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While the lives of the rich and famous seem so idyllic, and for the most part they are, there are some celebrities who’ve led a less than picture-perfect life. In fact, some famous celebrities have gone to prison on charges ranging from tax fraud to sexual assault and even murder. Taking a look at celebrities whose legal woes have landed them in prison is a sobering reminder what glitters isn’t always gold — and the lives of the rich and famous are not always what they seem.
There’s a rather sizable amount of famous people who have done time in the big house. And some of them seem so squeaky-clean now, we still can’t believe they ever did anything wrong. Take, for example, Martha Stewart, who still is the reigning queen of domesticity all this time after she served five months in prison for lying to the feds. In the time since her stint in prison in 2004, Stewart has completely rebuilt her brand.
Then, there are stars who are trying to reclaim the fame they once had. Lori Loughlin was sentenced to two months in prison following her involvement in the 2019 college admissions scandal that found roughly 50 parents had bribed their children’s way into elite colleges. Loughlin ultimately pleaded guilty to one count of conspiracy to commit wire and mail fraud and was sentenced to two months in prison, then released a few days early. Now that she’s out, Loughlin has been trying to give her image some rehabilitation too — and get back into the acting game.
For more stories like these, and others that are even more serious, take a look at the infamous celebs who have been to prison.
A version of this article was previously published in March 2016.
In 2007, after a slew of traffic violations, Paris Hilton was sentenced to 45 days in a women’s prison.
Downey Jr. battled some major demons before becoming Iron Man. In 1999, he was sentenced to three years in prison after numerous incidents involving drug arrests and failure to comply with the courts.
In August 2000, he was released early after spending just about a year behind bars. He dabbled in cocaine after his release, but in 2005, put his turbulent past behind him to start a family and become the amazing actor we know him as now.
Former Theranos CEO Elizabeth Holmes started her 11-year prison sentence on May 30, 2023. Holmes was previously sentenced in November on three counts of committing wire fraud and one count of conspiracy to commit wire fraud.
Chrisley Knows Best stars Julie and Todd Chrisley reported to prison on Jan 17, 2023 for federal tax fraud convictions, Entertainment Tonight reported. Todd, who was sentenced to 12 years, reported to Federal Correctional Institution Pensacola in Florida, while Julie, who was sentenced to seven years, reported to the Federal Medical Center Lexington in Lexington, KY.
In March 2020, disgraced Hollywood producer Harvey Weinstein was sentenced to 23 years in prison after he was found guilty of criminal sexual act and rape in the third degree, per NPR.
In 2018, Bill Cosby was sentenced to 10 years in prison for drugging and sexually assaulting Andrea Constand at his home in 2004. A number of women came forward with similar stories to that of Constand’s account. In 2021, the conviction was overturned and Cosby was released from prison, per CNN.
After initially entering not guilty pleas to their charges, Lori Loughlin and husband Mossimo Giannulli eventually pleaded guilty to conspiracy to commit wire and mail fraud charges amid the Varsity Blues scandal. Loughlin was sentenced to two months in prison while her husband was sentenced to five months in prison.
Felicity Huffman spent two weeks in prison following the high-profile Varsity Blues scandal. Huffman pleaded guilty to fraud and conspiracy, after she paid $15,000 to have her daughter’s SAT test scores corrected, per PBS News Hour.
In 1987, actor Sean Penn was arrested for punching an extra on the set of his film Colors. At the time, Penn was on probation. He was sentenced to 60 days in jail and served 33 days, according to Us Weekly.
Spector, who was sentenced in 2009 for the second-degree murder of actress Lana Clarkson in 2003, was serving 19 years to life in a California prison. Spector died in January 2021.
Wahlberg was arrested in 1988 for assaulting a man named Johnny Trinh. Wahlberg was charged with assault and battery with a deadly weapon and possession of a controlled substance, and served 45 days of a 90-day sentence at Deer Island House of Correction. He petitioned to have the event stricken from his record, and Trinh has publicly said that he forgives Wahlberg for the incident. Wahlberg was 16 years old when he committed the crime, but now we know him for his various acting roles.
Snipes spent three years behind bars after being convicted in February 2008 of three misdemeanor counts of failing to file federal tax returns. He didn’t report to federal prison until December 2010, and he was released in April 2013.
“The biggest thing I got from it was learning the value of time and how we often squander it,” the actor told The Guardian of his time behind bars in 2020.
Since then, Snipes has kept himself busy acting, and appeared as Doc in The Expendables 3.
Before Allen became everybody’s favorite dad on Home Improvement, he was arrested in 1978 for trafficking cocaine. Though he faced life in prison, he served only five years for giving up the names of 21 people he had worked with in the drug trade.
Stewart served five months in prison for lying to feds about stock sales that went down in 2000. She was released in March 2005, according to CNN, and her domestic diva status has not floundered since her legal trouble. Stewart has, however, mentioned that she is having a bit of trouble in the love department.
T.I. was sentenced to 11 months in prison in October 2010 for breaking federal probation after he was arrested in LA on drug charges. He was released in September 2011, and then did a short stint at a halfway house. He previously served seven months in an Arkansas prison in 2009 after being arrested for trying to buy unregistered guns and silencers from undercover federal agents. In 2021, T.I. and his wife, Tiny Harris, were accused of sexual assault. In September of that same, the L.A. Times reported that the couple would not face criminal charges for a 2005 sexual assault case.
In 1992, Mike Tyson’s boxing career came to a halt when he was sentenced to six years behind bars after being convicted of the rape of an 18-year-old in Indiana. Tyson maintained that the incident was consensual, per The Sun.
Tyson was released in 1995 after severing almost half of his sentence.
In June 2012, Portwood was sentenced to five years in prison after violating probation stemming from felony drug-possession charges in 2011. She served a little over a year of the term and was released early in November 2013. Portwood seems to be doing well since her release, but suffered the loss of her father, who she says was instrumental in her recovery.
Brown was sentenced to 131 days in prison after being kicked out of court-appointed rehab for violating his probation for assaulting Rihanna by assaulting a man outside a hotel in Washington, D.C., in 2013. He was released in June 2014, after serving just three weeks of his term. More recently, Brown is back in the news. He’s being sued for allegedly drugging a raping a woman in Florida, per CBS News.
Hill served a three-month sentence for tax evasion and was released in October 2013. The musician quickly got back to work — she dropped a single on the eve of her exit from jail.
In 2010, Lil Wayne was sentenced to one year behind bars after an unlicensed gun was found on his tour bus in 2007. He served eight months before being released, and published a memoir about his hard time in January 2012.
When they were together, the Giudices faced some serious prison time. Teresa spent 11 months in prison for tax fraud. Though her sentence was 15 months, she was released early in December 2015, per ABC. The legal issues didn’t stop there, though.
Joe was sentenced to 41 months in prison, per Us Weekly, and began serving his sentence after his then-wife. But in October 2018, Giudice was ordered to return to Italy, essentially being deported. He has since been living in Italy.
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