Behind Bars: When Hollywood Stars Took a Detour to Jail
Even Hollywood’s brightest names sometimes trade red carpets for orange jumpsuits. While some arrests were minor run-ins with the law, others left lasting marks on their careers. From shocking DUIs to wild brawls, these actors prove that fame doesn’t always guarantee freedom. Let’s look at the stories of actors who actually spent time in jail—and how it impacted their lives on and off screen.
Robert Downey Jr.
Before becoming Marvel’s beloved Iron Man, Robert Downey Jr. had a rough patch (to put it lightly) in the 1990s. He was arrested multiple times for substance possession and even spent nearly a year in prison.
Hollywood had practically written him off, but Downey pulled off one of the greatest comebacks ever, eventually headlining Iron Man and Sherlock Holmes.
Paramount Pictures, Iron Man 2 (2010)
Lindsay Lohan
Once a Disney darling thanks to The Parent Trap and Mean Girls, Lindsay Lohan’s career hit turbulence with a series of arrests in the mid-2000s. She served brief stints in county jail for DUI and probation violations. Though her time behind bars was short, it became one of the most talked-about celebrity meltdowns of the era. These days, she’s making a quieter comeback with new projects—and fewer court dates.
Paramount Pictures, Mean Girls (2004)
Mark Wahlberg
Before his Hollywood success in Boogie Nights and The Departed, Mark Wahlberg had a much darker past. As a teenager, he was arrested for a violent assault and served 45 days in jail. Wahlberg has spoken openly about his troubled youth and how it fueled his drive to turn his life around. Now a top-paid actor and producer, he’s living proof of how dramatically someone’s path can change.
Warner Bros. Pictures, The Departed (2006)
Tim Allen
Long before becoming the voice of Buzz Lightyear in Toy Story, Tim Allen was arrested in 1978 for attempting to transport controlled substances. He ended up serving over two years in federal prison. Surprisingly, Allen later built a hugely successful career in comedy and acting, starring in Home Improvement and The Santa Clause. His prison time could have ended everything—but instead, it became a hidden chapter in his redemption arc.
Walt Disney Pictures, The Santa Clause (1994)
Wesley Snipes
Known for Blade and White Men Can’t Jump, Wesley Snipes faced legal trouble that didn’t involve stunts or vampires. In 2008, he was convicted of tax evasion and served nearly three years in prison. Despite the setback, Snipes returned to acting with renewed energy, even making fun of his situation in interviews. His career never fully disappeared—if anything, it added another layer to his larger-than-life Hollywood persona.
Mickey Rourke
Mickey Rourke has always been a Hollywood wild card, both onscreen and off. In 1994, he spent time in jail after being arrested for domestic disputes and brawling. His bad-boy reputation only grew from there, but it didn’t stop him from reviving his career with Sin City and The Wrestler. Fans know that with Rourke, chaos is never too far behind the camera.
Fox Searchlight Pictures, The Wrestler (2008)
Martin Sheen
Not all celebrity arrests are about parties or fights—sometimes it’s about activism. Martin Sheen, star of The West Wing and Apocalypse Now, has been arrested over 60 times for civil disobedience at protests. While many of these landed him in holding cells rather than long-term jail, he’s spent plenty of hours behind bars for causes he believes in. For Sheen, jail was never a scandal—it was a statement.
United Artists, Apocalypse Now (1979)
Kiefer Sutherland
Best known for playing Jack Bauer on 24, Kiefer Sutherland has had his share of off-screen drama. In 2007, he served 48 days in jail after multiple DUI offenses. Interestingly, Sutherland was still filming 24 at the time, and his prison stint was scheduled around his work commitments. Fans joked that Bauer could break out of any cell—but Sutherland took his punishment seriously and quietly served his time.
20th Television, 24 (2001–2010)
Christian Slater
A breakout star in Heathers and True Romance, Christian Slater’s rebellious streak didn’t stop at the movies. In the late ’90s, he served time in jail for assault and drunk driving. His stay behind bars was short, but it added to his “bad boy” image that both haunted and fueled his career. Slater later reinvented himself with projects like Mr. Robot, proving that second acts in Hollywood are possible.
Universal Content Productions, Mr. Robot (2015–2019)
Sean Penn
Famous for Fast Times at Ridgemont High and Mystic River, Sean Penn was notorious in the ’80s for his fiery temper. In 1987, he spent over a month in jail after an assault on a photographer while still married to Madonna. Penn has since channeled his intensity into acclaimed performances and humanitarian work, but back then, his time behind bars made him one of Hollywood’s most unpredictable stars.
Warner Bros. Pictures, Mystic River (2003)
Danny Trejo
Before becoming the go-to tough guy in Machete and From Dusk Till Dawn, Danny Trejo spent years in prison during his youth. Arrested multiple times, he served extended time for robbery and related offenses. It was in prison that he turned his life around, getting clean and eventually becoming a boxing champion behind bars. Today, he’s one of Hollywood’s favorite redemption stories—proof that a rough start doesn’t dictate the finish.
Miramax Films, From Dusk Till Dawn (1996)
Shia LaBeouf
Shia LaBeouf’s career has seemingly had as many twists off-screen as it has on. Known for Transformers and Honey Boy, he’s been arrested multiple times for disorderly conduct and did spend time in jail. While polarizing, his jail stints have become part of his complicated narrative as one of Hollywood’s most unpredictable actors.
Paramount Pictures, Transformers (2007)
Charlie Sheen
At the height of his Two and a Half Men fame, Charlie Sheen’s personal life was just as headline-grabbing as his career (if not moreso). In 2009, he spent time in an Aspen jail for domestic violence charges. Sheen’s stint behind bars only added to his “bad boy” persona, fueling his notorious “winning” era soon after.
Warner Bros. Television, Two and a Half Men (2003–2015)
Josh Brolin
Before his Oscar-nominated performances in Milk and villainous turn as Thanos in Avengers: Infinity War, Josh Brolin had a rocky past. In the early 2000s, he was arrested after a domestic dispute and briefly jailed. Though the incident made headlines, it didn’t derail his career for long. Brolin has since become one of Hollywood’s most respected actors, proving that mistakes don’t always define the man.
Josh Brolin on Playing Thanos in the MCU, The Howard Stern Show
Russell Brand
Comedian and actor Russell Brand, known for his roles in Forgetting Sarah Marshall and Get Him to the Greek, had several run-ins with the law back in the early 2000s.
Brand was arrested multiple times for public disturbances and spent multiple short stints in jail. He later turned his life around, becoming a best-selling author and activist, with his brushes with jail only added to his eccentric, wild reputation in Hollywood.
Universal Pictures, Get Him to the Greek (2010)
Danny Bonaduce
A child star on The Partridge Family, Danny Bonaduce’s adult life was filled with legal troubles. He was arrested multiple times and even spent time in jail for assault and other charges. Bonaduce’s off-screen drama overshadowed his early fame, but he later reinvented himself as a radio host and reality TV personality.
From Child Star to Comeback King: Danny Bonaduce Opens Up, Eric Metaxas
Nick Nolte
Nick Nolte’s 2002 mugshot is one of the most infamous in Hollywood history. The 48 Hrs. and The Prince of Tides star was arrested for DUI and spent time in county jail. His disheveled photo went viral before viral was even a thing. Nolte has since continued acting, but that wild mugshot and jail stint remain unforgettable parts of his public image.
Paramount Pictures, 48 Hrs. (1982)
Stephen Fry
Before he was a beloved British actor and comedian, Stephen Fry actually served time for credit card fraud as a teenager (At just 17, he was sentenced to three months in prison). Fry has openly spoken about how the experience shaped him, ultimately pushing him toward writing, comedy, and acting.
Randy Quaid
Known for his roles in Independence Day and National Lampoon’s Vacation, Randy Quaid’s later life has been more infamous than famous. He’s been arrested multiple times for burglary and fraud-related issues, spending time in jail both in the U.S. and Canada. His bizarre behavior and conspiracy-laden rants only added to the drama. Once a respected actor, Quaid is now remembered as much for his arrests as his roles.
20th Century Fox, Independence Day (1996)
Amanda Bynes
A Nickelodeon favorite and star of She’s the Man, Amanda Bynes had a highly publicized downfall in the 2010s. She was arrested for DUI and other incidents, spending brief time in jail before entering rehab programs. While her troubles sidelined her career, fans still root for her recovery. Her time behind bars became a symbol of how brutal the spotlight can be for young stars.
Paramount Pictures, She’s the Man (2006)
Michelle Rodriguez
The Fast & Furious actress has always embraced her tough-girl image, both on and off screen. Rodriguez was sentenced to jail in 2006 after violating probation for DUI-related offenses. Though her time behind bars was short, it reinforced her reputation as Hollywood’s rebel. Despite setbacks, Rodriguez remains a fan favorite, continuing to play fierce, no-nonsense roles that audiences love.
Universal Pictures, Furious 7 (2015)
Lauryn Hill
Best known as a singer, Lauryn Hill also starred in Sister Act 2 before focusing on music. In 2013, she served three months in prison for tax evasion. While her acting career took a backseat, her jail stint made headlines worldwide. Hill remains a cultural icon, and her time behind bars is often seen as part of her larger struggle with fame and the industry’s pressures.
Tom Sizemore
Known for intense roles in Saving Private Ryan and Heat, Tom Sizemore had numerous legal troubles. He served time in jail for assault and probation violations, struggles that frequently made headlines. While his talent was undeniable, his jail stints and personal battles often overshadowed his career. Sizemore continued acting but never quite reached the heights many thought he was destined for.
Paramount Pictures, Saving Private Ryan (1998)
Matthew Newton
An Australian actor and director, Matthew Newton was arrested multiple times for assault and other charges. He served jail time in his home country, with his off-screen behavior limiting his opportunities in Hollywood. Despite talent behind the camera, his reputation was marred by these legal issues. Newton’s story highlights how quickly a career can unravel when personal troubles spill into the public eye.
EXTRA MINUTES - MATTHEW NEWTON (Reporter discussion), 60 Minutes Australia
Eric Roberts
Julia Roberts’ brother and star of Runaway Train, Eric Roberts spent time in jail in the 1980s after being arrested for substance-related charges and resisting arrest. Though his stint was short, it added to his reputation as a Hollywood wild child. Roberts has since built a long career in film and TV, proving resilience runs in the family—even if his path was more chaotic than his sister’s.
Ron Galella, Ltd., Getty Images
Shelley Malil
Best remembered for his role in The 40-Year-Old Virgin, Shelley Malil’s career ended in tragedy when he was convicted of attempted murder in 2010. He was sentenced to life in prison, though he was later granted parole after serving several years. Unlike others on this list, Malil’s time in jail effectively ended his Hollywood career, leaving a dark stain on his legacy.
Edward Furlong
The child star of Terminator 2: Judgment Day struggled as an adult with numerous arrests. He spent time in jail for probation violations and domestic disputes. Once seen as a rising star, Furlong’s legal troubles derailed what could have been a major career. While he still acts occasionally, his jail stints remain a reminder of how fame at a young age can sometimes go off the rails.
TriStar Pictures, Terminator 2: Judgment Day (1991)
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