20 Celebrities Who You’ll Be Shocked to Hear Served Major Prison Time

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Celebrities can get into trouble too! While we tend to assume that fame affords a few get out of jail free cards, a number of celebrities have served real time in the big house for their actions.

These twenty stars, which include everyone from musicians to Oscar-winning actors, have landed themselves in prison—for a wide range of offenses. Some of them have since reforged their careers and moved on from mistakes in the past…others, not so much!


In his earlier years before becoming a celebrity, actor Mark Wahlberg was sentenced to two years in prison after assaulting two Vietnamese men. He ended up serving 45 days of his sentence.

Sean Penn, an Oscar-winning actor, was sentenced to 60 days in jail after attacking an extra on the set of Colors. He was, however, released early and did not serve the full original sentence.

In 1997, actor Christian Slater served 3 months in prison for the assault of his girlfriend at the time. He had previously spent 10 days in jail in 1989 for drunk driving.

Rapper and performer Lil’ Kim served a year in prison for lying to a grand jury about her friends’ involvement in a 2001 shooting outside of a Manhattan radio station.

Tim Allen’s trouble with the law took place before he gained fame. In 1978, he was sentenced to prison for drug trafficking. Allen served almost two and a half years before being released on parole in 1981.

O.J. Simpson was found not guilty of the murder of both his wife, Nicole Brown Simpson, and Ronald Goldman in 1995 after a highly publicized trial. He was, however, sentenced to 33 years in prison for armed robbery and kidnapping in 2008. He was released on parole in October 2017.

Musician Chris Brown was imprisoned for several months in 2014 after violating probation – a probationary period given after his violent assault of then-girlfriend Rihanna in 2009.

Jamie Waylett, whom you might recognize as teenage wizard and Slytherin cohort Crabbe from the Harry Potter movies, was sentenced to 2 years in prison for participating in a London riot in 2011.

In 2010, actress Lindsay Lohan served two weeks of jail time for missing mandatory classes and meetings in the wake of her DUI. She had been in and out of rehab, and in trouble with the law, since 2007.

Teresa Giudice of The Housewives of New Jersey served 11 months in prison for tax fraud in 2015.

Professional boxer Mike Tyson was convicted of rape and subsequently served three years in prison in the 1990s; though he continues to maintain that he was innocent of the charges.

Musician Tommy Lee served 6 months in prison in 1998 for the assault and battering of his wife at the time, Pamela Anderson.

Actor Wesley Snipes was sentenced to 3 years in prison in 2009; his sentence began in 2010 and he was released in 2013. The actor was convicted for failing to file his tax returns from 1994 through 2000.

Lauryn Hill, singer and Fugee band member, was sentenced to 3 months of prison in 2013 for tax evasion. Upon her return, Hill immediately went back to work making music (releasing a single the same day as her own release!)

Businesswoman and television personality Martha Stewart served about 5 months in prison from 2004 into 2005. She was released to another five months of house arrest in March 2005.

Actor Robert Downey, Jr. served almost one year in prison after violating his probation on drug charges in 1999.

The late James Brown, legendary singer and band leader, had several run-ins with the law throughout his life. In 1988, he was sentenced to 6 years in prison on charges related to drugs, and failing to stop for police during a high-speed car chase.

Rapper and actor Ja Rule served 2 years in prison, beginning in 2011, for possession of an illegal gun and tax evasion. He was released in 2013.

Lillo Brancato Jr., most known for acting in The Sopranos, served in prison for a total of 8 years for the second-degree murder and burglary of an off-duty police officer. He was released in 2013.

Phil Spector, musician and record producer, was found guilty of the murder of actress Lana Clarkson in 2009. Spector is now serving 19 years to life in prison.