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Sean Penn -

Sean Penn has on several occasions drawn negative press over violent outbursts. In 1987, he was sentenced to 60 days in jail for punching an extra on the set of the movie 'Colors' (1988). He served 33 days before being released. At the time, he was on probation for two other assaults. 

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Tory Lanez -

The Canadian rapper was convicted in the Los Angeles County Superior Court of three felony charges related to shooting fellow musician Megan Thee Stallion in 2020. He shot her in the feet during an argument between the pair after a party. On August 8, 2023, he was sentenced to 10 years in prison.

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Allison Mack -

In 2021, 'Smallville' actress Allison Mack was sentenced to three years behind bars for her role in a sex-trafficking case tied to the cult-like group NXIVM. She was released early in July 2023. 

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Martha Stewart -

In 2003, the wholesome TV personality was involved in an insider trading scandal. 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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Chris Brown -

For the 2009 assault on Rihanna, Chris Brown was sentenced to five years probation, community service, and counseling and rehabilitation. In 2014, he violated the terms of his probation by getting kicked out of rehab, and was sentenced to 131 days in jail. Brown was granted early release, but was still on probation. 

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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 probation from a previous charge. After serving his time, he took part in an 18-month alcohol education program.

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Mike Tyson -

Mike Tyson served three years in prison in the '90s for the sexual assault of an 18-year-old girl. He claims that he was falsely accused.

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Mark Wahlberg -

In 1988, when Mark Wahlberg was 16 years old, he attacked two Vietnamese men in separate incidents on the same day, beating one unconscious and punching the other in the eye, while using racial slurs. He was charged with attempted murder, and convicted on two counts of assault and battery. He was sentenced to two years in prison, but only served 45 days. He was also convicted of contempt of court for violating a civil rights injunction from two years earlier, when he and some friends chased a group of Black children, calling them the N-word.

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Robert Downey Jr. -

Robert Downey Jr. was arrested on multiple drug charges during the height of his addiction. He breached probation three times by failing to submit drug tests. When he appeared in court again in 1999, Downey was sentenced to three years in prison. He served 15 months. 

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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 released her song 'Consumerism' soon after serving her time.

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Tim Allen -

Before his acting days, Tim Allen was arrested for drug trafficking. He was caught with hundreds of kilos of cocaine at an airport and spent two years and four months behind bars. He was released in 1981. 

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Danny Trejo -

During the '60s, Danny Trejo was in and out of prison for drug and theft offenses before he started his acting career. During one of his stints in prison in 1961, he even came across one of the most famous criminals in history: Charles Manson.

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Bill Cosby -

In 2018, the actor was sentenced to 10 years in prison for drugging and sexually assaulting Andrea Constand at his home in 2004. In 2021, the conviction was overturned and Cosby was released from prison.

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Felicity Huffman -

Actress Felicity Huffman was at the center of the 2019 college admissions scandal. 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. 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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Lori Loughlin -

Like Huffman, Aunt Becky of 'Full House' was also implicated in the 2019 college admissions scandal after disguising a US$500,000 bribe as a donation to the Key Worldwide Foundation. She was indicted on charges of fraud and bribery alongside her husband, designer Massimo Giannulli. Though she initially denied the allegations, Loughlin later pleaded guilty and was sentenced to two months in prison in 2020.

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O.J. Simpson -

O.J. Simpson was famously found innocent of the murder of his ex-wife Nicole Brown Simpson. However, 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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Fetty Wap -

Rapper Fetty Wap, real name Willie Junior Maxwell II, received a prison sentence of six years for drug charges. He was sentenced on May 24, 2023, after pleading guilty to his role in a drug trafficking conspiracy. It involved sending drugs like cocaine, heroin, fentanyl, and crack from the West Coast to the East Coast by mail or vehicle.

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Lindsay Lohan -

While struggling with addiction, Lindsay Lohan 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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50 Cent -

The rapper was put behind bars for six months when he was only 16 years old. He was sent to a correctional facility for minors after being convicted of several drug-related offenses. 

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Khloé Kardashian -

In 2008, Khloé Kardashian was sentenced to jail following probation violations of her 2007 DUI arrest. Despite being sentenced to 30 days, she was released just three hours into her incarceration due to prison overcrowding.

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Tommy Lee -

The Mötley Crüe drummer was sentenced to six months in prison in 1998. He was charged with the assault and battery of his wife, Pamela Anderson. He denied all the accusations. 

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Lil' Kim -

The rapper spent a year and a day in prison after she admitted to having lied to a grand jury about her friends' involvement in a 2001 shooting. She was also ordered to pay a US$50,000 fine.

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Zsa Zsa Gabor (1917-2016) -

In 1989, the Hungarian-American socialite and actress slapped a police officer who had pulled her over for a traffic violation in Beverly Hills. After refusing community service in a plea deal, Gabor was sentenced to three days in prison, which she completed. 

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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 1999 to 2001. 

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Christian Slater -

In 1997, Christian Slater was arrested after assaulting his then-girlfriend and 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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James Brown (1933-2006) -

Back in 1988, the legendary singer was on probation for drug offenses when he went on a crime spree that allegedly involved assault and battery. He refused to stop for police during a high-speed chase and was given six and a half years in prison, but got out after three.

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T.I. -

In 2010, rapper T.I. was sentenced to 11 months in prison for breaking federal probation after he was arrested in LA on drug charges. The year prior, he also served seven months in an Arkansas prison after being arrested for trying to buy unregistered guns and silencers from undercover federal agents.

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Todd and Julie Chrisley -

'Chrisley Knows Best' stars Todd and Julie Chrisley were sentenced to 12 and 7 years in federal prison, respectively, following their tax fraud convictions. They were found guilty in June 2022 of 12 counts, including wire fraud and conspiracy to commit bank fraud. 

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Ja Rule -

Often in trouble with the law, Ja Rule was sentenced to two years in prison for possession of an unauthorized gun in 2010. While incarcerated, he was sentenced to a further 28 months for not paying his taxes. 

Sources: (Redbook) (SheKnows) 

See also: The art of the con: history's most infamous scammers

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