20 Actors Who Spent Time Behind Bars

Some of Hollywood’s brightest stars have faced moments that dimmed their shine. From legal troubles to serious crimes, actors aren’t immune to the consequences of their actions, and many have spent time behind bars for reasons that range from minor slip-ups to shocking offenses.

I’ve put together a list of 20 actors who’ve served time in prison, exploring their stories and the roles that made them famous. Each entry looks at their crimes and the impact on their lives and careers, showing how even the most celebrated names can face real-world repercussions.

Robert Downey Jr.

Best known for playing Tony Stark in ‘Iron Man’ (2008) and the Avengers series (2012-2019), Robert Downey Jr. is a Hollywood icon with a turbulent past. His talent has earned him global fame, but his early years were marked by struggles that led to legal trouble.

In the late 1990s, Downey faced multiple arrests for drug-related charges, including possession of cocaine, heroin, and a firearm. After missing court-ordered drug tests, he was sentenced to three years in prison in 1999, serving nearly a year before early release. His journey to sobriety and a stellar comeback redefined his career.

Mark Wahlberg

Mark Wahlberg, celebrated for roles in ‘The Departed’ (2006) and ‘Ted’ (2012), started as a rapper before becoming a leading man. His early life, however, was far from glamorous, rooted in a rough Boston neighborhood.

At 16, Wahlberg was convicted of assault after attacking two Vietnamese men in an unprovoked incident, using racial slurs. Sentenced to two years, he served 45 days at Deer Island House of Correction. He later turned his life around, becoming a philanthropist and a respected actor.

Sean Penn

Sean Penn, an Oscar winner for ‘Mystic River’ (2003) and ‘Milk’ (2008), is known for intense performances and a fiery personality. His roles in ‘Dead Man Walking’ (1995) and ‘I Am Sam’ (2001) showcase his depth, but his temper led to trouble.

In 1987, while on probation for prior assaults, Penn punched an extra on the set of ‘Colors’ (1988). He was sentenced to 60 days in jail, serving 33. Despite these incidents, his career has remained strong, with continued critical acclaim.

Wesley Snipes

Wesley Snipes, the action star of ‘Blade’ (1998) and ‘The Expendables 3’ (2014), brought charisma to roles like the vampire hunter Blade. His off-screen choices, however, landed him in serious legal hot water.

Convicted in 2008 for failing to file federal tax returns, Snipes served three years in prison from 2010 to 2013. After his release, he returned to acting, reflecting on the value of time and freedom, and continued to take on new projects.

Tim Allen

Tim Allen, beloved for ‘Home Improvement’ (1991-1999) and voicing Buzz Lightyear in ‘Toy Story’ (1995), had a troubled past before fame. His comedic charm made him a household name, but his early years were rocky.

In 1978, Allen was arrested at a Michigan airport with over a pound of cocaine. Facing a possible life sentence, he took a plea deal, serving over two years in federal prison. Paroled in 1981, he rebuilt his life, becoming a comedy and acting star.

Christian Slater

Christian Slater, known for ‘Heathers’ (1988) and ‘Mr. Robot’ (2015-2019), has a knack for playing edgy characters. His intense on-screen presence mirrors a personal life that once veered into chaos.

In 1997, Slater served three months for assaulting his girlfriend while under the influence of drugs and alcohol. He’d also spent 10 days in jail in 1989 for drunk driving. These incidents didn’t derail his career, as he continued to land compelling roles.

Danny Trejo

Danny Trejo, the tough-guy actor in ‘Machete’ (2010) and ‘Sons of Anarchy’ (2008-2014), has a gritty backstory that shaped his iconic persona. His rugged roles often draw from his real-life experiences.

Trejo’s early life included drug dealing and arrests starting at age 10. He spent time in prison for robbery and drug offenses in the 1960s, with his longest stint at San Quentin. After turning his life around, he became an actor and advocate for recovery.

Lillo Brancato Jr.

Lillo Brancato Jr., recognized for ‘A Bronx Tale’ (1993) and ‘The Sopranos’ (1999-2007), showed promise as a young actor. His career took a dark turn due to personal struggles with addiction.

In 2005, Brancato was involved in a burglary that led to the death of an off-duty police officer. Convicted of second-degree murder, he served eight years in prison, released in 2013. He has since worked to rebuild his life and acting career.

Mike Tyson

Mike Tyson, a former boxing champion and actor in ‘The Hangover’ (2009), is known for his larger-than-life presence. His athletic fame transitioned into cameo roles, but his past includes serious legal issues.

In 1992, Tyson was convicted of raping an 18-year-old in an Indianapolis hotel room. Sentenced to six years, he served less than three in a federal facility. After release, he pursued acting and public appearances, maintaining a controversial profile.

Tommy Lee

Tommy Lee, Mötley Crüe’s drummer and actor in ‘The Dirt’ (2019), is a rock star with a wild reputation. His high-energy performances and personal life often made headlines for the wrong reasons.

In 1998, Lee served six months in prison for assaulting his then-wife, Pamela Anderson. The incident stemmed from a domestic dispute, adding to his legal troubles. He later returned to music and acting, keeping his rock persona intact.

Amy Locane

Amy Locane, known for ‘Cry-Baby’ (1990) and ‘Melrose Place’ (1992-1999), was a rising star in the early 1990s. Her career was overshadowed by a tragic event that changed her life.

In 2010, Locane was convicted of vehicular homicide after a drunk-driving crash killed a 60-year-old woman. Initially sentenced to three years, she was re-sentenced to eight years in 2020 due to a lenient first ruling. She served her time and has since kept a low profile.

Michael Jace

Michael Jace, recognized for ‘The Shield’ (2002-2008) and ‘Forrest Gump’ (1994), played compelling roles as a character actor. His life took a tragic turn with a crime that shocked fans.

In 2014, Jace shot and killed his wife in their Los Angeles home, confessing to police. Convicted of second-degree murder, he was sentenced to 40 years in prison. The case ended his acting career, leaving a grim legacy.

Robert Mitchum

Robert Mitchum, a film noir legend in ‘Cape Fear’ (1962) and ‘The Night of the Hunter’ (1955), was a Hollywood icon with a rebellious streak. His laid-back style masked a turbulent early life.

In 1949, Mitchum served a brief prison term for marijuana possession, which only enhanced his ‘bad boy’ image. The stint didn’t slow his career, as he became a leading man in westerns and dramas, beloved by audiences.

Stephen Fry

Stephen Fry, known for ‘Blackadder’ (1983-1989) and ‘V for Vendetta’ (2005), is a versatile actor and writer. His wit and charm define his career, but his youth included a misstep.

As a teenager, Fry spent three months in Pucklechurch prison for credit card fraud. He turned his life around, attending Cambridge and becoming a celebrated figure in entertainment, known for his intelligence and humor.

Bill Cosby

Bill Cosby, star of ‘The Cosby Show’ (1984-1992), was once America’s beloved TV dad. His comedic legacy was shattered by allegations that led to a high-profile conviction.

In 2018, Cosby was sentenced to three to ten years for sexually assaulting a woman in 2004. He served nearly three years before his conviction was overturned in 2021 due to a legal agreement. His case remains controversial.

Felicity Huffman

Felicity Huffman, known for ‘Desperate Housewives’ (2004-2012) and ‘Transamerica’ (2005), is an Emmy-winning actress. Her involvement in a scandal surprised many fans.

In 2019, Huffman pleaded guilty to fraud in the college admissions scandal, paying $15,000 to boost her daughter’s SAT scores. She served 11 days of a 14-day sentence, expressing regret and focusing on rebuilding her reputation.

Lori Loughlin

Lori Loughlin, beloved for ‘Full House’ (1987-1995), faced a public fall from grace. Her wholesome image as Aunt Becky contrasted with a serious legal issue.

Also caught in the 2019 college admissions scandal, Loughlin pleaded guilty to conspiracy for paying $500,000 to secure her daughters’ college admissions. She served two months in prison, later returning to acting with a quieter public presence.

Jamie Waylett

Jamie Waylett, known as Vincent Crabbe in the ‘Harry Potter’ series (2001-2011), played a memorable bully. His off-screen actions led to a dramatic career halt.

In 2011, Waylett was convicted of violent disorder during the London riots, receiving a two-year sentence. He also faced charges for growing cannabis. His time in prison marked the end of his acting career.

Lil’ Kim

Lil’ Kim, a rapper and actress in ‘She’s All That’ (1999), is a music icon with a bold persona. Her legal troubles stemmed from loyalty to friends.

In 2005, she was sentenced to a year in prison for lying to a federal grand jury about a 2001 shooting involving her entourage. Released after 10 months, she quickly returned to music, earning Grammy nominations.

Danny Masterson

Danny Masterson, known for ‘That ‘70s Show’ (1998-2006), was a familiar face in sitcoms. His career was derailed by serious allegations that led to a long sentence.

In 2023, Masterson was convicted of raping two women between 2001 and 2003. Sentenced to 30 years to life, he’s eligible for parole after 20 years. The case ended his acting career amid public scrutiny.

Which actor’s story surprised you most, or did I miss anyone with a notable prison stint? Share your thoughts in the comments!