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Mark Wahlberg -

Mark Wahlberg has a history of addiction, and was accused of attacking two Vietnamese men while high on PCP in 1988. He was convicted and sentenced to two years in prison, but only served 45 days. 

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Felicity Huffman - Actress Felicity Huffman was at the center of the college admissions scandal that hit the headlines in 2019. Huffman and a number of other wealthy parents were convicted of conspiracy to influence college admissions at top universities for the benefit of their children.

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Huffman was given a 14-day sentence, as well as 250 hours of community service and a US$30,000 fine.

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Sean Penn -

Sean Penn has drawn negative press on multiple occasions for violent outbursts. In 1987 he was sentenced to 60 days in jail for punching an extra on the set of the movie 'Colors.' He was on probation for two other assaults at the time. 

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Christian Slater -

In 1997, Christian Slater was arrested on charges of punching his girlfriend and then assaulting a police officer while under the influence of drugs and alcohol.  He was convicted and sentenced to three months in prison followed by three months in rehab. 

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Chris Brown - Chris Brown was sentenced to five years probation, community service, and counseling and rehabilitation for the 2009 assault on Rihanna. In 2013 he violated the terms of his probation by getting kicked out of rehab, and had to spend several months in jail.

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Martha Stewart -

Martha Stewart is an incredibly wholesome TV personality and aficionado in the realms of home, cooking, and lifestyle. It's a surprise to learn that she was involved in an insider trading scandal in 2003. 

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Martha Stewart -

She was charged with securities fraud, obstruction of justice, and conspiracy. Stewart spent five months in prison and another five under house arrest. 

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Kiefer Sutherland - In 2007, Kiefer Sutherland spent 48 days in jail for driving under the influence and violating the terms of his probation for a previous charge. He served his time and then had to take part in an 18-month alcohol education program.

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Robert Downey Jr. - Robert Downey Jr. was frequently in trouble with the law during the height of his addiction. He was arrested on multiple drug charges and eventually spent almost a year in prison after violating his parole.

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Mike Tyson - Mike Tyson served three years in prison in the 1990s for the rape of an 18-year-old girl. He has always maintained that he was falsely accused.

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Lauryn Hill -

Singer and activist Lauryn Hill was sentenced to three months in prison in 2013 for not paying her taxes. She served her time and soon after released the song 'Consumerism.' 

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Phil Spector - Disgraced music producer Phil Spector was famous for working with some of the greatest musicians of the 20th century, including The Beatles. In 2009 he was convicted of the murder of actress Lana Clarkson.

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Phil Spector -

Clarkson was found dead in his mansion with a gunshot wound to the face. Spector claimed it was an accidental suicide, but was convicted of murder. He died in jail on January 16, 2021. 

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O.J. Simpson - O.J. Simpson was famously found innocent of the murder of his ex-wife Nicole Brown Simpson, but he ended up in prison for a different crime the following decade. In 2008 he was sentenced to 33 years in prison for armed robbery and kidnapping. He served nine years and was released in 2017.

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Lindsay Lohan - Lindsay Lohan went through a rough period while struggling with addiction and was charged with a DUI in 2007. She was sentenced to two weeks in jail for failing to attend mandatory alcohol education classes.

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Wesley Snipes -

Wesley Snipes served three years in prison between 2010 and 2013. He was convicted of failing to pay his taxes from 1994 to 2000. 

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Tim Allen -

Tim Allen is known for playing Santa Claus and the handyman on 'Home Improvement,' but before his acting days he was arrested for drug trafficking. He was caught with hundreds of kilos of cocaine at an airport and spent two and a half years in prison before being released in 1981. 

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50 Cent -

Rapper 50 Cent was incarcerated for six months when he was only 16 years old. He was sent to a correctional facility for minors after he was convicted of several drug related offences. 

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James Brown - James Brown was on probation for drug offences in 1988 when he went on a crime spree that allegedly involved assault and battery, and refusing to stop for police during a high speed chase. He was charged to six and a half years in prison, but got out after three.

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Lil' Kim - Rapper Lil' Kim spent a year in prison after she was charged with perjury. She admitted to having lied to a grand jury about her friends' involvement in a 2001 shooting. She was also ordered to a pay a US$50,000 fine.

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Ja Rule -

Rapper and actor Ja Rule was sentenced to two years in prison for possession of an unauthorized gun in 2010. While serving his sentence, he was sentenced to a further 28 months for not paying his taxes. 

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Tommy Lee - Mötley Crüe drummer Tommy Lee was sentenced to six months in prison in 1998. He was charged with the assault and battery of his wife, Pamela Anderson.

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Danny Trejo - Danny Trejo was in and out of prison in the 1960s prior to his film career. He served time for crimes including burglary, assault, and drug possession.

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Tom Sizemore -

Troubled actor Tom Sizemore, best known for his role in 'Saving Private Ryan' (1998) has a long history of drug and domestic violence arrests. He was sentenced to 16 months in prison after he was found in possession of methamphetamines, which violated the probation of a previous drug-related conviction. 

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Monica Bedi -

Indian actress Monica Bedi spent two years in a Portuguese prison for using forged travel documents. She was arrested alongside her long-term partner Abu Salem, a known gangster and terrorist. 

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Dustin Diamond - The late 'Saved by the Bell' star Dustin Diamond served four months in prison in 2016. He was charged with disorderly conduct and carrying a concealed weapon, after an incident in a bar where he was allegedly found carrying a knife.

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Lillo Brancato Jr. -

Actor Lillo Brancato Jr. got a few good acting roles in the late 1990s and early 2000s, scoring a part in 'The Sopranos' and a Robert De Niro film. He later struggled with addiction and he and a friend broke into a house to steal prescription drugs in 2005. An off-duty police officer came to the scene and was shot and killed by Brancato Jr.'s friend. Brancato Jr. was sentenced to 10 years in jail for his role in the incident. 

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Mike 'The Situation' Sorrentino -

'Jersey Shore' personality Mike "The Situation" Sorrentino was sentenced to eight months in prison in 2018 for failing to pay his taxes. 

Sources: (Ranker) (22 Words) (The Guardian) 

See also: Bruce Springsteen and other celebs arrested for drunk driving

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