Forget rehab, house arrest, community service and court dates. These celebrities have stood trial, pled guilty, or lost appeals. Going all the way is far much different for celebrities than normal citizens. The limelight, reputation and fame might be publicity, but sometimes it might be detrimental to your career.

Although so many celebrities have gone to jail for one reason or another, there are the A-listers who crossed paths with law enforcement while not very law abiding. The law has a way of catching up with criminals, and these criminals are famous for very different reasons. They are the top 10 most popular jailed celebrities in 2019.

10. Martha Stewart

Most Popular Jailed Celebrities 2019The 75-year-old businesswoman has been in the public limelight since the 1970s. She is known worldwide for her long-running television shows and also for her books. In 2001 Martha was convicted for insider trading. Stewart denied selling the ImClone stock just before the stock price plunged but further evidence proved that Martha had lied to the federal investigators. With this revelation the businesswoman was sentenced to five months in a federal prison. This, however, did not affect her public status. Martha Stewart was able to return to her company and she currently has a net worth of over $600 million.

9. Kiefer Sutherland

Most Jailed CelebritiesThe Canadian actor is famously known worldwide for the roles he has played in numerous hit series. He has played the role of Jack Bauer in the Fox hit series 24 and also as President Kirkman in the ABC political drama Designated Survivor. In December 2007 Kiefer was arrested for Driving Under Influence (DUI). Surprisingly, it was his fourth DUI charge in Los Angeles. After violating probation rules the 50-year-old actor cum director was sentenced to a 48-day jail term which he served without requesting an appeal. The jail spokesman said that Kiefer was very cooperative and that his conduct was above par.

8. Robert Downey Jr.

Most Jailed CelebritiesThe 51-year-old American actor is the man behind the Marvel Comics superhero Ironman. Robert began his career as a child and over the years became among the top actors in Hollywood. He has appeared on the Forbes rich list of the top paid celebrities for over five years running. He earned a reported $1 billion from the Avengers movie Franchise, Iron Man 3 and Captain America: Civil War. In 1996 Robert Downey Jr was arrested in California for being in possession of narcotics and a pistol in his car. He was sentenced to a one-year jail term but was pardoned on Christmas Day after he had successfully undergone rehabilitation.

7. Wesley Snipes

Most Jailed CelebritiesWesley Snipes were the star character in the Marvel Comics Blade where he played the role of Blade. The 54-year-old actor’s prowess in martial arts made him one of the most sought after actors in Hollywood in the late 1990s and the early 2000s. In 2011 the actor was sentenced to a 3-year sentence after the US Supreme Court refused to hear his appeal on tax fraud charges even though his lawyers argued that the sentence was too harsh for a misdemeanor federal mistake. Wesley Snipes was found guilty of failing to file his income tax in 1999, 2000 and 2001.

6. Mike Tyson

Most Jailed CelebritiesUndisputedly one of the all-time boxing greats Mike Tyson will be remembered for a very long time. His numerous public scandals surpassed the popularity of his boxing career. The 50-year-old is remembered for his infamous fight with Evander Holyfield in 1997 where he was disqualified during the eleventh round for biting his ear off. In 1991 Mike Tyson was convicted of raping a Miss America contestant. The Indiana court ruled that he would serve a sentence of no more than 6 years but the boxer was released in 1994 after just three years for good conduct.

5. Lil Kim

Most Jailed Celebrities

Lil Kim is among the pioneers of female rappers in the Hip-hop industry. Her career has been a huge success with her having released numerous albums that have been certified platinum. Subsequently she earned the title of “Queen of Hip-hop” in the early 2000s. in 2005 Lil Kim was prosecuted for lying in front of a grand jury when she tried to protect her friends who were involved in a shootout in 2001. She was served with a one year and a day jail sentence for trying to obstruct justice. She became the first big-female rapper to serve a jail sentence.

4. 50 Cent

Most Jailed CelebritiesCurtis Jackson was the big brains behind former popular Hip-hop group G-Unit. Curtis, famously know as 50 Cent, became one of the bestselling rappers in the world after he was discovered by Eminem and Dr. Dre who helped him launch his music career. The 41-year-old became famous after he survived nine gunshot wounds after a gun shootout in 2001. In 2005 the rapper was sentenced to six months in a concentrated boot camp for being in possession of an illegal fire arm that he had used on numerous occasions as a self-defense tool.

3. Lil Wayne

Most Jailed CelebritiesLil Wayne is an American rapper and one of the bestselling artists of all time. Dwayne Carter Jr, his real name, delved into music when he was a child but his partnership with fellow artist Birdman was the catalyst to his huge success. His music albums have earned him worldwide acknowledgement and even catapulted him to winning Grammys for the Best Male Hip-hop Artist on numerous occasions. In 2007 Lil Wayne was arrested for being in possession of a pot of marijuana and an illegal 40. Caliber semi-automatic gun. He served a one-year jail sentence.

2. Danny Trejo

Most Jailed CelebritiesWhen we talk of Hollywood all-time greats we cannot fail to mention Danny Trejo. He is most popularly known for his role as Machete in the Hollywood blockbuster movie Machete. He is also famous for his role in the movie Desperado. Before Trejo decided to pursue an acting career he was on the streets of California trying to make a name for him. He was involved in drugs and robberies with violence and was subsequently charged in a federal court with over ten counts of robbery. This landed him an 11-year jail sentence.

1. Ja Rule

Most Jailed Celebrities

The American rapper and actor made his big move to the Hip-hop music industry in 1999. In just six years he became one of the bestselling Hip-hop artists on the US Billboard Charts. His numerous feuds with G-Unit catapulted his career further up. In 2010 Ja Rule was sentenced to two years in jail. He was convicted of numerous counts of tax evasions and also for being in possession of a gun. He was released four months earlier because of good conduct. His release was highly anticipated by the Hip-hop world.

While the orange overcoat or jumper suit might be an unfamiliar fashion style for celebrities, sometimes not even the money counts. When the law comes beckoning, be sure a terrible mug shot will be the least of your worry. While most celebrities end up doing community service or been assigned parole officers, there are the above ten; their crimes required time away from the flashy lights and all things shiny.


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