25 Celebrities You Didn’t Know Were Incarcerated

The US carceral state, responsible for housing one fifth of the global prison population despite Americans making up less than 5% of the world population, has ballooned enormously since the beginning of the war on drugs in the early 1970s. With nearly 75% of US states containing more prisons than colleges or universities, mass incarceration in the United States has even managed to circumvent the power and status of celebrity.

Mark Wahlberg

In April 1988 the former rapper, age 16 at the time, carried out a series of brutal racially motivated assaults on 2 Vietnamese men while high on PCP. Wahlberg would later be convicted of felony assault and sentenced to 2 years in prison, a term he would serve less than 2 months of. The Ted star would publicly apologize for his actions in 2006 and later seek a pardon for his convictions in 2014. Wahlberg would later rescind his request for clemency following public controversy in opposition to the motion.

Martha Stewart

The homemaking maven ignited a media frenzy in June 2003 following her indictment on 9 counts by the SEC relating to her role in the ImClone stock trading case. Stewart would later be convicted of 4 counts of obstruction of justice and lying to investigators, resulting in a 5 month stint in a West Virginia correctional facility. Despite this, Stewart was able to reclaim and rehabilitate her image of domestic perfection following her release in March 2005.

Khloé Kardashian

Good American founder Khloé Kardashian would be sentenced to jail in 2008 following probation violations stemming from her 2007 DUI arrest. Despite being sentenced to 30 days, Kardashian would be released just 3 hours into her incarceration due to prison overcrowding.

Zsa Zsa Gabor

In 1989, after being stopped for a traffic violation in Beverly Hills, the Hungarian-American socialite slapped the police officer who had pulled her over. After refusing community service in a plea deal, Gabor was sentenced to 3 days in prison, completing her stint from July 27th to July 30th 1990.

Wesley Snipes

After failing to report and pay income taxes from 1999 to 2004, the US government would charge and later convict Snipes of willful failure to file federal income tax returns. The ruling resulted in a 3-year prison sentence that Snipes would begin serving in December 2010 at a Pennsylvania correctional facility. Snipes would be released from prison in April 2013 and complete his period of house arrest in July 2013.

Tim Allen

In October 1978, more than a decade before rising to fame with his starring role in Home Improvement, Allen was arrested in an airport for possession of 650 grams of cocaine. Allen was able to avoid life imprisonment through a plea deal in which he provided the feds with the names of other dealers in exchange for a reduced sentence of 3-7 years. The Last Man Standing actor would be paroled in June 1981 after serving more than 2 years of his sentence.

Mike Tyson

Former boxer and current pigeon enthusiast Mike Tyson was arrested in July 1991 for raping an 18 year-old girl in an Indianapolis hotel room. The heavyweight champion would be convicted of the charge in February 1992 and subsequently sentenced to 6 years in a federal correctional facility, a sentence he would serve less than half of. As a result of his conviction, Tyson is required by federal law to register as a tier II sex offender for the remainder of his life.

Sean Penn

In 1987, while starring alongside Robert Duvall in the police procedural film Colors, Penn had an onset tantrum where he repeatedly punched an extra working on the film. Penn was convicted of assault in June of that same year and subsequently served 33 days of a 60 day jail sentence.

Mike "The Situation" Sorrentino

Following the massive success of Jersey Shore, Sorrentino became the second highest earning reality star in 2010 with reports of earnings exceeding $5 million, second only to Kim Kardashian. In September 2014 Sorrentino would find himself in a sticky, litigious “situation” after he’d been charged with tax fraud for failing to pay income tax on roughly $8.9 million in earnings.

Additional charges of tax evasion would be brought against the reality television star in April 2017, resulting in Sorrentino accepting a plea bargain in January 2018 for one count of tax evasion. The Situation would report to a New York correctional facility in January 2019 to complete an 8 month prison sentence, later being released in September of that year.

50 Cent

Following his ascent to de facto leadership of the East Coast rap group G-Unit, 50 Cent (born Curtis James Jackson III) rose to become one of the most influential men in the music industry. Prior to finding mainstream success, Jackson sold crack cocaine, a practice he’d begun at the age of 12. At 19, Jackson would be arrested for attempting to sell cocaine to an undercover police officer, carrying a possible sentence of 3-9 years in prison. Jackson was able to have his sentence reduced to a 6 month stint in a correctional boot camp in New York where he was able to obtain his GED.

Paris Hilton

In May 2007, the hotel heiress turned disc jockey was sentenced to 45 days in jail due to violating the conditions of her probation stemming from a slew of traffic violations. Hilton would report to a women’s prison in Lynwood, California on June 7, 2007 to complete her sentence. After just 19 days, Hilton would be released on June 26, 2007.

OJ Simpson

Despite his confounding ability to worm his way out of a conviction for the murder of his ex-wife Nicole Brown Simpson in what has oft been described as the most publicized trial of the century, Simpson wasn’t able to evade the penal system entirely. In 2008, Simpson would be convicted of robbery and kidnapping for his role in a 2007 robbery at the Palace Station hotel-casino in Las Vegas, charges that could potentially result in lifetime imprisonment. The former running back would be released from prison and granted parole in October 2017 for good behavior following nearly 9 years of incarceration. Simpson would later be released from the conditions of his parole in late 2021, ostensibly rendering him a fully free man.

Chris Brown

The disgraced singer has displayed a history of gross violent behavior since his assault of then-girlfriend Rihanna following an argument in 2009. Injuries sustained by Rihanna during the altercation would result in her hospitalization shortly after the incident. Later, in 2013, Brown would be arrested for felony assault in Washington D.C. following an altercation with a fan he refused to be photographed with. Brown would be jailed in a D.C. correctional facility for 36 hours before being released and ordered to report to his California probation officer within 48 hours.

Michelle Rodriguez

The Fast & Furious star has gotten herself into trouble numerous times through, perhaps ironically, getting behind the wheel of a car. In June 2004, the actress and screenwriter pleaded no contest to charges of hit and run, driving under the influence, and driving with a suspended license, landing her in jail for 48 hours. While filming Lost in Hawaii in 2005, Rodriguez would again be arrested on suspicion of DUI, a charge she would later plead guilty to and spend 5 days in jail as a result. Later, at an October 2007 hearing, Rodriguez would admit to violating the terms of her probation and be sentenced to 180 days in jail. Though anticipating serving the entirety of her sentence, Rodriquez would be released 18 days later due to prison overcrowding.

Christian Slater

In 1989, the Mr. Robot actor would be arrested for driving under the influence and consequently jailed for 10 days. Slater would be incarcerated again in 1997 following an assault on his then-girlfriend while under the influence of cocaine, heroin, and alcohol. After serving just 59 days of his 3 month sentence, Slater was released from jail for good behavior.

Ja Rule

The American rapper and co-founder of the disastrous grift Fyre Fest was first sentenced to 2 years in prison on December 3, 2010 following an arrest for possession of a firearm. Rule would later surrender himself into custody at New York City’s notorious detention center Riker’s Island on June 8, 2011. In July 2011, while serving time for his firearm charge, the rapper was given an additional 28 months in prison for failing to pay income taxes on roughly $3 million in earnings.

Rule would be released from state prison in February 2013 but immediately taken into federal custody to serve the remainder of his tax evasion sentence. The New York City rapper would finally be released from prison in May 2013 after serving roughly 2 years behind bars.

Danny Trejo

Machete actor Danny Trejo participated in his first drug deal at 7 and experienced his first drug arrest at just 10 years old. Trejo would spend much of the 1960s moving between California detention centers where he would eventually meet cult leader and convicted murderer Charles Manson who Trejo described as “greasy”. Trejo would be released from prison for the final time in 1969 and has been sober since.

Paul McCartney

On January 16, 1980 the Beatles frontman was arrested at a Tokyo airport for possession of nearly a half pound of marijuana after arriving in Japan to embark on an 11-city tour alongside his band Wings. The high quantity landed McCartney a smuggling charge, a conviction that could potentially carry a 7 year prison sentence. McCartney would be held in the Tokyo Narcotics Detention Center for 9 days before being deported back to England on January 25, 1980.

Felicity Huffman

The Desperate Housewives star was among the dozens of bourgeois parents federally charged for their connection to and role in the 2019 college admissions scandal (also known by its investigative codename Operation Varsity Blues). Huffman was accused of disguising a $15,000 payment to Key Worldwide Foundation as a charitable donation, while the “donation” was in fact a payment for another individual to take the SATs on behalf of Huffman’s daughter Sophia to achieve a higher score.

The actor would later be arrested at her California home on March 12, 2019 on charges of mail fraud and honest services fraud due to her involvement in the admissions scheme. On April 8, 2019 Huffman would plead guilty to one count of both mail fraud and honest services fraud and consequently be sentenced to 14 days in jail, a 1 year supervised release, a $30,000 fine, and to complete 250 hours of community service. The actor reported to a Dublin, California detention center on October 15, 2019 and would be released 10 days later on October 25, 2019.

Lori Loughlin

Like Huffman, Aunt Becky of Full House fame was implicated in the 2019 college admissions scandal after disguising a $500,000 bribe as a donation to Key Worldwide Foundation. In March 2019, Loughlin would be indicted on charges of fraud and bribery alongside her husband, designer Massimo Giannulli. Though initially denying the allegations, Loughlin would later plead guilty to charges of conspiracy to commit wire fraud and mail fraud on May 22, 2020 and would subsequently be sentenced to 2 months in prison. The sitcom actor would report to a federal corrections facility in Dublin, California on October 30, 2010 and was given a supervised release on December 28, 2020.

Teresa Giudice

The Real Housewives of New Jersey star, notorious for her explosive temper and exuberant spending, was handed a behemoth 39-count indictment on charges of conspiracy to commit mail fraud, wire fraud, bank fraud, and making false statements on loan applications on July 29, 2013. Alongside ex-husband Joe, Guidice agreed to a plea deal consisting of 41-counts of fraud and was consequently sentenced to 15 months in prison. In January 2015, the reality star surrendered to authorities at FCI Danbury to begin her 15 month stint and was released on December 23, 2015 after just 13 months.

Tommy Lee

The long-time drummer and founding member of the notorious heavy metal band Mötley Crüe spent 6 months in jail in 1998 after pleading no contest to assaulting then-wife Pamela Anderson whilst Anderson was holding the couple’s son, Dylan. Lee would return to jail for 5 days in mid 2000 for violating his parole by consuming alcohol.

Tom Sizemore

Embattled actor and convicted domestic abuser Tom Sizemore has had a plethora of run-ins with the law since gaining recognition for his role in 1989’s Born on the Fourth of July. In 2003, Sizemore would be convicted of domestic abuse against then-girlfriend and former Hollywood madam Heidi Fleiss after punching her in the face at a Beverly Hills hotel. After failing multiple drug tests in violation of his parole, Sizemore was sentenced to 7 months in prison in March 2005.

Dustin Diamond

The late Saved by the Bell actor was arrested in late 2014 after allegedly brandishing a switchblade during an altercation at a Wisconsin bar that ended with one man being stabbedr. On May 29, 2015 Diamond was convicted of carrying a concealed weapon and disorderly conduct resulting in a 4 month jail sentence he began in June of that same year. The actor would serve just 3 months of his sentence but would again be arrested in May 2016 after violating the terms of his parole. Diamond passed away from lung cancer on February 1, 2021 at the age of 44.

Amber Portwood

In 2010, the Teen Mom star would be charged with 3 counts of domestic violence following an investigation catalyzed by MTV airing disturbing footage of Portwood assaulting her then-boyfriend Gary Shirley. Additionally, a K-9 unit search was conducted at Portwood’s residency following her charges where authorities found her in possession of large quantities of both marijuana and crack cocaine.

After pleading guilty to 2 felony counts of domestic battery, Portwood would be given a 2-year suspended sentence alongside 2 years probation. Portwood would again be charged with domestic battery and briefly jailed in July 2019 after attacking former partner Andrew Glennon as he held their son James. Portwood reportedly threatened suicide and attempted to use a machete to break into a room where Glennon was hiding from Portwood alongside their son.

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