In the world of glitz and fame, where red carpets and flashing cameras dominate, parallel experiences often escape the limelight—the stories of celebrities who went to jail and have found themselves on the wrong side of the law.
In this list, we put together 33 famous faces in random order who went through legal issues, from minor misdemeanors to more severe offenses. These accounts offer a compelling glimpse into the volatile relationship between fame and the criminal justice system, showcasing the diverse off-camera experiences that led these celebrities from red carpets to the less glamorous confines of jail cells.
#1
Robert Downey Jr.
In the 1990s, Robert Downey Jr. faced a battle with addiction and extensive legal troubles, resulting in incarceration. Arrested in 1996 for drug and weapon-related charges, he was given probation and mandatory drug testing. For probation violations, Downey served approximately 15 months in state prison in 1999 at Corcoran, California. Following his role in his last Marvel film, Robert Downey Jr. is now semi-retired from the entertainment industry.
#2
Wesley Snipes
In 2008, Wesley Snipes was convicted of filing false tax returns totaling millions of dollars, a crime for which he received a three-year sentence. He also incurred $5 million in penalties. After his appeal was turned down in 2010, Snipes was sentenced to federal prison, which he started serving in December of that same year. He was released in April 2013.
#3
Mark Wahlberg
Mark Wahlberg was convicted of racially motivated attacks in the 1980s. At the age of 15, he was charged with throwing rocks at black minors while yelling racial slurs. Later, in 1988, he physically attacked two Vietnamese men while high on PCP. Wahlberg was found guilty of violating the civil rights of his victims and was sentenced to two years in prison, serving 45 days. Despite controversies surrounding his past, Wahlberg has found success in his acting career.
#4
Khloe Kardashian
Khloe Kardashian’s brief stint in jail in 2008 places her among celebrities who went to jail for a March 2007 DUI incident. She was initially ordered to do community service and take alcohol education classes. She was sentenced to 30 days in jail for missing two weeks of her alcohol education course. Kardashian reported to a Lynwood jail in California on July 18, 2008. She served less than three hours of her 30-day sentence due to overcrowding.
#5
Lindsay Lohan
Lindsay Lohan was jailed and ordered rehabilitation multiple times during her legal troubles. Overcrowding in detention facilities and the nature of the offenses were frequently determining factors in how long she would spend in jail. Lohan was arrested for DUI, felony possession of cocaine, driving with a suspended license, and other charges related to probation violations.
#6
Chris Brown
Chris Brown faced a stack of legal issues; one of the major cases was the physical assault on then-girlfriend Rihanna, resulting in felony charges and significant legal consequences. His other offenses ranged from domestic violence to various altercations, drug-related incidents, and legal disputes. In May 2014, Chris Brown was sentenced to 131 days in jail for probation violations.
#7
Felicity Huffman
Felicity Huffman was imprisoned for 11 days in 2019 after pleading guilty to charges of conspiracy to commit mail fraud and honest services mail fraud in the college admissions scandal. She paid $15,000 to inflate her daughter’s SAT scores and received a 14-day jail sentence, a $30,000 fine, one year of probation, and 250 hours of community service.
#8
Amber Portwood
Amber Portwood’s incarceration in 2012 adds her name to the list of celebrities who went to jail after violating her probation related to a previous drug possession case. She was originally arrested in December 2011 for the possession of a controlled substance without a prescription. Portwood served 17 months in prison on drug charges until her release in December 2013.
#9
Lauryn Hill
Former Fugees member Lauryn Hill was charged with three counts of tax fraud in June 2012 for not filing taxes on $1.8 million of 2005–2007 income. She pleaded guilty and was released in October 2013.
#10
OJ Simpson
O.J. Simpson, a prominent name among celebrities, was found guilty of armed robbery in 2008 and was given a 33-year jail sentence in Nevada. The 1995 trial, in which he was notably cleared of all charges connected to the murders of his ex-wife Nicole Brown Simpson and her friend Ron Goldman, had nothing to do with this conviction. However, Simpson’s good behavior earned him parole in 2017, after he had served nine years.
#11
Danny Trejo
Danny Trejo was convicted of offenses involving drug sales and armed robberies and spent 11 years in and out of some of California’s infamous jails. After making a pledge to reform if given the chance in 1968, he became one of the most iconic celebrities who went to jail and changed his life for the better. He has been commemorating over 50 years of sobriety ever since.
#12
James Brown
James Brown was sentenced to six years in jail in 1988 for carrying a lethal weapon, fleeing police, and DUI. His shotgun waving and high-speed chase got him arrested. He was released in 1991 after serving half of his sentence. Brown faced further legal issues in 1998 and 2004, contributing to a complex legacy alongside his achievements in music.
#13
Lil Kim
Lil’ Kim spent over ten months in federal prison for lying about a shooting in 2001 before being released. Due to her good behavior, the rapper got out of prison early, despite being sentenced to a year and a day. After thirty days of house arrest, Lil Kim was under three years of supervised release.
#14
Chuck Berry
Chuck Berry, the legendary musician, faced legal challenges throughout his life, including prison terms for armed robbery at 17, violating the Mann Act in 1962, and tax evasion in 1979. Berry, despite legal troubles, left an indelible mark on rock and roll, portraying the multifaceted journey of celebrities who went to jail. His influence on rock and roll, with hits like “Maybellene” and “Johnny B. Goode,” was immense. Berry died in 2017, at the age of 90.
#15
Charles Dutton
Known for his parts in August Wilson’s pieces like “The Piano Lesson,” Charles S. Dutton had a turbulent history and spent nearly ten years in prison after being found guilty of homicide, possessing a deadly weapon, and fighting with a guard. While incarcerated, he developed a passion for theater, which changed his life.
#16
Lil Wayne
In 2009, Lil Wayne pleaded guilty to attempted criminal possession of a weapon after a loaded gun was found on his tour bus in 2007. He served eight months of a full year in prison in 2010. Lil Wayne pleaded guilty to illegally having a weapon and ammo on a private plane in 2020 and faces 10 years in prison. Before his January 2021 sentencing, President Donald Trump pardoned him.
#17
Merle Haggard
In 1957, 20-year-old Merle Haggard was imprisoned for attempted burglary. He tried to break into a Bakersfield restaurant but was arrested and imprisoned at San Quentin State Prison. California Governor Ronald Reagan unconditionally pardoned Haggard in 1972. He witnessed Johnny Cash perform for inmates and played in the prison band.
#18
Jared Fogle
Jared Fogle was arrested in July 2015. After pleading guilty to acquiring child pornography and traveling to engage in sex with a minor, he was sentenced to 15 years in prison in November 2015. Fogle will not be eligible for parole until March 24, 2029. He is currently completing his sentence.
#19
Mike Sorrentino
“The Situation” Mike Sorrentino was indicted for tax evasion on approximately $9 million in income and sentenced to eight months in jail in 2018. He admitted to one count of tax evasion and served time at the Federal Correctional Institution in Otisville, New York. Sorrentino, known for “Jersey Shore,” has since turned his life around. His turnaround post-prison illustrates the potential for rehabilitation among celebrities who went to jail.
#20
Sean Penn
Sean Penn spent a month in jail in 1987 due to confrontations with paparazzi. The confrontations led to legal trouble, but Penn’s career rebounded with successful movies, directing ventures, and accolades. In addition to his acting career, Penn is known for his political activism and humanitarian efforts.
#21
Ja Rule
Ja Rule, whose real name is Jeffrey Bruce Atkins, was sentenced to two years in state prison after entering a guilty plea in December 2010 to gun possession. In addition, Ja Rule received a term of 28 months in federal jail for tax evasion, which involved withholding taxes on earnings exceeding $3 million.
#22
Dustin Diamond
Dustin Diamond, famed for ‘Saved by the Bell,’ served three months of the four-month sentence in prison in 2015 for his role in a Wisconsin barroom stabbing. Diamond, who faced legal and financial challenges post-show, died at 44 after a three-week battle with carcinoma.
#23
Josh Duggar
According to prison records as of March 17, Josh Duggar’s federal prison sentence for possessing child sexual abuse materials has been extended to nearly two months, with his new release date set for October 2032. He was initially sentenced to 12.5 years in prison in May 2021.
#24
Monica Bedi
The meeting between Indian actress and presenter Monica Bedi and gangster Abu Salem during a stage show in Dubai altered her course in life. She received film opportunities as a result of their connection, but in 2002, Monica and Abu were detained in Portugal for using false documentation. She was then convicted of three years in prison by a CBI court, and she spent five years in prison (2002–2007).
#25
Tupac Shakur
Tupac faced legal troubles and imprisonment at various points in his life. In 1994, he served 15 days in jail for assaulting movie director Allen Hughes. In February 1995, he received a sentence of 1.5 to 4.5 years for the sexual abuse of a woman, stemming from an incident in 1993. In 1996, the 25-year-old rapper died in a drive-by shooting in Las Vegas, Nevada.
#26
Lillo Brancato
After being convicted of attempted burglary in December 2005, Lillo Brancato, Jr. served 8 years of his 10-year sentence. Off-duty police officer Daniel Enchautegui was slain during the burglary. He was found not guilty of Enchautegui’s murder. Brancato was freed from Hudson Correctional Facility in 2013.
#27
Harvey Weinstein
In March 2023, a Los Angeles court sentenced Harvey Weinstein to 16 more years. This sentence followed his February 2013 conviction for one count of rape and two counts of sexual assault. Weinstein is serving 23 years for rape and sexual assault in New York. The combined prison time for both convictions is significant after over 80 rape and misbehavior charges over decades.
#28
Lane Garrison
Lane Garrison was imprisoned for a fatal car crash on December 2, 2006. He crashed his car into a tree in Beverly Hills, California, while drunk and drugged, killing 17-year-old Vahagn Setian and injuring two others. Garrison received a 40-month sentence for vehicular manslaughter and DUI-causing harm in 2007. He served 27 months and was released in 2009.
#29
Suge Knight
The co-founder of Death Row Records, Suge Knight, was involved in a deadly hit-and-run in 2015, which led to a 28-year jail sentence in 2018. He also faced probation violations and assault charges. He served time in prison for probation violations from 1996 to 2001 and again in 2003. Knight’s release date is unknown, but his medical issues have caused delays in his court appearances.
#30
Julian Assange
Julian Assange is currently imprisoned at Belmarsh Prison in southeast London. His legal battles stem from the U.S. authorities’ pursuit of his extradition on 18 criminal counts related to the publication of classified documents by WikiLeaks in 2010 and 2011.
#31
Oscar Pistorius
Oscar Pistorius, the former Olympic runner, was denied parole and sentenced to another year and four months. He was convicted of murdering his girlfriend, Reeva Steenkamp, in 2013. The parole board found he had not served the “minimum detention period” for release. After several appeals, Pistorius was sentenced to 13 years and five months for murder in 2017.
#32
Ray Nagin
Ray Nagin was convicted of 20 charges of wire fraud, bribery, and tax evasion in 2014. Due to the COVID-19 pandemic, he was released to home confinement in April 2020 after serving over half of his 10-year sentence. Upon the Bureau of Prisons’ discretion, Nagin was released and is presently under federal probation in Dallas.
#33
Phil Spector
Phil Spector was sentenced to life in prison in May 2009 for murdering Lana Clarkson on February 3, 2003. Spector’s Alhambra house found 40-year-old Clarkson dead with a single gunshot wound to the mouth. A second-degree murder conviction in April 2009 added four years to Spector’s 19-year-to-life sentence after his first trial ended in a mistrial in September 2007. Spector died of COVID-19 on January 16, 2021, at 81, while serving his sentence.
These are the 33 celebrities who went to jail. They serve as a reminder that famous people, like everyone else, must deal with the intricacies of the human condition. Paying the price for their actions and occasionally emerging with a fresh perspective on life.