20 Actors Who Spent Time Behind Bars

A number of prominent celebrities in Hollywood have experienced periods where their luster faded. Ranging from legal issues to heinous crimes, these stars aren’t exempt from the repercussions of their decisions, and several have served time in prison due to various infractions, some being relatively minor mishaps while others were startling transgressions.

I compiled a collection of 20 actors who have experienced imprisonment, delving into their individual tales and the roles that catapulted them to fame. Each account examines their crimes, the subsequent effects on their lives and professions, and underscores how even prominent figures can encounter genuine consequences in the real world.

Robert Downey Jr.

Known for portraying Tony Stark in ‘Iron Man’ (2008) and the Avengers series (2012-2019), Robert Downey Jr. is a well-recognized figure in Hollywood, who has had a challenging past. Despite his current success, which has garnered him international acclaim, his early life was filled with struggles that eventually resulted in legal issues.

In the late ’90s, Downey encountered several arrests due to drug offenses such as cocaine, heroin possession, and carrying a firearm. He missed mandatory drug tests which led to a three-year prison sentence in 1999. He served almost a year before an early release. His struggle for sobriety and successful comeback significantly reshaped his career path.

Mark Wahlberg

Mark Wahlberg, renowned for his performances in ‘The Departed’ (2006) and ‘Ted’ (2012), actually began his career as a rapper. Before reaching leading man status, though, his early life was marked by the gritty streets of Boston.

When he was sixteen, Wahlberg got convicted for assaulting two Vietnamese men in an unexpected attack, using offensive racial language. He was given a sentence of two years but only served 45 days at Deer Island House of Correction. Later on, he transformed his life, becoming a well-respected actor and philanthropist.

Sean Penn

Known for his passionate portrayals and fiery disposition, Sean Penn, who won Oscars for ‘Mystic River’ (2003) and ‘Milk’ (2008), has left an indelible mark in cinema. His roles in ‘Dead Man Walking’ (1995) and ‘I Am Sam’ (2001) highlight his acting range, although his temperament sometimes caused complications.

In the year 1987, during a period of probation for previous assault charges, Penn found himself involved in another altercation on the set of ‘Colors’ (1988). As a result, he was given a 60-day prison sentence, serving 33 days. Remarkably, his acting career has persisted, earning him continued praise from critics.

Wesley Snipes

As a huge fan, I can’t help but admire Wesley Snipes and his electrifying portrayal of characters such as the vampire hunter Blade in ‘Blade’ (1998) and ‘The Expendables 3’ (2014). Off-screen, however, his choices led him into some very challenging legal situations.

In 2008, Snipes was found guilty for not submitting federal tax returns, which led him to serve a prison sentence from 2010 to 2013. Upon his release, he resumed acting, appreciating the importance of time and liberty, and went on to accept more roles in various projects.

Tim Allen

Tim Allen, known for his roles in ‘Home Improvement’ (1991-1999) and as the voice of Buzz Lightyear in ‘Toy Story’ (1995), had a challenging past that preceded his stardom. Despite his comedic appeal, which made him a familiar name in many homes, Allen experienced a turbulent upbringing.

In the year 1978, Allen was apprehended at a Michigan airport carrying more than a pound of cocaine. Facing a potential lifetime imprisonment, he chose to accept a plea bargain, spending over two years behind bars in a federal penitentiary. Released on parole in 1981, he managed to rebuild his life and ultimately rose to fame as a comedian and actor.

Christian Slater

Known for his roles in ‘Heathers’ (1988) and ‘Mr. Robot’ (2015-2019), Christian Slater excels at portraying unconventional characters. His powerful screen persona echoes a past that experienced turbulence in his personal life.

1997 saw Slater serving a three-month sentence due to an assault on his girlfriend, fueled by substance abuse and alcohol. Additionally, he spent 10 days in jail back in 1989 for driving under the influence. Despite these incidents, they didn’t halt his career progression, as he kept securing captivating roles.

Danny Trejo

Danny Trejo, famously known for his tough-as-nails characters in films like ‘Machete’ (2010) and ‘Sons of Anarchy’ (2008-2014), has an authentic background that significantly contributes to his iconic on-screen persona. Many of his raw, gritty roles are deeply rooted in his actual life experiences.

In his youth, Trejo was involved in selling drugs and had multiple arrests from as early as age ten. He served time in prison during the 1960s for robbery and drug-related crimes, with his longest sentence being served at San Quentin. However, he subsequently managed to reform himself, transitioning into acting and advocating for rehabilitation efforts.

Lillo Brancato Jr.

As a devoted movie enthusiast, I recall Lillo Brancato Jr., the talented man behind ‘A Bronx Tale’ (1993) and ‘The Sopranos’ (1999-2007), who shone brightly in his acting roles. However, his journey took a tragic turn due to personal battles with addiction, casting a shadow on his once-promising career.

In the year 2005, Brancato was implicated in a break-in that resulted in the fatal shooting of an off-duty police officer. Convicted for second-degree murder, he spent eight years behind bars until his release in 2013. Since then, he has been making efforts to restart his life and acting career.

Mike Tyson

Mike Tyson, who was once a heavyweight boxing champion and made an appearance in the 2009 film ‘The Hangover’, is recognized for his powerful persona that goes beyond the ring. His sports stardom later led to brief acting roles, however, his past has been marked by significant legal complications.

In 1992, Tyson was found guilty of sexually assaulting an 18-year-old girl in a hotel room located in Indianapolis. He was given a sentence of six years, but ended up serving only about three years in a federal correctional facility. Post his release, he ventured into acting and public appearances, consistently maintaining a contentious public image.

Tommy Lee

As a diehard fan here, I can’t help but admire Tommy Lee – the dynamic drummer from Mötley Crüe and the captivating actor in ‘The Dirt’ (2019). He’s got this larger-than-life persona that’s synonymous with rock stardom. His electrifying stage presence and personal life have been no stranger to tabloids, often making waves for reasons beyond the typical spotlight.

Back in 1998, Lee spent half a year behind bars due to an assault charge against his wife, Pamela Anderson, who was then his spouse. The conflict originated from a domestic altercation, further complicating his legal issues. However, he eventually went back to his career in music and acting, managing to preserve his rock image throughout.

Amy Locane

In the early ’90s, Amy Locane, famously recognized for her roles in ‘Cry-Baby’ (1990) and ‘Melrose Place’ (1992-1999), was on an upward trajectory as a promising young actress. However, a devastating incident significantly altered the course of her life.

In the year 2010, Locane received a conviction for vehicular manslaughter following a fatal car accident caused by drunk driving. The initial sentence was three years, but it was increased to eight years in 2020 due to a perceived leniency in the original ruling. She has completed her prison term and since then, she’s maintained a low public profile.

Michael Jace

Known for his performances in ‘The Shield’ (2002-2008) and ‘Forrest Gump’ (1994), Michael Jace excelled as a character actor, delivering captivating roles. However, his life took an unfortunate turn when he was involved in a shocking incident that left fans stunned.

Back in 2014, I found myself facing the unthinkable – the tragic and heartbreaking event of taking my wife’s life within our Los Angeles home. I confessed my actions to the authorities, who ultimately convicted me of second-degree murder. The court sentenced me to serve a term of 40 years in prison. This unfortunate incident marked the end of what had once been a thriving acting career, leaving behind a haunting legacy.

Robert Mitchum

In the realm of film noir, Robert Mitchum emerged as an iconic figure in ‘Cape Fear’ (1962) and ‘The Night of the Hunter’ (1955). Offscreen, he was more than just a Hollywood star; he carried a streak of rebellion. His casual demeanor belied a tumultuous past.

1949 saw Robert Mitchum spending a short spell behind bars due to a marijuana charge, further cementing his “rebellious” persona. This setback, however, did not hinder his progress, as he went on to be the leading actor in westerns and dramas, earning immense popularity among viewers.

Stephen Fry

Known for his work in ‘Blackadder’ from 1983 to 1989 and ‘V for Vendetta’ in 2005, Stephen Fry is a multi-talented performer and wordsmith. His sharp wit and captivating personality have been the hallmarks of his career, but his early years were marked by a misstep.

In his teenage years, Fry served a three-month sentence at Pucklechurch prison due to credit card fraud. However, he managed to transform his life for the better. He pursued education at Cambridge University and eventually gained recognition in the entertainment industry for his intellect and wit.

Bill Cosby

Known for his role as the TV father in ‘The Cosby Show’ (1984-1992), Bill Cosby, initially adored by many Americans, saw his comedic reputation crumble due to accusations which eventually resulted in a high-profile court case and conviction.

2018 saw Bill Cosby being handed a sentence of three to ten years in prison for the sexual assault he committed against a woman in 2004. However, after serving approximately three years, his conviction was reversed in 2021 due to an existing legal agreement. His case continues to spark heated debates.

Felicity Huffman

As a seasoned movie critic, I’ve always admired the versatile talents of Felicity Huffman, particularly her roles in ‘Desperate Housewives’ (2004-2012) and ‘Transamerica’ (2005). Her Emmy-winning performances have been a delight to watch. However, the recent news of her involvement in a scandal has left many fans, including myself, taken aback. It’s a side of this accomplished actress that I never expected to see.

In the year 2019, Huffman admitted guilt for her role in the college admissions scam by paying $15,000 to artificially inflate her daughter’s SAT scores. She served a portion of her 14-day sentence, which amounted to 11 days. Showing remorse and focusing on restoring her tarnished reputation, she moved forward post-release.

Lori Loughlin

Lori Loughlin, known for her role in ‘Full House’ (1987-1995), experienced a significant decline in public favor. The cherished character she portrayed as Aunt Becky was at odds with a substantial legal predicament.

In addition to being implicated in the 2019 college admission bribery case, Loughlin admitted guilt for conspiring to pay half a million dollars to guarantee her daughters’ university acceptance. After spending two months in jail, she has since resumed acting with a more subdued public profile.

Jamie Waylett

In simpler terms, Jamie Waylett, who portrayed the character Vincent Crabbe in the ‘Harry Potter’ films from 2001 to 2011, made an indelible mark as a bully on screen. However, his actions off-screen resulted in a significant slowdown or pause in his acting career.

In 2011, Waylett was found guilty of participating in violent disturbances during the London riots and was given a two-year imprisonment. Additionally, he had charges related to cultivating cannabis. The period spent in prison signified the termination of his acting career.

Lil’ Kim

The musician and actress known as Lil’ Kim, famously seen in ‘She’s All That’ (1999), carries an iconic image with a strong personality. Her legal issues were rooted in her unwavering loyalty towards her friends.

Back in 2005, I found myself facing a difficult chapter when I was sentenced to serve a year in prison due to a white lie about a 2001 shooting incident involving my crew that I had shared with a federal grand jury. After serving approximately ten months, I was granted freedom and couldn’t wait to get back to what truly matters – my music. The journey led me to earn some impressive Grammy nominations once more.

Danny Masterson

Danny Masterson, recognized for his role in ‘That ’70s Show’ (1998-2006), was a common sight on sitcom screens. However, his professional journey took an unexpected turn due to grave accusations that resulted in extended legal proceedings.

In the year 2023, Masterson was found guilty of sexually assaulting two women during the period from 2001 to 2003. He received a sentence of 30 years to life in prison, with the possibility of parole after serving 20 years. This case brought an end to his acting career as it attracted widespread criticism.

2025-07-29 08:16