By Jessica Wedemeyer
7:51pm PDT, Apr 20, 2023
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It may seem like celebrities live in a different world, but they still have to answer to the law! We've rounded up the stars who've served time behind bars over the years…
Robert Downey Jr. hasn't always acted like a superhero. The A-lister spent time behind bars in 1997 and 1999 for several drug-related run-ins with the law. In June 1996, police found crack, cocaine, heroin and a pistol in the actor's car after he was pulled over for speeding near his Malibu home. He was charged with DWI, possession of a concealed weapon and possession of controlled substances. That same year, he passed out in a neighbor's home after breaking in while under the influence. He was put on probation for his crimes — but landed in jail for four months in 1997 after he missed a drug test. He spent almost a year behind bars in 1999 when he missed yet another drug test.
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Kiefer Sutherland spent 48 days behind bars in late 2007 and early 2008 after he was arrested for DUI in September 2007. It was his fourth DUI-related arrest and it violated the terms of his probation stemming from a November 2004 DUI conviction. (The "24" star was also charged with DUI in 1989 and 1993.) The actor spent his birthday, Christmas and New Year's Eve in the slammer as a result of his status as a repeat offender.
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More than a decade before he became a household name thanks to his role as Tim "The Tool Man" Taylor on "Home Improvement," Tim Allen spent more than two years in prison. In October 1978, he was caught attempting to transport 650 grams of cocaine through a Michigan airport — a crime for which he could have been sentenced to life in prison. Instead, he pleaded guilty to drug trafficking charges and revealed the identities of 21 of his associates to authorities. In exchange, he received a reduced sentence.
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For his part in the 2019 college admissions scandal, Lori Loughlin's fashion designer husband, Mossimo Giannulli, got a five-month sentence. He reported to prison in November 2020 and was released in April 2021.
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Paul McCartney might not have been officially charged with a crime, but he still spent nine days in a Japanese jail in January 1980 after customs officials at Narita International Airport found eight ounces of cannabis in his luggage. The former Beatle had just touched down in Tokyo for a tour of Japan with his band Wings when he was arrested and jailed. After nine days, the superstar was released and deported, effectively avoiding the usual penalty for his crime: seven years of hard labor.
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In October 2014, Teresa Giudice was sentenced to 15 months behind bars for fraud. (She and her husband, Joe Giudice, were charged with misrepresenting their wealth while taking out loans and later lying about their improved financial situation while filing for bankruptcy.) The longtime star of "The Real Housewives of New Jersey" reported to a Connecticut prison in January 2015 and was released 11 months later — two days before Christmas 2015. As for her then-husband…
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In October 2014, Teresa Giudice's then-husband, Joe Giudice, was sentenced to 41 months behind bars for fraud. He reported to a New Jersey prison in March 2016 — three months after his missus returned home from her own prison sentence. He was released in March 2019 but didn't exactly go free. In late 2018, a judge ruled that the father of four — who never obtained American citizenship even though he's lived in the United States since he was a baby — should be deported to his native Italy following his prison term. When his time was up, he was remanded to ICE custody. He fought his deportation for months but ultimately moved to Italy in October 2019. He and Teresa have since ended their marriage.
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Another reality star who spent time behind bars for bankruptcy fraud? Abby Lee Miller! The "Dance Moms" personality — who reportedly hid $755,000 in income from the government — served eight months of a one-year sentence in a Southern California prison in late 2017 and early 2018. She then spent two months in a halfway house.
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Sean Penn was sentenced to 60 days in jail back in 1987 thanks to a reckless driving charge and punching an extra on the set of his film "Colors" — the violations occurred while he was already on probation. He'd previously pleaded no contest to punching someone at a nightclub earlier that year after he thought the man kissed his then-wife, Madonna. He ended up serving 33 days of his sentence.
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If you want to live La Vida Lohan, you'd better be prepared to spend some time in the slammer. Lindsay Lohan ended up behind bars for 13 days in August 2010 after she accidentally triggered the alcohol-monitoring device she was ordered to wear as part of her probation following her second DUI conviction. She wound up behind bars again two months later — but this time for less than a day — when she failed a drug test. She spent a few hours in jail again in April 2011 and November 2011 for violating the terms of her probation.
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Danny Trejo spent most of his early adult life in and out of the penal system, passing time at San Quentin, Folsom, Soledad, Vacaville, Susanville and Sierra prisons over the course of his illustrious criminal career — which isn't too surprising considering he was first arrested for assault and battery at age 10. The "Machete" star eventually graduated to armed robbery and drug dealing. He even faced the death penalty at one point!
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Paris Hilton ended up behind bars for 23 days in May 2007 after she violated the terms of her probation stemming from a September 2006 DUI conviction by repeatedly driving with a suspended license. "It was a horrible experience, but at the same time, it's something that made me a stronger person. I know that I can get through anything and do anything now that I went through that," she later told People magazine.
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In the summer of 2019, A$AP Rocky spent a month in a Swedish jail as authorities investigated his part in a physical altercation with a man on the streets of Stockholm. The rapper, who claimed he was simply defending himself, was later found guilty of assault, though he faced no additional jail time.
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Martha Stewart spent five months behind bars in a West Virginia women's prison and five months under house arrest from October 2004 to August 2005 after she was found guilty of conspiracy, making false statements and obstruction of justice relating to the 2001 sale of $230,000 in ImClone Systems Inc. stock. (Martha's company sold its shares of ImClone the day before the FDA decided not to approve the company's new cancer drug, and the SEC accused Martha and her business partners of insider trading.)
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In November 2017, a judge sentenced Meek Mill to two to four years in prison for violating the terms of his probation stemming from a 2007 arrest on drug and gun charges when he was 19. The violations? Popping wheelies on a dirt bike and scuffling with two employees badgering him for a photo at an airport in St. Louis. The rapper served five months of his sentence until a Pennsylvania appeals court secured his early release in April 2018. He's since become a prominent advocate for criminal justice reform.
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In 2019, Mike "The Situation" Sorrentino spent eight months behind bars in a New York federal prison for tax evasion. The "Jersey Shore" star and his brother, Marc, were indicted twice: first in 2014 and then again in 2017 for conspiring to defraud the United States government by failing to pay taxes on his income.
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Back when Mark Wahlberg was Marky Mark, he was a very naughty boy with an adult-sized rap sheet. "I wanted to be the cool guy in the neighborhood, to be what I thought was a bada**," the Boston native told NPR of his criminal behavior, which included stealing cars, selling pot and multiple assault charges. In 1998, he assaulted two Vietnamese men, leaving one partially blind. He pleaded guilty to assault and was sentenced to two years in prison, though he served just 45 days of his term.
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Despite his impressive rap sheet — which includes various arrests for drug, assault and weapons charges — 50 Cent has only been to jail once. The rapper served six months in a youth "shock incarceration" boot camp program after he was arrested for his role in selling cocaine to an undercover police officer. (He managed to avoid a three-to-nine-year prison sentence!)
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In 1989, Christian Slater spent 10 days behind bars after he pleaded no contest to charges of drunk driving and evading arrest. (He led deputies on a car chase after they attempted to pull him over for speeding, crashed into a telephone pole and then resisted arrest by kicking a police officer in the head.) It was his second drunk driving charge in two years. The actor returned to jail for nearly two months in early 1998 after he was charged with assaulting his girlfriend and a police officer while on a cocaine- and booze-fueled bender.
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Michelle Rodriguez spent two days behind bars in 2005 and 17 days behind bars in late 2007 and early 2008 after she got a little too fast and furious IRL. Michelle landed in a Honolulu jail in December 2005 after she was arrested for DUI. Six months later, she spent a few hours in a Los Angeles jail after she violated her probation. The "Fast & Furious" franchise star then went to prison in December 2007 when she violated her probation yet again by failing to provide proof that she had completed her community service and by triggering her court-ordered alcohol-monitoring device on three separate occasions.
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Snoop Dogg spent time in jail off and on during the early '90s as a result of his illegal pre-fame activity. Specifically, the rapper landed in the slammer for felony cocaine possession in 1990 shortly after he graduated from high school. His rap sheet also includes several charges for possession of illegal firearms and many, many, many charges of illegal possession of marijuana.
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T.I. was arrested in 2007 for attempting to purchase unregistered machine guns and silencers. As a result, the rapper spent seven months at an Arkansas prison in 2009 and then three months at Atlanta's Dismas Charities halfway house. He was still under probation in September 2010 when he and his wife, Tiny Harris, were arrested on drug possession charges in West Hollywood. The rapper returned to federal prison for 10 months in 2010 and 2011 for violating his parole.
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Lil Wayne spent nearly eight months at New York's Rikers Island jail in 2010 after he pleaded guilty to second-degree weapons possession: Police found a handgun on his tour bus in July 2007, and while the rapper initially denied the firearm was his, authorities used DNA evidence to link it to him.
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Chris Klein spent four days behind bars in 2010 after he was charged with his second DUI. (He earned his first DUI in February 2005.) As a repeat offender, the "American Pie" actor faced a mandatory minimum sentence of four days in jail.
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In early 2009, Boy George served four months of a 15-month sentence at prisons in London and Suffolk, England. The Culture Club singer was found guilty of gratuitous violence for assaulting and imprisoning Norwegian male escort Audun Carlsen — whom he reportedly handcuffed and beat with a chain — in his London flat in 2007. Following his early release, the Brit was placed on house arrest for 90 days.
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Lil' Kim spent 10 months behind bars in 2005 and 2006 after she was convicted of perjury. The rapper lied to a federal grand jury to protect members of her entourage who were involved in a 2001 gun battle opposite rival rap group Capone-N-Noreaga outside a Manhattan radio station. "I testified falsely in front of a grand jury and thought it was the right thing to do," Kim said in court. "Now I realize it was wrong."
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Wesley Snipes served two and a half years of a three-year sentence at McKean Federal Correctional Institution in Lewis Run, Pennsylvania. His crime? The actor failed to pay taxes on more than $38 million he earned between 1999 and 2006. After more than two years of unsuccessfully attempting to appeal his conviction, the "Blade" star finally began his term in December 2010. He was released to his New York home in April 2013 to complete the remainder of his sentence. "I came out a clearer person," he told The Guardian in 2020. "Clearer on my values, clearer on my purpose, clearer about my relationship with my ancestors and the great god and the great goddess above, and clearer on what I was going to do once I had my freedom back." He added, "The biggest thing I got from it was learning the value of time and how we often squander it … I understand that very clearly now, having been away from my family and loved ones two and a half years."
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In 2013, Lauryn Hill spent three months in a Connecticut prison for failing to pay federal income taxes on $1.8 million she earned from 2005 to 2007.
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In 2011, Vince Neil spent 10 days on lockdown at Clark County Detention Center in Las Vegas after he pleaded guilty to drunk driving charges stemming from a June 2010 DUI arrest. The rocker also spent 15 days under house arrest. But it wasn't the Mötley Crüe singer's first time behind bars. In 1986, he spent 20 days in the slammer for drunk driving and vehicular manslaughter: The intoxicated rocker was responsible for the car crash that claimed the life of Hanoi Rocks drummer Nicholas "Razzle" Dingley.
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Remy Ma spent six years of her life — from 2008 to 2014 — in a New York prison after she was convicted of assault for shooting a member of her entourage in 2007. The rapper — who reportedly shot a close female friend twice after accusing her of stealing $2,000 — was sentenced to eight years behind bars but scored an early release.
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Unlike a lot of celebs on this list, Ja Rule got time added to his prison sentence! The rapper first received a sentence of two years 2011 — the result of 2007 charges for unauthorized gun possession. He received an additional 28 months for failing to pay more than $1 million in taxes but was able to serve both sentences concurrently and was released in May 2013 after doing a little less than two years behind bars.
