Nearly every role an actor takes is different from the previous one. That’s because no two movies are completely identical. Fans love watching creative stories unfold in front of their faces. There are some actors who don’t come from great backgrounds or who don’t make the best choices once they hit the big time, though. Whenever someone makes a mistake, they’re sent to prison as punishment – even if they’re famous.
One actor who’s famously spent time in prison is Wesley Snipes. During his time as an actor, Snipes became beloved by the masses for his role in countless action films. However, since he’s made so much money during his career, a spotlight was put on Snipes after the IRS found out that he wasn’t paying his taxes. After going to trial, Snipes was sent to prison for three years because of tax evasion.
Another actor who’s spent time behind bars is Bill Cosby. In the 1990s, people all over the United States saw Cosby as a father figure in “The Cosby Show.” He was adored by countless fans and his success continued to rise. However, there have been numerous women who have come out and claimed that Cosby assaulted them. After his trial, Cosby was sentenced to up to ten years in prison. His conviction was overturned, but he still did spend time behind bars. For more entertainment content, click here to read about 17 of the most iconic outfits in movies.
To compile this list of actors who are in prison or have served time, 24/7 Tempo consulted entertainment-related sources. These include SheKnows, IMDb, and The Marshall Project.
Robert Downey Jr.
LOS ANGELES, CALIFORNIA - FEBRUARY 24: Robert Downey Jr., winner of the Outstanding Performance by a Male Actor in a Supporting Role award and the Outstanding Performance by a Cast in a Motion Picture award for 'Oppenheimer' poses in the press room during the 30th Annual Screen Actors Guild Awards at Shrine Auditorium and Expo Hall on February 24, 2024 in Los Angeles, California. (Photo by Frazer Harrison/Getty Images)
After landing the role of Iron Man, Robert Downey Jr.’s life changed forever. He’s become one of the most successful actors in Hollywood history. He’s been in movies such as “Oppenheimer,” “Zodiac,” and “Sherlock Holmes” in addition to most of the MCU movies in some capacity. However, Downey Jr. didn’t always have a good head on his shoulders and sense of direction. Early on in his life, Downey Jr. was a drug addict.
He spent years trying to get sober and cleaned up. However, his addiction finally caught up to him and he was sentenced to three years of probation because of drug possession. Part of his probation stated that he would be jailed if he failed any drug tests. Downey Jr. failed a drug test during his probation, and was then sentenced to four months in jail. As of 2024, Downey Jr. is sober.
Wesley Snipes
Few actors in history have been in action movies that are as successful as Wesley Snipes. Growing up, Snipes practiced martial arts, something that would aid him big time in his adulthood. “The Water Dance” and “One Night Stand” are two of Snipes many performances that have left fans standing up and cheering once the movie completed. However, being a successful actor means you’re going to likely make a lot of money.
Making lots of money means you’re going to have to pay taxes on that income, whether you like it or not. For a while, Snipes avoided paying any taxes. That caught up to him once the government realized they were missing out on millions of dollars. After a lengthy investigation and trial, Snipes was sentenced to three years in prison for refusing to pay millions in taxes. He’s been released and is still making movies in 2024.
Mark Wahlberg
It’s normal for kids and teenagers to be reckless and make mistakes. Mark Wahlberg made mistakes that are hard to come back from during his time growing up in Boston. As a teenager, Wahlberg attacked multiple Asian-Americans in what seemed to be racially motivated assaults. Wahlberg showed little to no remorse for his actions at the time and was sentenced to three months in jail for his crimes.
After growing up and getting a new lease on life, Wahlberg has become an incredibly successful actor. He shows his versatility in every movie that he’s in. Fans saw a lighter side of Wahlberg in “The Other Guys” when he starred as a police officer alongside Will Ferrell. When Wahlberg was in “Pain and Gain,” the role was serious and he made few jokes. Wahlberg has also apologized for the attacks that he committed as a teenager.
Bill Cosby
Millennial growing up in the 1980s and 1990s thought of Bill Cosby as the dad they all wanted. In fact, because of his time on “The Cosby Show,” Bill Cosby was referred to as “America’s Dad.” He’s also been in countless other movies and TV shows that fans adore. Even early in his career, though, Cosby faced allegations around the assaults of numerous women. These were never taken seriously, as there was little evidence to advocate for the crimes.
In the late 2010s, there was one case that caught up to Cosby. He was tried and found guilty of assaulting a woman. For the crimes, he was sentenced to up to 10 years in prison. However, Cosby fought back and his conviction was overturned. Even though he was criminally free, Cosby still was forced to go to civil court to see if he needed to pay the victim for his crimes. He settled the civil lawsuit by paying one of his victims more than $3 million for his crimes.
Kiefer Sutherland
Few actors have the same career arc as Kiefer Sutherland. Most actors only star in movies or television shows. Few have made names for themselves in both forms of entertainment. Sutherland starred in the hit show “24” which follows Jack Bauer, a counter terrorist agent who is forced to make decisions that impact the world. Sutherland has also starred in movies like “A Few Good Men” and “The Canine Mutiny Court-Martial.”
In 2007, though, Sutherland was arrested for drunk-driving. After realizing his blood alcohol-content was far too high, Sutherland was sentenced to 48 days in jail. It was his fourth time being arrested for the crime. Sutherland has stayed on the straight and narrow path when it comes to alcohol since his most recent release. He’s continuing to make movies and television shows in 2024, and fans are still lining up to see him on screen.
Danny Trejo
Throughout his career, Danny Trejo has become an intimidating presence whenever he’s on screen. His handlebar mustache and big muscles make him the perfect person to star in action films and shows. Trejo has also shown a comedic and light-hearted side of himself in shows like “The Flash,” where he’s equally intimidating and willing to showcase his playful side. Trejo’s life wasn’t all rainbows and butterflies, though.
Growing up, Trejo participated in things he shouldn’t have been doing. The first time Trejo found himself behind bars was when he was only 12 years old. He was already an experienced drug dealer by this age and his first time behind bars seemingly didn’t change his outlook on life. Trejo spent so much time in jail that he even met Charles Manson during one of his stints. Finally, after years of uncertainty, Trejo turned his life around and has become a beacon of hope and good for those looking to do the same.
Tim Allen
It’s hard to imagine a world without Tim Allen entertaining people on screen. During his television career, Allen became known for his star role in the hit-show “Home Improvement.” The program helped Allen’s acting career get going. He’s found himself in multiple multi-movie brands, like the Toy Story and Santa Claus franchises. Allen’s sense of humor is why fans have adored him for decades whenever he’s been on screen.
Allen didn’t have a straight path to follow when becoming a star actor, though. In 1978, Allen was arrested at an airport for having more than 600 grams of cocaine that he was attempting to bring onto his flight. He pled guilty and helped law enforcement nab others involved in the operation. Because of his willingness to cooperate, Allen was only sentenced to a maximum of seven years in prison, rather than potentially serving the rest of his life behind bars. It’s safe to say Allen learned from his mistakes since he’s had no serious legal issues since.
Sean Penn
During his on-screen career, Sean Penn has become known for his stunts and amazing skills. In one of his biggest films, “Mystic River,” Penn played an ex-convict who ran a grocery store in Massachusetts. Penn won the award for Best Actor in the Academy Awards in 2004. Penn showed is versatility as an actor when he played Harvey Milk in the biopic, “Milk,” which told the story of the first openly-gay man to run for public office.
However, it hasn’t always been an easy road for Penn. During his career, Penn has had trouble keeping his emotions in check. While filming the movie “Colors,” Penn violated the terms of his probation when he punched someone on set. This, combined with a driving incident, landed Penn in jail for one month. During that time, Penn was placed near infamous serial killer Richard Ramirez who tried to befriend Penn. He held his ground and gave Ramirez no attention during their time together, though.
Danny Masterson
When “That ’70s Show” was on air, fans fell in love with Danny Masterson for his role as Steven Hyde. The fun-loving hippie character became a staple for Halloween costumes. Masterson, along with “That ’70s Show” co-star Ashton Kutcher, worked together again on a new project called “The Ranch.” Masterson played Jimmy “Rooster” Bennett for two seasons, until his past finally caught up with him.
In the early 2000s, multiple women accused Masterson of assaulting them. However, Masterson was aligned closely with the Church of Scientology. The church helped keep the victims mouths shut. After nearly 20 years of successfully doing that, the women finally came forward. Masterson was arrested, to the shock of numerous people. After a long trial, Masterson was found guilty of assault and sentenced to 30 years to life in prison. Masterson can’t apply for parole for 25.5 years, by which time he will be in his 70s.
Christian Slater
Action movies like “The Legend of Billie Jean” wouldn’t be the same without Christian Slater. He plays Binx, the younger brother of the main character, Billie Jean Davy. He also starred in the hit show “Mr. Robot,” where he played an anarchist who wants to add a cybersecurity specialist who’s proven he’s one of the world’s best hackers. During his career entertaining people, Slater’s won numerous awards including a Golden Globe for his role in “Mr. Robot.”
In the real world, Slater has had some trouble with following the law. He’s struggled with sobriety and his emotions throughout the majority of his career. The worst mistake came when assaulted his girlfriend and a police officer, while on a combination of multiple drugs. The event landed Slater in jail for two months.
Adam Hicks
There’s a stigma that most child actors don’t grow up to live normal lives. That’s exactly what happened to Adam Hicks. While growing up, Hicks became known for his roles in “How to Eat Fried Worms” and the Disney Channel show “Zeke and Luther.” It appeared that Hicks was on the right track for a successful career as an actor. However, his first run-in with law enforcement came in 2018. Hicks and his girlfriend were arrested under suspicion of armed robbery.
Before the trial, Hicks was deemed mentally incapable of being able to defend himself while facing his punishment. He wasn’t released from custody, but his trial was delayed until 2019. In 2021, Hick was sentenced to five years in prison for his role in the armed robberies. His girlfriend was only sentenced to three years of probation for what she did. Hicks was released in 2022, as the judge granted him with time served. Hicks has kept his name out of the media since his release from prison.
Jamie Waylett
Few movie franchises in the history of the world have been as successful as the Harry Potter franchise. Fans around the world loved watching the events that unfolded at Hogwarts. Jamie Waylett played Vincent Crabbe, one of Draco Malfoy’s best friends and loyal followers for the six movies in the franchise. However, Waylett didn’t see his acting career get much further than what it could have become.
Waylett was first arrested for the possession of marijuana in England, but that isn’t what landed the former “Harry Potter” star behind bars. During the August London Riots, Waylett was arrested for having the intention to steal products and incite larger riots. Waylett had a Molotov cocktail on him at the time of the riots, which is when someone has a flammable object that they intend on throwing to cause destruction. Waylett was sentenced to two years in prison for his role in the riots.
Charles S. Dutton
Growing up, Charles S. Dutton didn’t make sound decisions like most people. He was first arrested for manslaughter when he killed a man at the age of 18. He only served three years of this sentence, but was then arrested for violating the terms of his parole by owning a gun. He was sentenced to another jail term when he got into a fight with a security guard, which meant he got eight more years added onto his sentence.
Dutton has openly talked about his strange prison sentences saying, “I got three years for killing a black man and eight for punching a white man.” After his release, Dutton was determined to change his life and help people. He’s arguably most-known for his role in the show “Roc,” which follows Dutton as a garbage collector. He also starred in “The Piano Lesson,” a hit television film. Dutton has won numerous awards, including multiple Primetime Emmys and NAACP Image Awards.
Ryan Grantham
“Diary of a Wimpy Kid” was a novel and movie that tons of kids can relate to. Most kids want to fit in and grow up to be popular. Ryan Grantham played Rodney James in the hit movie. Another show Grantham had a key role in is “Riverdale,” the hit show on the CW. However, Grantham’s life and career didn’t go the way many people thought it was going to. Instead, Grantham did the unthinkable to most people in 2020.
Grantham shot and killed his own mother at their Canadian home in 2020, and even admitted that he considered murdering Canadian Prime Minister Justin Trudeau. Grantham decided against going after Trudeau, but was still in trouble for the murder of his mom. For his crimes, Grantham was sentenced to up to life in prison. He can apply for parole in 2036, which is 14 years after his sentencing took place.
Cameron Douglas
Coming from a family of actors and entertainers meant that Cameron Douglas was destined for the big-screen. His father, Michael Douglas, has become known for being in several successful movies. Cameron started his career in 1997 in the film “Mr. Nice Guy.” Douglas was starting to get his feet wet in acting when he was sent to prison.
Douglas was arrested for the intention to distribute drugs in 2007. He had large amounts of cocaine, heroin, and meth. For his crimes, Douglas was sentenced to five years in prison. His sentence ended with being sent to a halfway house in New York City. Douglas has turned his life around and has written a book discussing his life since then. For more entertainment coverage, click here to read about the 35 highest paid TV roles in history.