentence and was given probation.

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26. Foxy Brown

The rapper served eight months of a one-year sentence in 2007-2008. She was convicted of violating probation from an earlier assault charge.

Foxy_Brown.jpgPhoto by Broward County Sheriff's Department on Wikimedia Commons

27. George Michael

The British pop star was sentenced to eight weeks in prison in 2010 for driving under the influence of drugs. He served four weeks before being released.

1024px-George-Michael-Impersonator.jpgPhoto by Evan-Amos on Wikimedia Commons

28. Randy Travis

The country music legend faced several alcohol-related arrests. In 2012, he was sentenced to rehab and probation following an arrest for DUI.

Randy_Travis_MCI_Center_In_Washington.jpgPhoto by Andy1981 on Wikimedia Commons

29. Mystikal

The rapper was sentenced to six years in prison in 2004 after pleading guilty to sexual battery and extortion. He was released on parole in 2010.

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30. Gary Dourdan

Best known for his role on "CSI: Crime Scene Investigation," Dourdan has faced multiple arrests over the years, primarily related to drug possession. While his legal troubles led to brief jail stints and probation, they have also impacted his acting career.

Gary_Dourdan.jpgPhoto by Palm Springs Police Department on Wikimedia Commons