19 Celebs Who I'm Positive You Had No Idea Went To Jail
- To start, it's been over two decades since Martha Stewart spent five months in prison for her insider trading scandal with stockbroker Peter Bacanovic. In 2004, she was found guilty of conspiracy, obstruction, and two counts of lying to federal investigators. She was released on March 4, 2005, and has been booked and busy ever since.
- Before his days as Iron Man, Robert Downey Jr. had some legal woes in the '90s. After being arrested for drug and weapon charges in 1996, he was required to undergo drug testing. He missed one, resulting in a four-month stint in the Los Angeles County jail. In 1999, he was sentenced to three years in prison after skipping another drug test. The actor served a total of 15 months before being released. Former California governor Jerry Brown pardoned him of his convictions in December 2015.
- In May 2007, Paris Hilton was sentenced to 45 days for violating probation in her alcohol-related driving case. She reported to jail on June 3 and was released by June 26.
- Khloé Kardashian was arrested for DUI in March 2007 and sentenced to probation for three years. After failing to complete roadside cleanup duty and enroll in an alcohol education class, the reality star was sentenced to 30 days in jail in July 2007. On July 18, she served less than three hours of her 30-day sentence and was released due to overcrowding.
- Lindsay Lohan took six trips to the Los Angeles County jail, but only spent less than two weeks behind bars for her convictions related to alcohol and drugs. Her shortest stay occurred on November 15, 2007, and lasted for only 84 minutes due to overcrowding in the facility.
- In November 2010, Lil Wayne was released after serving eight months at Rikers Island jail in New York for a gun possession charge. He was originally sentenced to one year, but got out early due to good behavior.
- Lori Loughlin pleaded guilty and spent two months in jail for her involvement in the 2019 college admissions scandal. Plus, she received a $150K fine, 100 hours of community service, and had a supervised release for two years. She was freed from jail in December 2020.
- Tim Allen was arrested in 1978 after being caught with over 650 grams of cocaine at the Kalamazoo/Battle Creek International Airport in Michigan. He could have faced life in prison without the possibility of parole, but ultimately only served two years and four months before being released in 1981.
- In 2008, Wesley Snipes was sentenced to three years in jail and fined $5 million for tax evasion. After his appeal was denied in 2010, he began his sentence at a federal prison that December and was released in April 2013. "I hope I came out a better person," he said. "I came out a clearer person."
- In 1987, Sean Penn was arrested for punching an extra on the set of Colors. He was already on probation and was sentenced to 60 days for the attack and reckless driving. The actor served 33 days in jail before his release.
- Lil' Kim was released in July 2006 after spending nearly 10 months behind bars in Philadelphia. In July 2005, she had been sentenced to a year and a day in prison and fined $50K for lying to a federal grand jury about a Manhattan shooting.
- Mark Wahlberg was a teenager when he served 45 days in jail for a 1988 attack on two Vietnamese men in Massachusetts. In 2014, he requested a pardon for the assaults, but dropped it two years later.
- Michelle Rodriguez had multiple jail visits in the '00s. In May 2006, she served four hours and 20 minutes of a two-month sentence for violating probation as a result of her DUI case in Hawaii. In January 2008, she was released due to overcrowding after serving 18 days of a 180-day sentence stemming from another probation violation.
- Felicity Huffman was another Hollywood celeb involved in the infamous 2019 college admissions scandal. She served 11 days of her two-week sentence, along with paying a $30K fine, serving 250 hours of community service, and one year of probation.
- In October 2018, Mike "The Situation" Sorrentino was sentenced to eight months for tax evasion. Additionally, he was ordered to complete 500 hours of community service, received $123,913 in restitution, and a $10K fine. He completed his jail time in September 2019 and became a free man once again.
- In 1999, Matthew McConaughey was arrested while dancing and playing the bongos naked in Austin, Texas. He was booked into the Travis County Jail for "possession of marijuana, possession of drug paraphernalia, and resisting transportation." The actor pleaded guilty to the misdemeanor charges and received a $50 fine for the incident.
- On January 16, 1980, Paul McCartney was found with nearly half a pound of marijuana in his luggage after arriving at Tokyo's Narita International Airport. This resulted in a nine-day stay at the Tokyo Narcotics Detention Center, and he was released on January 25, 1980.
- Before starting his acting career, Danny Trejo was in and out of custody for years for charges including armed robbery. During his time at San Quentin State Prison in California, he even became a champion boxer. Trejo later became a drug counselor and started working in Hollywood in the 1980s.
- Finally, Nicole Richie had a very short stay in jail for her DUI arrest in August 2007. She served 82 minutes of a four-day sentence and was released quickly due to overcrowding at the facility in Lynwood, California.
Posted May 10, 2026, 2:06 PM UTC
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