Stars Behind Bars: 25 Celebrities Who Went to Prison
Robert Downey Jr.
Imagine Tony Stark behind bars, only without the gadgets! Before Iron Man saved the world, Robert Downey Jr. was busy trying to save himself from his own bad habits. In the ’90s, Downey’s talent on screen was rivaled only by his run-ins with the law. A string of drug arrests finally caught up with him in 1999, when a judge sent him to prison for skipping probation.
Tim Allen
Long before he was the goofy dad in 'Home Improvement' or the voice of Buzz Lightyear, Tim Allen’s “to infinity and beyond” looked more like “to prison and back.” In 1978, Allen was busted at a Michigan airport with over a pound of cocaine. He has often joked about the experience, saying prison forced him to rethink everything.
Wesley Snipes
Wesley Snipes could take down vampires as Blade, but he couldn’t escape the IRS. In the 2000s, the action star was charged with failing to file tax returns, which was severe enough to earn him three years behind bars. By 2010, Snipes was no longer fighting demons on screen but instead adjusting to life in a Pennsylvania prison. Fans were stunned: their martial arts hero now had a real-life villain named “Tax Evasion.”
Paris Hilton
Paris Hilton turned jail into another episode of her reality show. In 2007, after violating probation for a DUI, she was sentenced to 45 days behind bars. She served about 23 days, complete with paparazzi helicopters circling the prison gates. At first, Paris tried to swap her cell for house arrest, but the judge wasn’t having it. Inmates called her “Princess” while the world debated if she was getting special treatment.
Mark Wahlberg
Before he became Marky Mark turned Oscar nominee, Wahlberg was a 16-year-old street tough in Boston. In 1988, he attacked two Vietnamese men in a racially charged incident that landed him a two-year sentence. He served 45 days before release. Wahlberg has since admitted regret, and the shadow of that teenage mistake still follows him. Yet Hollywood loves a redemption story, and Wahlberg turned his life around.
Michelle Rodriguez
Michelle Rodriguez doesn’t just play rebels on screen; she has lived the role off-screen too. Known for 'Fast & Furious,' Rodriguez violated probation from earlier DUI cases and was sentenced in 2007 to 180 days in jail. Thanks to overcrowding, she served less, but it still made headlines.
Kiefer Sutherland
You’d think Jack Bauer could talk his way out of anything...except DUIs. In 2007, Kiefer Sutherland was sentenced to 48 days in jail after yet another drunk-driving incident violated his probation. Instead of fighting terrorists on '24,' Sutherland was eating prison meals and serving time at Glendale City Jail. He even scheduled his sentence around filming, proving that the show—and the paycheck—must go on.
Danny Trejo
Before Danny Trejo was Hollywood’s go-to tough guy, he bounced in and out of California prisons for robbery and drug-related charges, including time at the notorious San Quentin. He discovered boxing while inside, which changed his life. Trejo often says prison was the crucible that turned him from a criminal into a cult icon.
Tom Sizemore
Tom Sizemore’s life was a mix of Hollywood highs and devastating lows. Known for 'Saving Private Ryan' and 'Heat,' he battled drug addiction that repeatedly landed him in trouble. In 2007, after violating probation in a drug case, Sizemore was sentenced to 16 months in prison, and his mugshots and public meltdowns made headlines. Though he continued to work sporadically, his prison time became part of his infamous reputation.
Allison Mack
'Smallville' star Allison Mack shocked the world when she was revealed as a key figure in NXIVM, the so-called self-help group exposed as a sex cult. In 2019, she pleaded guilty to racketeering and conspiracy charges and, in 2021, was sentenced to three years in prison. She served a little over two years before her release in 2023. Mack’s downfall remains one of Hollywood’s most bizarre scandals.
Bill Cosby
Once America’s TV dad, Bill Cosby became one of the biggest downfalls in entertainment history. In 2018, he was convicted of aggravated indecent assault and sentenced to up to ten years in prison. He served nearly three years before the conviction was overturned on a technicality.
Harvey Weinstein
If Hollywood has a villain, Harvey Weinstein is it. In 2020, the powerful producer was convicted of sexual assault in New York, sentenced to 23 years, and later hit with another 16-year sentence in Los Angeles. Though parts of his case have been overturned, Weinstein remains behind bars. For decades, he controlled careers, but prison stripped away his power.
Mike Tyson
In 1992, boxing champ Mike Tyson’s life outside the ring crashed when he was convicted of rape in Indiana. He was sentenced to six years but served just under three before being paroled. For fans, it was shocking because the “baddest man on the planet” was now behind bars. Tyson was released in 1995, but prison had altered both his career trajectory and public image.
Felicity Huffman
Felicity Huffman shocked fans in 2019 when she was caught in the infamous college admissions scandal. She admitted to paying $15,000 to inflate her daughter’s SAT scores, and the courts didn’t let it slide. Huffman was sentenced to 14 days in federal prison, of which she served 11.
Lori Loughlin
Aunt Becky in 'Full House' always seemed perfect, which made Lori Loughlin’s downfall in the college admissions scandal even juicier. In 2020, she admitted to paying $500,000 to get her daughters into USC as fake crew recruits. The result was a two-month prison sentence, which she served in late 2020. Loughlin has tried to rebuild her reputation since, but her prison story remains one of Hollywood’s most unexpected scandals.
Stephen Fry
Before he was Britain’s beloved wit, Stephen Fry was a troubled teen with a stolen credit card habit. In 1975, at just 17, Fry spent several months in prison after being caught for fraud. It’s almost impossible to picture the charming host of QI pacing a prison cell, but Fry has spoken openly about how the experience changed him. He went from troubled youth to Cambridge scholar to national treasure.
Boy George
Culture Club frontman Boy George found himself on the wrong side of the law in 2009 when he was convicted of falsely imprisoning a male escort. The singer was sentenced to 15 months, serving about four. Once free, he went back to performing and hasn’t given up on it since.
Christian Slater
Christian Slater was the bad boy of the '90s. In 1997, he was arrested after a violent outburst involving his then-girlfriend and a police officer while under the influence. The court sentenced him to three months in jail, though he served about 59 days. At the time, Slater’s career looked like it might not recover from the chaos. But he bounced back.
Sophia Loren
She’s one of the most glamorous women in film history, but even Sophia Loren wasn’t immune to prison bars. In 1982, Loren served 17 days of a 30-day sentence in Italy over a tax dispute. She handled it with grace and treated it like a plot twist in her legendary career. Later legal rulings even supported her side of the case, but the short jail stay became part of her story.
Robert Mitchum
In 1948, Hollywood bad boy Robert Mitchum was busted for marijuana possession. Convicted in early 1949, he served about two months in county jail and on a prison farm. Instead of letting it tank his career, the arrest only added fuel to the “bad boy” image that made him irresistible.
Martha Stewart
Leave it to Martha Stewart to make even prison look like a lifestyle brand. In 2004, she was convicted of conspiracy and lying to investigators about a stock trade. She spent five months at FPC Alderson, followed by home confinement. America’s queen of home décor went from baking pies to living in a prison dorm.
Teresa Giudice
Reality TV fans got their ultimate shock when 'Real Housewives of New Jersey' star Teresa Giudice went behind bars. In 2014, she was sentenced to 15 months for fraud, serving 11 before heading home. However, Teresa turned her post-prison life into a storyline and even wrote a memoir about the experience. Her time behind bars didn’t dim her reality TV crown; if anything, it made her even more infamous.
O.J. Simpson
O.J. Simpson’s infamous murder trial may have ended in acquittal, but his later downfall was straight out of a made-for-TV movie. In 2008, Simpson was convicted of armed robbery and kidnapping after a botched attempt to reclaim sports memorabilia in a Las Vegas hotel. Ultimately, he ended up serving nine years of a possible 33-year sentence.
Leslie Grantham
Long before he was “Dirty Den” on EastEnders, Leslie Grantham had his own real-life drama. Back in 1966, while serving as a soldier in Germany, he was convicted of killing a taxi driver. Grantham spent about ten years in prison before being released in 1977. Instead of fading away, he turned his life around, trained as an actor, and eventually landed one of the most iconic soap roles on British TV.
George Michael
Pop icon George Michael was no stranger to headlines, but in 2010, he made the front page for the wrong reasons. After crashing his car while under the influence of drugs, he was sentenced to eight weeks in prison. He served about four weeks at Highpoint Prison, trading concert arenas for cell blocks. Fans were stunned, though his time inside didn’t dull his shine.
