Celebrities Who Had Short Stints In Jail
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This feature discusses drug and alcohol misuse and addiction.
Stars can find themselves on the wrong side of the law for a variety of reasons. In the past, well-known entertainers have served time for major felonies. In 2004, all-around businesswoman Martha Stewart spent five months behind bars for getting caught in a stock market lie, per The New York Times. On a heavier note, as of this writing, music mogul Suge Knight is serving a 28-year sentence for the death of a man in a hit-and-run incident, per CNN (Knight had pleaded no contest to manslaughter).
What does life in prison look like? You may ask. According to Stewart, it's not pretty. "Some of the food was dated, like, three years prior," the multiple-time author shared at a Daily Mail event. "If it was 2001, the food was expired in 1999 ... you would not want to eat that food. That's why I made jam out of the crab apples on the trees."
On the flip side, a number of popular figures have been apprehended and arrested for minor crimes which didn't result in jail time. They've included musicians like Green Day frontman Billie Joe Armstrong, who was apprehended for public indecency in 1995 after mooning his audience at a show, per MTV, and Kanye West, who was booked for vandalism after he was accused of smashing a paparazzi's camera, per TMZ. But there are some petty offenders who got a short-lived taste of the hard-knock life, instead. Keep scrolling to find out who they are.
Kim stole the show when Khloé went to jail
"Kim, would you stop taking pictures of yourself? Your sister is going to jail." These are Kris Jenner's viral words that put a stamp on the superiority of the Kardashian clan's never-ending one-liners. In 2007, Khloé Kardashian had gotten locked up for driving while intoxicated. However, she failed to honor taking part in an alcohol education course as part of her punishment, per E! News. As a result, the Good American co-founder received a 30-day sentence that birthed Jenner's quote while the family accompanied her to a Lynwood, California facility.
On Jenner's part, the moment was a reminder of the O.J. Simpson trial, during which her first husband, the late Robert Kardashian, was a defense attorney. "It was probably one of the hardest things that I'll ever go through in my whole life," she shared during a "Keeping Up With the Kardashians" confessional.
Khloé ended up serving only three hours of a 30-day sentence. According to TMZ, her short stint wasn't without its fair share of woes. An unnamed source told the publication that Khloé allegedly experienced solitary confinement, a prison lockdown, no clothing change, and cold conditions. "You don't wanna go there. It's not fun," she said on "KUWTK" afterward. "Being in there for 30 days, I would have died."
Will Smith hit rock bottom
Despite the fact that he was a Grammy-Award-winning artist, Will Smith was at his lowest in the early '90s when the IRS confiscated his belongings. On top of his financial problems, the then-rapper, who was yet to blow up on "The Fresh Prince of Bel Air," spent a weekend in jail for a crime he didn't commit.
In his memoir, "Will" (via Showbiz CheatSheet) the one-time Academy Award winner claimed that an altercation had ensued when his security guard, Charlie Mack, protected him from an alleged ambush during a radio station interview. The incident was said to have been orchestrated by Dana Goodman, a promoter who had worked with Smith and DJ Jazzy Jeff on their early work and who the duo purportedly replaced with Def Jam Records co-founder, Russell Simmons. When the attacker pressed charges, the star claimed that an old Pennsylvanian law known as the master-slave clause made Smith legally liable for Mack's actions and he spent a weekend in prison.
Not only was the star broke following his IRS troubles, but he had also recently split from his high school sweetheart. Lying on the cold floor of the prison, he came to the realization that his downward spiral had ultimately reached its threshold. "As I lay there in the fetal position, trying to figure out 'How the f*** did I get here?' I made the horrific error of clinging to the universal, rock-bottom axiom of hope, 'Well, I guess it can't get any worse than this.'"
Sherri Shepherd learned how to pay bills
When former "The View" host Sherri Shepherd was getting her career started in the '90s, she accumulated $10,000 in traffic violations, which led to her being thrown in jail, per Page Six. "The reason why it was $10,000, I feel very embarrassed, I was in this religion where they taught me that the world was gonna end, so I never paid my bills," Shepherd disclosed on "Sherri."
When she was finally released after eight days, the short-run during Martin Luther King Jr. weekend was enough for her to get back in focus, but it makes for a grim memory every time the holiday comes around. And while the star acknowledged that being in jail was by no means a good moment for her, she's still able to find some positives from the experience. "Jail, that was a classroom ... it was a life lesson, and now I pay my bills on time," Shepherd revealed in a conversation with Page Six. Shepherd also made a lifelong friend in jail, named Shelby who would often hype her cellmate up to others, suggesting she'd become hugely successful outside of prison. The pair kept in touch long after her release, and Shelby made it to the guest list during Shepherd's 2001 and 2011 weddings.
Michelle Rodriguez evaded long sentences more than once
As far as leaving jail early is concerned, "Fast X" star Michelle Rodriguez hit a lucky streak during the early days of her career. In 2004, she was handed three misdemeanor charges for a hit and run, driving under the influence, and driving with a suspended license, for which a 48-hour prison sentence was among her punishments, as reported by Entertainment Weekly. A year later, she was booked for another DUI, this time in Hawaii while filming "Lost." A police report from the incident accused Rodriguez of having behaved aggressively toward the authorities, per People. Although she was handed a 60-day sentence for breaking the terms of her probation, she ended up in custody for a breezy 24 hours instead, according to People.
Thankfully, the actor's barbaric days seem to be a thing of the past. Speaking to The Guardian in 2009, she suggested her newer look at life leaned toward maturity. "I'm [so] glad to be over my 20s, man," she said. "I used the excuse of adolescence to have enormous amounts of spontaneous fun. I've avoided responsibility for the last 10 years, now it's time to get on it."
Paris Hilton's time in jail was 'really scary'
In 2007, Paris Hilton received a 45-day jail sentence for violating probation, after she was caught driving after having had her license suspended just five weeks earlier, per Reuters (Hilton claimed she wasn't aware of the suspension). However, as reported by The Guardian, the "The Simple Life" star was let go from jail after three days and put under house arrest, instead. But no sooner had she basked in the joy of being free again, than the judge issued an order for her to serve her full term.
In footage published by AP News, Hilton's arrest caused commotion around her family home. She was noticeably devastated upon leaving the court and was seen in tears in the police car, all while the paparazzi were clamoring to capture the moment. The then-26-year-old was eventually released after 22 days for proper conduct, per Reuters.
During an interview with "Larry King Live," Hilton described what it was like to be detained. "Just the whole idea of being in jail is really scary. I hate to be alone, so that was really, you know, hard for me in the beginning," she said. The star added that she was haunted by constant nightmares of someone breaking into her cell to hurt her. Although she made a promise to reform, in 2010 Hilton plead guilty to drug possession and obstructing an officer after a small bag of cocaine had fallen out of her purse (she told the arresting officer that the purse wasn't hers), per Los Angeles Daily News.
Tems took her cellmates to church
In December 2020, singer-songwriter Tems was detained in East Africa. According to a tweet by the Ugandan Police Force, the "Essence" song sensation, alongside fellow Nigerian artist Omah Lay and her manager, Muyiwa Awomiyi, were indicted on a COVID-19 rule violation charge after doing a musical performance deemed to be unauthorized.
Awomiyi, alias Donawon, revealed through a conversation with the "Menisms" podcast that Tems took other detainees to church during her time in prison. "They had taken her [Tems] to the female section ... I was just worried about her," he shared. "I'll come to find out that Tems conducted praise and worship in the whole prison cell. Everybody was singing with her."
Additionally, Pulse.ng reported that Tems appeared to be on a hunger strike while in police custody. In a short clip showcasing an exchange between the 2023 Best Original Song Academy Award nominee and a female official, Tems appeared uncooperative, stating, "It's my body ... But what if I wanted to die? Then, you have no say. I don't want to eat." Two days after the arrest, Tems and her counterparts were set free, per BBC. In a since-deleted Instagram post, the musician expressed regret for the incident, stating, "I would never have participated [if] I had even the slightest knowledge that the event would not meet standard operating procedure and put Uganda citizens at risk."
Trevor Noah hid his arrest from his parents
Long before Trevor Noah was a host of "The Daily Show," the Grammy Award-winning comedian had a run-in with the law. In his book, "Born a Crime," Noah recounted the details of an arrest that occurred when he was in his teens. "Abel [Noah's ex-stepdad] also had a stack of old number plates in the back of the garage," he wrote. "I quickly learned I could just put one on an old car and hit the road."
In one instance, Noah's attempt at driving an unregistered vehicle caught up with him and the adolescent was stopped by the cops. He was tongue-tied upon interrogation and eventually wound up in a cell. However, it wasn't the police that sent chills down his spine, his parents did. "With my stepfather, I was thinking, 'He might actually kill me,'" Noah recalled. "In my mind that was an entirely realistic scenario. With my mother I was thinking, 'She's going to make this worse. She's not the character witness I want right now. She won't help me.'"
Noah made a phone call to a cousin who came to his aid and would later realize that the money to post bail had come from his mother. Needless to say, there was a tongue-lashing. However, the week-long jail experience was bittersweet — there was good food, books, and magazines to be read, but it came at the expense of seeing sunlight and simple things like having shoelaces.
Leslie Jordan shared a cell with Robert Downey Jr.
The late "Call Me Kat" star Leslie Jordan spent 27 days in LA Men's County Jail in 1997 after getting repeatedly booked for a series of DUIs. The beloved comedian had been in for 12 days when he felt his brain and body starting to hit their limit. In his description of the incident on "The Ellen DeGeneres Show," Jordan revealed that he tried to talk a guard into giving him a little break. "I'm having a panic attack ... can I take a walk?" he innocently asked, giving the officer an assurance that he would be back. His plea fell on deaf ears.
On the very last day of his sentence, Jordan had an encounter with "Iron Man" actor Robert Downey Jr. Thanks to overcrowding, the pair were cellmates for a number of hours. "They came to me and said, 'We don't have any room for him, he's downstairs waiting, but we can't let you out until 2 am,'" he shared in an interview with The Guardian. "It's a rule in California, that you can't let a drunk out until after the bars close."
In 2001, the two met each other again on the set of "Alley McBeal" and Downey Jr. couldn't quite recognize his one-time cellmate. Jordan explained, "He said, 'Didn't we? Are you?' and I said, 'Yep, 152, pod A, cell 13, you was top [bunk], I was bottom.'"
Nicole Richie served 82 minutes of a four-day sentence
In 2007, Nicole Richie was given a four-day sentence for reckless driving while under the influence of marijuana and pain medication. According to The Guardian, the "Great News" actor was speeding on the wrong side of a freeway when she was discovered by cops. She was released from prison after 82 minutes. During an appearance on "20/20" with her now-husband Joel Madden, a four-months-pregnant Nicole was certain that the offense would never repeat itself since she her daughter, Harlow, was on the way. "I never took it seriously before. As horrible as that sounds, I'm in a completely different place right now. I owe the baby my life and I have a responsibility now."
Her sentiments were echoed by her famous father, Lionel Richie, who was impressed that she handled herself with grace in spite of the attention she received from the press. Most importantly, she held herself accountable for her mistakes. "My father taught me to stand straight and take whatever punishment or hardships were the result of my actions and I am proud that I was able to hand that philosophy down to my daughter," Lionel said in 2007, per Us Weekly (via People).
Jane Fonda's mugshot was revolutionary
In 1970, Jane Fonda was starting a nationwide speaking tour about the Winter Soldier Investigation (WSI), sponsored by the Vietnam Veterans Against the War (VVAW). The hearing's aim was to highlight alleged war crimes and other atrocities purportedly committed by the United States Armed Forces and its allies in Vietnam, based on testimonies from the veterans who committed said acts.
According to an essay by the "Grace and Frankie" actor posted on her official website, after delivering her first speech in Canada, her luggage was seized upon re-entering the U.S. There, a box of vitamins was mistaken for illegal drugs and investigated alongside a book of contacts. "I told them what they were but they said they were getting orders from ... the Nixon White House," Fonda wrote. "I think they hoped this 'scandal' would cause the college speeches to be canceled and ruin my respectability."
She was arrested and placed in jail for 20 hours in Cleveland. The resulting mugshot, in which Fonda sported a low-high bang and raised her fist, sparked a movement. Subsequently, her nationwide college speeches recorded attendance in the thousands. There have been more activism-related arrests since, but Fonda hasn't waivered in her quest for awareness. During a 2020 appearance on "Jimmy Kimmel Live," she copped to receiving privileged treatment from the police, stating, "I'm white ... and famous ... you eat bologna sandwiches and then you get let out."
Matthew McConaughey thought it was 'a nice stay for a night'
In 1999, Matthew McConaughey was arrested for enjoying a very loud and super naked bongo session. Law enforcement officers made a surprise visit to McConaughey's high-end Texas residence following a local call. "I think I left a couple of windows open in the backyard. And I had a couple of new neighbors that I didn't get to know yet. And I think it woke them up," McConaughey disclosed about the early hours incident on "The Late Show with David Letterman."
The actor was detained at the Travis County Jail on the grounds of cannabis possession, ownership of drug-related equipment, and being resistant to arrest. He was formally indicted for the third felony. Speaking to David Letterman, he claimed the officers didn't knock on his door, but simply barged straight in. "I was buck-naked," he laughed.
McConaughey got out after a $1,000 personal recognizance bond was set. Jail apparently made for a decent temporary shelter. "I don't want to rent a place there, but it was a nice stay for a night,″ the "How to Lose a Guy in 10 Days" sensation remarked, having spent 10 hours in the slammer, per Associated Press. Although jail authorities hardly knew who they were dealing with at first, they soon found out when McConaughey's wallet gave away his star status.
Shia LaBeouf has been arrested five times
As of this writing, Shia LaBeouf has been to jail five times for small offenses. In the book "Prison Ramen," he opened up about multiple arrests, all of which led to short stints in jail. "The first time I was only nine years old. It was in Pacoima, California. I was arrested for stealing a pair of Nike Cortezes from a local shop and held for six hours," LaBeouf wrote in the book's essay, "Error Breeds Sense," per E! News. He was hauled in a second time for another petty theft two years later. LaBeouf was then locked up following an altercation with his neighbor that almost ended in a stabbing when he was twenty years old. LaBeouf's fourth arrest happened when he declined to exit from Walgreens, per Insider.
His fifth and final run-in with the cops was at a Broadway performance of "Cabaret," aged 28. According to Variety, the star had been disruptive during the show's first act including heckling the show's performers and smoking in the auditorium. He was escorted from the venue in handcuffs and spent approximately 25 hours behind bars. As LaBeouf recounted on "Jimmy Kimmel Live," it had been quite the night for him. In a drunken state, he had groped actor Alan Cumming during the performance, and spit on a policeman's shoe. He was subsequently charged with two counts of disorderly conduct and one count of criminal trespassing. In a 2021 episode of "Real Ones with Jon Bernthal," LaBeouf expressed regret for his past behavior and his desire to remain sober.
If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).
Paul McCartney was detained in Tokyo
Paul McCartney likes to go with the narrative that he was framed for marijuana possession in Tokyo back in the early '80s. But, in his own words, "I think I was just stupid. And I paid the penalty." According to the legendary musician's "Wingspan" documentary, it made no sense that he didn't conceal the drug when he traveled to the East Asian country, even after being forewarned that the punishment for being found with marijuana was seven years of hard labor.
"For some reason that I still can't explain, I took some in, and rather a large amount," McCartney chronicled. Memories of what led to his decision were still a blur, but the former Beatles band member clearly gave airport authorities an easy time in spotting the illegal drug. "I look back on that now and I can see the guy opening my suitcase, and right on the top, is this big gag of grass. I didn't even put it in a sweater or hide it."
McCartney spent nine days in custody and was ultimately deported. A planned concert was canceled, and his band, Wings, dissolved. As he divulged in the documentary, his experience in jail was brutal. Besides the consolation of a game he played with other detainees and a daily smoking break, he could barely get any sleep, experienced nightmares, wasn't given a change of clothing, and struggled with the language barrier.
Kim Richards was jailed for shoplifting
In August 2015, former "The Real Housewives of Beverly Hills" cast member Kim Richards found herself at war with the law when she was busted for shoplifting at Target. A source told Page Six that she'd attempted to leave with around $600 worth of merchandise — she ended up posting bail more than eight times the worth of stolen products. According to photos obtained by TMZ, the items in question included snacks, toys, beauty products, and stationery.
Earlier that year, Richards was taken into custody for causing disruption at the Beverly Hills Hotel. On "Watch What Happens Live With Andy Cohen," Richards, who has long been open about her experiences with alcohol addiction, explained what happened in the hours leading up to her arrest. At the hotel, a disagreement with an attendant over sitting space allegedly ensued. "He said, 'If you don't leave we're calling the police,' and I really thought he was joking, and he called the police. And one thing led to another," she expounded. She was held in jail for about nine hours where she was cited with public intoxication, trespassing, resisting arrest, and battery on a police officer.
In addition to a partial hotel ban, Richards was subsequently handed a three-year probation, a month of community service, and a year of Alcohol Anonymous meetings after being held for nine hours or so, per Daily Mail.
If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).