50 Celebrities Who Went To Jail For Minor and Severe Crimes

Trejo spent ten years, from 1959 to 1969, in and out of jail for various illegal substance-related charges. Before he entered the acting world, he launched a landscaping company after leaving the inner walls of the prison. He became a legend because of his performances in Spy Kids, Con Air, Heat, and From Dusk Until Dawn.

After a series of illegal substance possession and other charges, in 1999, Robert Downey Jr. missed a drug test and was sentenced to three years in jail. Luckily, he only served one year and was released. After these misfortunes, Downey Jr. changed his life and got some popular characters to play, including the career-changing Iron Man.

Paul McCartney wasn't famous enough to charm the Japanese authorities. McCartney was detained in 1980 at Tokyo's Narita International Airport for trying to enter the nation with half a pound of an illegal substance. To the authorities, nine days were enough to teach McCarney, and they set him free.

Martha Stewart, the famous television personality, was once arrested for a federal crime. In 2003, the US government indicted her on an outstanding nine charges of insider trading. She was a model prisoner and even earned a nickname — M Diddy. After prison, she began to rebuild her empire and even worked with Snoop Dogg for that much-needed marketing.

Oscar Pistorius, one of the most well-known athletes in the world and a double amputee, attracted the attention of his fans when he got detained for the homicide of his girlfriend, Reeva Steenkamp. Initially given a five-year sentence, the courts changed it to a longer 13 years and five months term.

Before becoming a rap legend with the release of his first album, 50 Cent was quite a troublemaker in his younger days. In 1994, 50 Cent got arrested for possessing illegal substances and a weapon. After serving six months in jail, he started his new life with a new nickname — 50 Cent.

After one night of naked bongos, the Texan Matthew McConaughey discovered himself in a prison cell. In 1999, police got called to his residence, where they found a naked McConaughey, high on illegal substances. His one night spent in jail only built his legendary icon status and helped give meaning to his saying — alright, alright, alright.

At age 16, he assaulted two Vietnamese Americans while yelling racial epithets. For this, Wahlberg was given a two-year sentence but only served 45 days. Four years later, Wahlberg shattered his neighbor's jaw in an assault, and the case got settled out of court. He changed his ways over time and became quite a star.

A$AP Rocky was imprisoned for a month in a Swedish jail in the summer of 2019 as authorities looked into his involvement in a fight with a guy on the streets in Stockholm. Despite the claims that he was protecting himself, Rocky was found guilty of assault. Luckily for him, he didn't get any additional jail time.

Michelle Rodriguez initially got a 60-day jail term for breaking her probation in 2006, but she only stayed behind bars for four hours and 20 minutes. The actress broke her probation once more a year later. She later admitted to abusing alcohol while donning a monitoring bracelet at least three times and failed to finish her community service.

Tim Allen was taken into custody on October 2, 1978, with 1.43 ounces of illegal substances on him. Allen gave up his dealers to avoid a life sentence, and following a brief stint in jail, Allen turned to comedy and didn't look back. His flourishing career shows that he made the right decision.

Member of the Hilton family, Paris Hilton used to be a headache for law enforcement. It all began in 2006 with a DUI arrest. Then, Paris Hilton ignored the license suspension and served a 45-day term in the Lynwood Detention Center before being let out if she promised to behave correctly.

Lil Wayne, also known as Dwayne Michael Carter Jr., was initially detained in July 2007 for possessing a firearm. Wayne first entered a not-guilty plea but changed his stance to guilty in return for a shorter sentence. The rapper was in prison on New York City's Rikers Island for eight months.

Charlie Sheen was detained on Christmas Day in 2009 following a fight with his ex-wife Brooke Mueller. He was jailed for the remainder of the holiday on charges of second-degree assault, threatening, and criminal mischief after being arrested in an Aspen prison. Charlie eventually entered a plea of guilty to a misdemeanor third-degree assault charge.

It’s hard to talk about celebrities and jail without mentioning Sean Penn. While he didn’t do anything huge, he was known for being extremely hostile towards co-stars and paparazzi photographers. On the set of his movie Colors, Sean Penn hit an extra. He was on probation at the time. He received a 60-day sentence, of which he served only 33 days.

A person that is hard to forget, Abby Lee Miller was given a 366-day prison term for trying to hide $775,000 in television revenue in the Chapter 11 bankruptcy case. To avoid a long sentence in prison, she pleaded guilty. In prison, she took the time to prove her health, lose 100 pounds, and found the time for studies too.

After the success of the American Pie movies, Chris Klein struggled not only with finding the next big part but also with the courts. In 2010, Chris Klein was arrested and jailed for four days for drunk driving. He was previously guilty of the same thing in 2005. After these two incidents, it seems like he has fixed his life for the best.

Boy George, a member of Culture Club, was imprisoned for four months when the Norwegian male escort Audun Carlsen was attacked and imprisoned in the singer's London apartment in 2007. He was found guilty of using excessive force and had to spend 90 days under house arrest.

Mike Tyson might have the ultimate redemption arc. After being sent to jail for multiple reasons, Tyson served only three years of his six-year sentence. After appearing in a few boxing matches and going bankrupt, he started a podcast, opened a business, and lives happily now, making more money than he did while boxing.

The former child actor frequently got detained for driving while intoxicated and having a variety of illegal substances in her possession. Although Lohan battled addiction and repeatedly checked herself into rehab over the years, she tried hard to restart her career, even signing up to work with Netflix.