TV Shows & Movies
15 Great Shows That Started off Weak in the Beginning
15. 50 Cent
Before the platinum records, a 19-year-old Curtis Jackson was running drugs in Queens and got caught twice in three weeks in 1994, first for selling cocaine to an undercover officer, then in a home raid that turned up heroin, crack, and a handgun. Facing a sentence of three to nine years, he qualified as a first-time nonviolent offender and entered a "shock incarceration" boot camp instead. He came out about six months later with his GED, then pivoted toward the music career that made him a star.
| © FLAGRANT / YouTube
14. Lindsay Lohan
The Mean Girls star hit a turbulent stretch in the late 2000s, struggling with addiction and picking up two DUI arrests in 2007. Her jail time came later, in 2010, when a judge ruled she'd violated her probation by skipping court-ordered alcohol education classes. Sentenced to 90 days, she ended up serving only about two weeks thanks to jail overcrowding, one of several brief stints behind bars during those years. | © Netflix
13. Mike Tyson
At the height of his boxing fame, the heavyweight champion was convicted in 1992 of raping Desiree Washington, an 18-year-old contestant he met at a pageant in Indianapolis. A judge sentenced him to six years, and he served roughly three before his release in 1995. Tyson has always insisted he was innocent and falsely accused, though the conviction held up through appeals and still requires him to register as a sex offender. | © PowerfulJRE / YouTube
12. Phil Spector
The pioneering producer behind the Wall of Sound worked with everyone from The Beatles to The Ronettes before his legacy was overtaken by a killing. Actress Lana Clarkson was found fatally shot in his California mansion in 2003. Though Spector insisted she had taken her own life, a jury convicted him of second-degree murder in 2009 after an earlier trial ended in a hung jury. Sentenced to 19 years to life, he died in prison on January 16, 2021, at the age of 81. | © HBO
11. Mark Wahlberg
Long before Hollywood, a 16-year-old Wahlberg attacked two Vietnamese men in Boston on the same day in 1988, knocking one unconscious and striking the other while using racial slurs. Charged initially with attempted murder, he was convicted of assault and battery and sentenced to two years. However, he served only 45 days, alongside a contempt conviction tied to an earlier racist attack on Black children. He has said he "did the work" to change and apologized many times, but the past resurfaced in 2023 when critics blasted his choice as a SAG Awards presenter for the largely Asian cast of Everything Everywhere All at Once. | © Paramount Pictures
10. Robert Downey Jr.
Before he became Iron Man, the actor spent the late 1990s tangled in a brutal addiction that kept landing him in court. A 1996 arrest, when police found heroin, cocaine, and an unloaded handgun in his car, put him on probation, and repeated missed drug tests counted as violations. In 1999, a judge sentenced him to three years at a California state prison, where he served roughly a year before his 2000 release, long before the sobriety and comeback that followed. | © PowerfulJRE / YouTube
9. Martha Stewart
The lifestyle queen built an empire on home, cooking, and impeccable taste, which made her 2004 conviction all the more jarring. The case grew out of a well-timed 2001 ImClone stock sale, but the securities fraud charge was dropped, and she was found guilty of conspiracy, obstruction of justice, and lying to investigators, essentially the cover-up rather than the trade. Stewart served five months at a federal prison in West Virginia followed by five months of home confinement, then returned to TV and rebuilt her brand. | © Molly Sims / YouTube
8. Christian Slater
The Heathers actor hit a low point in 1997 after a drug- and alcohol-fueled bender ended with him punching his girlfriend and then shoving a police officer against a wall when they arrived. Convicted of assault, he was ordered to serve a three-month jail term followed by three months in a residential rehab facility. Slater ended up behind bars for 59 days before an early release for good behavior. | © The Kelly Clarkson Show / YouTube
7. Felicity Huffman
The Desperate Housewives star became one of the faces of 2019's Operation Varsity Blues, the sweeping college admissions scandal. She pleaded guilty to fraud conspiracy after paying $15,000 to have a proctor secretly correct her daughter's SAT answers. As the first parent sentenced in the case, Huffman got 14 days in jail, 250 hours of community service, and a $30,000 fine, and she walked free after serving 11. | © The Weinstein Company
6. Tory Lanez
The rapper, born Daystar Peterson, was convicted in December 2022 of shooting Megan Thee Stallion in the feet as the two left a Hollywood Hills party in July 2020. A jury found him guilty on all three felony counts: assault with a semiautomatic firearm, carrying a loaded and unregistered gun in a vehicle, and discharging a firearm with gross negligence. In August 2023, after the sentencing slipped more than once, a judge handed him 10 years in prison. | © hardknocktv / YouTube
5. Allison Mack
The Smallville actress, known for playing Clark Kent's close friend Chloe, pleaded guilty in 2019 to racketeering and racketeering conspiracy for her role in NXIVM. The group sold itself as a self-help organization but ran a secret subgroup in which women were coerced and exploited under founder Keith Raniere, who is now serving 120 years. Mack was sentenced to three years in 2021 and released early on July 3, 2023, after serving roughly 21 months. | © Walt Disney Pictures
4. Sean Penn
The actor racked up a string of violent run-ins through the 1980s, back when he was married to Madonna. The most serious came in 1987, when he punched an extra named Jeffrey Klein on the set of Colors while already on probation for an earlier assault. A judge gave him a 60-day jail sentence, bundled with a reckless driving charge, and he ended up serving 33 days behind bars. | © Warner Bros. Pictures
3. Danny Trejo
Long before Machete, the actor cycled through California's jails and prisons across the 1960s on drug and robbery charges. A 1961 stint in the Los Angeles County Jail put him near a then-unknown Charles Manson, a scrawny figure Trejo says he felt sorry for and agreed to look out for. Manson later claimed he could get them high through hypnosis, and Trejo swears the session worked so well he "felt the warmth flowing through my body," adding that Manson could have gone pro as a hypnotist if he hadn't turned to crime. | © Paramount Pictures
2. Brittney Griner
The WNBA star was detained at a Moscow airport in February 2022 after customs officials found vape cartridges containing hash oil in her luggage, legal in parts of the US but a serious offense in Russia. She pleaded guilty but said she'd packed them by accident while rushing, and that August, a court handed down a startlingly harsh nine-year sentence. Widely viewed as a political bargaining chip, Griner was freed that December after roughly 10 months in custody, released in a one-for-one prisoner swap for convicted arms dealer Viktor Bout. | © Reuters
1. Chris Brown
The R&B star pleaded guilty to felony assault after attacking his then-girlfriend Rihanna in 2009, drawing five years of probation, community labor, and domestic violence counseling rather than prison. His repeated probation troubles caught up with him later, including a 2013 assault arrest in Washington, D.C., that sent him to court-ordered rehab. After he was kicked out of that facility in 2014 for breaking the rules, a judge jailed him, and he served around three months before his release. | © Complex / YouTube
Fame and fortune don't put anyone above the law, and plenty of household names have learned that the hard way. From drug charges and assault to fraud and even murder, these stars all ended up behind bars at some point. Here are 15 celebrities who served time
