Celebrities Who've Done Time — and Still Built Successful Careers

The life of a celebrity is not always glamorous. From scandals and irresponsible spending causing them to lose everything, the pressures of being famous don’t often come without consequence. Just ask Mike Tyson, who has tried to turn his life around after a rape conviction with business ventures and charity work, but who again finds himself in the news for punching an airline passenger. Still, falling from grace doesn’t have to be permanent. Some celebrities have done time behind bars and were able to turn their lives around, make a comeback, and build seriously successful careers.

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In 1991, Mike Tyson was arrested for the rape of an 18-year-old and was sentenced to six years in prison plus four years of probation. Tyson was released after serving less than three years of his sentence. After his release, the boxer won multiple comeback bouts with ease, with his first fight grossing nearly $100 million worldwide. He has also built a successful multi-million dollar cannabis business, with one of the products being an ear-shaped edible. Tyson is currently in the news for allegedly punching a fellow plane passenger in the head after the passenger was reportedly harassing him. 

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In 1996, Robert Downey Jr. was arrested for possession of cocaine, heroin, and an unloaded .357 Magnum as he was speeding down Sunset Boulevard. A month later, he trespassed into a neighbor’s home while under the influence and fell asleep in one of the bedrooms.  As a result, he received a three-year probation sentence that required him to participate in mandatory, random drug tests. After missing a drug test in 1997, he was sentenced to six months in jail. In 1999, he missed another and was sentenced to three years in prison, of which he served nearly a year before being released. Downey Jr. didn’t let his time behind bars derail his acting work after his release. He went on to star in several blockbuster films and even landed the role of Iron Man in multiple “Iron Man” and “Avengers” movies.

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At just ten years old, Danny Trejo was arrested for the first time. Two years later, he experienced his first incarceration at Eastlake Juvenile Hall. Trejo spent eleven years going in and out of the prison system for robbery and drug dealing. His final prison sentence began in 1965 when he was caught selling four ounces of heroin to an undercover federal agent. During that sentence in 1968 (Trejo was 24), he was involved in a prison riot that earned him solitary confinement after he hit a guard in the head with a rock. He was released after serving five years of his ten-year sentence. After his release, Trejo got sober and began working as a substance abuse counselor. In 1984, he was called on-set to help an actor who was struggling with his own sobriety — and got cast in the film. He has since appeared in at least 150 different movies and TV shows (though some estimates are much higher). He's also now the owner of a rapidly growing restaurant empire based out of Los Angeles, which includes Trejo's Tacos, Trejo's Cantina, Trejo's Coffee and Donuts, and recently co-authored a cookbook.

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Before becoming a household name thanks to his starring role in the hit sitcom “Home Improvement,” Tim Allen served nearly two-and-a-half years in prison. Allen was arrested in 1978 at the Kalamazoo/Battle Creek International Airport in Michigan for possession of more than 650 grams of cocaine. He pleaded guilty to felony drug trafficking charges and to evade potential life imprisonment, he provided the names of other drug dealers. 

After being found guilty in 2008 of willful failure to file federal income tax returns, Wesley Snipes reported to serve his sentence in 2010. Snipes filed for an appeal in 2011 which the Supreme Court declined to hear. He was released in April 2013 and remained on house arrest until that July to finish out his sentence.  Snipes’ acting career didn’t end with his prison time. He continues to star in feature films to this day including 2019’s “Dolemite Is My Name” and 2021’s “Coming 2 America.”

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Despite several hit records and a high-profile career, Chuck Berry came under fire in 1959 when he was arrested for allegedly engaging in sexual intercourse with a 14-year-old waitress. Berry was convicted after a two-week trial and sentenced to five years in prison. He appealed the ruling citing that the judge exhibited racist behavior toward him, influencing the jury against him. His appeal resulted in a second trial that again found him convicted, this time with a three-year sentence. Berry tried and failed for another appeal and ended up serving one-and-a-half years in prison. Not only did Berry continue performing and recording new music during his trials, he hit the ground running after his release with dozens of chart-topping albums and singles and a career that continued for nearly 60 more years.

Following a highly publicized trial in 2004 sparked by securities fraud and obstruction of justice, Martha Stewart was found guilty of felony charges of making false statements to federal investigators, conspiracy to obstruct, and obstruction of an agency proceeding. Stewart served five months in prison and two years of supervised release. Stewart’s jail time brought her even more notoriety and she launched a comeback campaign after she served her time, notably teaming up with Snoop Dogg for projects like 2019’s “Martha & Snoop’s Potluck Party Challenge,” bringing her more success and profitability than before her arrest. 

Before his rise to fame, Merle Haggard spent some time in and out of prison. He was arrested in 1957 for attempted robbery and was held at the Bakersfield Jail after being convicted. Upon trying and failing to escape, he was transferred to San Quentin Prison where he was fired from several prison jobs and did time in solitary confinement. During his imprisonment, Haggard was inspired by a Johnny Cash performance at the prison. He was released in 1960 and became a country music star over the next decade.

As a teenager, Mark Wahlberg was involved in multiple racially-charged, violent incidents. At 16, Wahlberg assaulted a Vietnamese-American man on the street, using a large wooden stick to knock him unconscious. Wahlberg was arrested and charged with attempted murder. He pleaded guilty to felony assault but only served 45 days of his initial two-year sentence. Despite a rocky road in his younger days, Wahlberg has found success as an actor in both comedies and action films, not to mention his business endeavors, which include a burger chain that he owns with his brothers called Wahlburgers, a Chevrolet dealership, and the online platform Ballers Report.

Tommy Lee and Pamela Anderson had a tumultuous relationship that was highly publicized. In 1998, Lee served six months in county jail after being arrested for kicking Anderson while she held their son. Lee went on to have a prolific music career both as a solo artist and with Mötley Crüe.

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