The glamorous world of Hollywood often seems worlds away from the harsh reality of life behind bars. Yet, when fame and jail time collide things often go astray. From household names to rising stars, some have experienced the cold, unforgiving jail cells. Being as it may, the unexpected twists and turns of the lives of celebrities who went to prison have always kept the public glued to the screen.
1. Danny Masterson
On September 7, 2023 a judge handed down a sentence of 30 years to life in prison to Danny Masterson, best known for his role on “That ’70s Show,” after he was found guilty of raping two women.
2. Lindsay Lohan
She has had several stints in jail, most of them having to do with probation violations and DUI charges.
3. Robert Downey Jr.
Downey struggled with drug addiction and was sentenced to jail two times, for a total of 19 months, both for skipping a drug test. Luckily for us, he successfully overcome his issues and made his big comeback as Tony Stark.
4. Martha Stewart
She served time because of some shady stock market stuff. It all started when she got a tip from her broker about a pharmaceutical company’s stock tanking. Instead of just sitting tight, she decided to sell her shares, avoiding a big financial, action for which she had to spend five months in jail.
5. Wesley Snipes
Wesley Snipes found himself behind bars due to some tax trouble. He somehow forgot to file his tax returns and the IRS takes that stuff seriously. He was convicted to 28 months in prison.
6. Mike Tyson
The boxing legend had a run-in with the law because of a nasty rape case back in the early ’90s. In 1992, he was convicted of raping Desiree Washington, an 18-year-old Miss Black America contestant, in an Indianapolis hotel room. The court sentenced him to six years in prison but he ended up serving about three years.
7. Paris Hilton
In 2007 she got pulled over for driving with a suspended license and got herself into more trouble when she was caught driving recklessly. These incidents were part of a larger issue because she had violated her probation from a previous DUI charge. The court didn’t take kindly to all of this, and as a result, Paris Hilton had to spend 23 days in jail.
8. O.J. Simpson
O.J. was famously acquitted of murder charges but later served time for robbery and kidnapping. He and a group of men stormed a hotel room in Las Vegas to recover what he claimed was stolen sports memorabilia. For that, O.J. Simpson was sentenced to 33 years in prison. He served about nine years before being granted parole in 2017.
9. Tim Allen
Tim Allen had a brush with the law back in the late ’70s. He got busted at an airport for possessing over 650 grams of cocaine, which is kinda huge. He managed to strike a deal, which gave him a reduced sentence of just over two years in prison.
10. Mark Wahlberg
Not many know this but he was involved in some serious trouble. One of them was an attack on two Vietnamese men in 1988, an attack for which he was charged with attempted murder. Wahlberg eventually pleaded guilty to some of these charges, and he was sentenced to two years in prison but only served 45 days due to the fact that he was still a minor.
11. T.I. (Clifford Harris)
In 2008, he got into hot water for trying to buy illegal firearms from a “cooperating witness.” T.I. took a plea deal and was sentenced to a year in prison. He served about eleven months behind bars.
12. Felicity Huffman
This was a hot topic at the time that made headlines in 2019 for her involvement in the college admissions bribery scandal, which exposed a scheme where wealthy parents paid to have their children’s SAT scores boosted or to secure spots on college athletic teams, even if the students didn’t play the sport. She was sentenced to 14 days of prison, being freed after 11 days, had to pay a $30,000 fine, to do 250 hours of community service, and a year of supervised release. Lori Loughlin was involved in this as well, for which she served a two-month sentence, was fined $150,000 and had to do 100 hours of community service.
13. Lauryn Hill
In 2013 she was sentenced to prison for tax evasion after she failed to pay federal income taxes on over $1.8 million in earnings over several years. She pleaded guilty and was sentenced to three months in prison.
14. DMX (Earl Simmons)
This guy had a tumultuous relationship with the law throughout his life. He faced a series of legal troubles, including drug possession, animal cruelty, reckless driving, and probation violations. All these culminated in 2018 with him being sentenced to one year in prison for tax evasion. He died three years later, in April 2021.
15. Lil Wayne (Dwayne Carter Jr.)
In 2007 he was arrested in New York City after a loaded gun was found on his tour bus. He pleaded guilty to attempted criminal possession of a weapon in the second degree and was sentenced to eight months in Rikers Island.
16. Bill Cosby
Famous for “The Cosby Show,” he was convicted in 2018 of aggravated indecent assault. He served about three years in prison before his conviction was overturned in 2021 due to legal issues. The case was significant in the #MeToo movement, with him being one of the few jailed celebs.
17. Diana Ross
Yes, Diana Ross is on this list too! She was arrested for DUI in 2002 for which she pleaded no contest to the charges and faced penalties, including 22½ hours of jail time.
18. Kiefer Sutherland
Kiefer Sutherland had quite a few DUIs under his belt. In 2007 he was arrested which led to a 48-day jail sentence. He faced another DUI arrest in 2009.
19. Ja Rule (Jeffrey Atkins)
The rapper had legal issues related to tax evasion and gun possession. In 2011 he pleaded guilty to failing to file tax returns for five years, resulting in a prison sentence. Additionally, he served time for illegal gun possession charges related to a 2007 concert incident. Grand total? About two years.
20. Nicole Richie
In 2006 she was arrested for DUI and later pleaded guilty. She was sentenced to four days in jail of which she served about 82 minutes and had to attend alcohol education classes as part of her sentence.
21. Michelle Rodriguez
The actress served 180 days in jail for probation violations related to DUI charges, along with lying having completed her community service.
22. Suge Knight (Marion Knight)
He was involved in various incidents, including assault and battery charges. However, one of the most significant legal cases was his involvement in a hit-and-run incident in 2015, where he was accused of running over two men, resulting in one fatality. In 2018 he pleaded no contest to voluntary manslaughter and was sentenced to 28 years in prison. He will not be eligible for parole until October 2034.
23. Gucci Mane (Radric Davis)
Radric Davis – by his legal name – faced legal issues related to gun possession charges. In 2014, he pleaded guilty to possession of a firearm by a convicted felon and was sentenced to 39 months in prison.
24. Tom Sizemore
The actor, who unfortunately passed away in march 2023, faced legal issues related to drug-related charges. In 2007, he was arrested for drug possession and subsequently sentenced to eight months jail time.
25. Jeremy Jackson
Best known for his role on “Baywatch,” he was arrested for his involvement in a stabbing during an argument. Jackson pleaded guilty to a felony charge and was sentenced to 270 days in jail, probation, and anger management classes.
26. Lil’ Kim (Kimberly Jones)
Lil’ Kim, whose real name is Kimberly Jones, had to deal with some perjury charges. In 2005 she was convicted of lying to a federal grand jury about her knowledge of a shooting incident for which she served a one year jail time.
27. Rick James
In 1993 he was arrested for assaulting a woman during a party at his home. He pleaded no contest and was sentenced to two years in prison along with being ordered to undergo counseling and drug rehabilitation.
28. R. Kelly (Robert Kelly)
Over the years, he faced multiple charges related to sexual misconduct, child pornography, and other crimes. In 2021, he was found guilty on multiple charges in a federal trial, including racketeering and sex trafficking. In 2023 he was sentenced to 20 years in prison.
29. Phil Spector
The legendary music producer was involved in a high-profile murder case. In 2003, he was arrested and charged with the murder of actress Lana Clarkson, who was found dead in his home. After a lengthy legal process and two trials, Spector was convicted of second-degree murder in 2009 and sentenced to 19 years to life in prison, ultimately dying in prison.
30. Josh Duggar
In May 2021 he was arrested and charged with two counts of receiving and possessing child pornography. These charges stemmed from his alleged possession of explicit images involving minors. He is currently in prison serving a 12.5 year sentence.
Recommended reading next: 17 Juiciest Celebrity Memoirs: The Good, The Bad And The Weird
Being a celebrity isn’t what it’s all that it’s cracked to be! From DUIs to tax evasion, and even more serious crimes, the stars we admire on screen or stage are, at the end of the day, human beings with their own ups and downs. These tales of redemption, resilience, and in some cases, continued controversy, remind us that the world of celebrities is not always what it seems. Regardless of the name of the celebrities who went to prison, one thing remains certain, fame doesn’t exempt anyone from facing the long arm of the law.
How do celebrity legal cases impact their careers?
Legal cases can have varied outcomes. Some celebrities see their careers stall or decline due to negative publicity, while others use their experiences to connect with their fans on a more personal level. Success in bouncing back depends on numerous factors, including the nature of the charges and public perception.
