The Biggest Celebrity Prison Sentences That Were Cut Short

The following article includes discussion of sexual assault, alcohol and other substance abuse, and child abuse.

Over the past few years, culture has taken a long, hard look at the criminal justice system, calling for reform from every corner of society. Documentaries like "Making a Murderer" became massive hits by examining potential cases of wrongful incarceration. Kim Kardashian has pursued a career in law to help free people who should not be in prison. Rapper Drakeo the Ruler released an urgently political album in 2020 to great critical acclaim, having recorded it entirely over a prison phone system, because he was still sitting in lockup despite being acquitted of the charges he was originally sent away for. And, of course, the Black Lives Matter movement reached new heights in 2020 after the murder of George Floyd, becoming perhaps the largest sustained social justice protest in American history, per The New York Times.

All of these aspects of culture make one thing clear: the justice system isn't always applied equally. That's especially evident in the case of celebs who have gone to jail, many of whom found themselves on the receiving end of some leniency not always afforded to those who don't have the same level of fame. Thanks to numerous factors, including successful appeals, overcrowding in the jail systems of Los Angeles, good behavior, medical issues, and even the intervention of higher courts, many stars have had their prison sentences cut short. Read on for a roundup of some of the biggest offenders and the details surrounding their early releases.

In the early years of the Kardashians' budding media empire, Khloé Kardashian was arrested for driving under the influence in 2007. She appeared on Tyra Banks' talk show (via People) and told the host that she was glad no one was hurt or killed. "What I could have done is just unthinkable. I will never, ever do that again," she swore.

However, she missed her court-mandated alcohol education classes, and she skipped out on her road-cleanup community service responsibilities, meaning she had to report to prison as a result. In the car on the way there, Season 1 "Keeping Up With the Kardashians" cameras rolling dutifully, older sister Kim wouldn't stop snapping selfies. This led to frustrated momager Kris Jenner uttering the now-iconic line, "Kim, would you stop taking pictures of yourself? Your sister is going to jail!"

"Khloé is ready and willing to serve out her sentence, no matter how long and where, and have this resolved," her representatives told People. However, even though she was sentenced to 30 days in prison for the probation violation, People reported that Khloé ultimately served a whopping three hours due to overcrowding.

It seems the famous family hasn't let their little sister forget about her time as a jailbird. Kim posted the selfies from the car years later, and according to US Weekly, it seems that both Kim and her mother have Khloé's mugshot displayed prominently in their homes!

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).

Controversial rapper Tekashi 6ix9ine has been dogged by legal trouble his entire career. The rainbow-haired artist behind hits like "GUMMO" and "FEFE" was born Daniel Hernandez, and he pled guilty in 2015 to charges of using a child in a sexual performance. As Pitchfork reported, Hernandez was sentenced in 2018 to four years of probation rather than jail time.

Later that same year, TMZ broke the news that Hernandez had been arrested on racketeering and firearms charges related to his alleged involvement in the gang known as the Nine Trey Bloods. He fully cooperated with the investigation, giving up the names of other members of the gang, in order to avoid a possible life sentence. "I know God has a bigger plan for me. I want to inspire the youth that it's never too late to change," he said in a statement at his sentencing, via the Inner City Press.

The jail time he'd already served counted toward his two-year sentence, but Hernandez was released several months early anyway. "COVID-19 presents a heightened risk for incarcerated defendants like Mr. Hernandez with respiratory ailments such as asthma," wrote Judge Paul Engelmayer in the order granting Hernandez his freedom (via ABC News). On Instagram Live shortly after his release, Hernandez said, "You know why people so mad? Cause they thought it was over for me. They counted me out. ... Y'all could never cooperate with the government and come back. ... I'm a living legend."

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Before he was the star of '90s mega-hits including "Home Improvement" and "Toy Story," Tim Allen was just a normal stand-up comic — one who found himself arrested for being in possession of more than a pound of cocaine in 1978. Per CBS, Allen took a plea deal and cooperated with the investigators, voluntarily giving up the names of other drug dealers in order to get his sentence reduced. "I pleaded guilty," Allen told the Los Angeles Times. "I knew what I did was wrong, I did not drag it out in a trial. ... I laid down. Punish me." Though he was ultimately sentenced to 3-7 years in prison, he was granted parole a little over two years later.

On an episode of WTF with Marc Maron, Allen reflected on his time in the big house. "I learned literally how to live day by day. And I learned how to shut up. You definitely want to learn how to shut up," he said. Speaking to Closer Weekly, he elaborated on what his run-in with the law meant for his ability to turn his life around and ultimately become a major Hollywood star. "It was a watershed moment," he admitted. "It put me in a position of great humility, and I was able to make amends to friends and family and refocus my life on setting and achieving goals."

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).

Troubled former child star Lindsay Lohan has repeatedly lucked out when it comes to having her jail sentences reduced. Her initial stint in the clink — the result of drunk-driving charges and possession of cocaine — was supposed to be one day long, but she only served 84 minutes of the sentence due to overcrowding. "It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs," she confessed in advance of serving her time, according to the Associated Press (via Today). 

In 2010, Lindsay was sentenced to 90 days in jail for probation violations after she admittedly did not attend alcohol counseling sessions she had been ordered to complete by the court, per CNN. Lohan sobbed as the sentence was read aloud. The Guardian reported that she was in solitary confinement while in prison, and she ultimately was released early for good behavior and due to overcrowding. She had only served 14 days of the three-month sentence.

She was later sentenced to 120 days in jail for the much-publicized theft of a necklace, but according to Reuters, she was permitted to serve just 35 days under house arrest instead. The Hollywood Reporter noted that she used her time at home to film a commercial, advertising Beezid.com with a coy reference to the state of her confinement. "Hey to all my friends. I just want to share with you that during some of my time at home, I found this amazing site with great deals," she said.

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).

In 2014, comedian Hannibal Buress ignited a firestorm when he called out Bill Cosby onstage for the allegations of rape that had piled up over the years. "That s**t is upsetting. If you didn't know about it, trust me. You leave here and Google 'Bill Cosby rape,'" Buress told his audience (via Vulture). "It's not funny. That s**t has more results than Hannibal Buress." Buress' efforts to bring awareness to the situation got the ball rolling, and in 2015, 35 women who say Cosby sexually assaulted them appeared on the cover of New York Magazine.

In 2018, Bill Cosby was sentenced to 3-10 years in prison after being convicted of sexual assault, per CNN. A year later, he told a reporter for Black Press USA that he expected to serve his full sentence because he would not be apologizing. "I have eight years and nine months left. When I come up for parole, they're not going to hear me say that I have remorse," he said.

However, his conviction was overturned in 2021, and he was released early. A prosecutor had told Cosby he wouldn't be charged, and the Pennsylvania Supreme Court decided it was unfair that Cosby was later charged anyway, per AP News. After getting out, Cosby tweeted (via The Hollywood Reporter), "I have never changed my stance nor my story. I have always maintained my innocence. Thank you to all my fans, supporters and friends who stood by me through this ordeal."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Though it's become a rite of passage for a "Real Housewives" show to have a star with legal issues — see, for example, the dramatic circumstances surrounding "Salt Lake City" star Jen Shah and "Beverly Hills" housewife Erika Jayne — "Real Housewives of New Jersey" star Teresa Giudice was the first to go to jail over her crimes. She was sentenced to 15 months in prison after pleading guilty to multiple counts of fraud, though she claimed she didn't know what she was signing when she put her signature on fraudulent financial documents. "I've had sleepless nights. Of course, I was shocked. ... It was very unexpected. I don't even know what to say," she told Andy Cohen (via The Daily Dish).

Jonathan D. Larsen, the IRS agent in charge of the investigation, said in a press release on the day of her sentencing, "Reality hit home today for Giuseppe and Teresa Giudice. They are now both convicted felons with prison sentences to serve."

Though she reported to prison in January 2015, Teresa was out in time for Christmas (via People), ultimately serving only 11 months of her 15-month sentence. The table-flipping reality star disputed the idea that she had received preferential treatment while serving her time, telling "Good Morning America," "I mean, there was mold in the bathrooms. There was not running water constantly. The showers were freezing cold. It was hell. It was definitely living in hell."

After numerous run-ins with the law throughout the '90s, troubled actor Robert Downey Jr. told a judge that he was committed to getting sober despite repeatedly violating a previous court order to submit to regular drug testing. "It's like I've got a shotgun in my mouth, my finger on the trigger and I like the taste of gun metal," he said, describing why he had repeatedly failed to comply with orders to get clean. Per the Los Angeles Times, he was sentenced to three years in prison in an attempt to make sure he got sober.

He was released less than a year later after an appeals court noted that the sentencing judge failed to clarify whether his penalties would be served consecutively or concurrently, per CNN. Deputy Attorney General Jeffrey B. Kahan told the Los Angeles Times, "People talk about [how] you get loose on a technicality. This is one of those."

Marvel took a chance on the actor when it handed him the titular role in 2008's "Iron Man," and the rest is mega-budget franchise history. In an interview with Vanity Fair about his previous crimes and struggle with addiction, Downey Jr. said, "​​Job one is get out of that cave. A lot of people do get out but don't change. So the thing is to get out and recognize the significance of that aggressive denial of your fate, come through the crucible forged into a stronger metal. Or whatever."

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).

At the age of 16, before the Calvin Klein ads and the action movies, Mark Wahlberg committed some serious, racially-motivated crimes. According to The Smoking Gun, Wahlberg harassed a group of Black children and beat a Vietnamese man. Documents related to his arrest show that, in addition to using racist slurs against his victims, he told police officers, "You don't have to let him identify me, I'll tell you now that's the motherf***er whose head I split open." Per the Daily Mail, Wahlberg was sentenced to two years in prison, but he served only 45 days for his crime.

Wahlberg told ABC News that he no longer feels bad about what he did. "I did a lot of things that I regretted and I certainly paid for my mistakes. You have to go and ask for forgiveness and it wasn't until I really started doing good and doing right, by other people as well as myself, that I really started to feel that guilt go away," he said. 

However, Johnny Trinh, the Vietnamese man whom the actor assaulted, told the Daily Mail he never knew his attacker was Mark Wahlberg, indicating that Wahlberg hadn't reached out to him. Still, Trinh publicly forgave Wahlberg, supporting his efforts to seek a pardon. "He was young and reckless but I forgive him now," Trinh said. "Everyone deserves another chance." He also clarified that, despite reports suggesting Wahlberg was at fault, he was not blinded in the attack but had already lost his sight.

Though he was later found liable in a civil court for causing the death of Nicole Brown Simpson and Ron Goldman, we all know OJ Simpson avoided jail time for that incident, managing to be found not guilty of murder. However, he was later arrested on numerous charges relating to the theft of his sports memorabilia. Simpson claimed he was simply taking back what was already his, but the police disagreed; when the Associated Press (via CNBC) asked him why he hadn't called the cops to get the items back if they were really his, Simpson said, "The police, since my trouble, have not worked out for me." Thirteen years after he was acquitted of murder, Simpson was sentenced to 33 years in prison, per Reuters. "I didn't mean to hurt anybody, and I didn't mean to steal anything," he said. 

Ron Goldman's father was happy with the sentence, even though it was unrelated to his son's death. "We are thrilled, and it's a bittersweet moment. It was satisfying seeing him in shackles like he belongs," he told NBC News.

Nine years later, Simpson was released on parole, per AP News. "Please, can I have a break here? ... God bless, take care," Simpson said when he was surprised by a news camera hours after his late-night release. However, Simpson has not shied away from the public eye in the years since, commenting regularly on news stories on Twitter.

Rapper Meek Mill was "in and out of" the Philadelphia court system for more than a decade because of charges related to gun possession back in 2008, according to Rolling Stone. After numerous appearances in front of Judge Genece Brinkley, she sentenced him in 2017 to 2-4 years in prison for probation violations, against the advice of prosecutors. The arbitrary nature of the sentencing drew widespread condemnation; As CNN noted, his "violations" included things like riding a motorcycle without a helmet and popping wheelies, not typically the sort of thing one would be sentenced to serious jail time for.

Numerous hip-hop stars spoke out in his favor and called for his release, including Jay-Z. In the documentary "Free Meek," Jay said (via The Atlantic) that Mill's story represented more than just the one situation and in fact spoke to something seriously wrong with the legal system. "Meek is not the only one," he said. "You tell people these stories—you can't believe it, until you hear it from a source and [then] it's like, this is not fantasy. This is fact."

Ultimately, CNN reported that Mill was released five months into his 2-4 year sentence, thanks to an order from the Pennsylvania Supreme Court. "While the past five months have been a nightmare, the prayers, visits, calls, letters and rallies have helped me stay positive," the rapper said in a statement. Mill and Jay-Z have since launched a criminal justice reform organization together.

Paris Hilton has quite the resume: hotel heiress, reality television pioneer, actor in underrated films like "House of Wax," and singer behind the modern classic pop song "Stars Are Blind." (Not to mention her sex tape). In the late 2000s, though, at the height of her cultural power, she added another moniker to her multi-hyphenate resumé: jailbird.

Like fellow It girls Nicole Richie and Lindsay Lohan, Paris ran afoul of the law thanks to her hard-partying lifestyle finally catching up to her. She was arrested in 2006 on suspicion of drunk driving, and as a result, she lost her license. The following year, though, she was arrested once more, this time for continuing to drive on said suspended license — which she claimed not to realize had happened. "From now on I want to pay complete attention to everything," Paris told the court. That wasn't a good enough excuse, and the starlet was sentenced to 45 days in lockup, per Reuters. Her mother, future "Real Housewives of Beverly Hills" star Kathy Hilton, reportedly shouted, "You're pathetic!" at the judge who decided to lock Paris up.

However, Paris ultimately served only five days in prison before being released. According to the East Bay Times, the decision to move Paris from prison to house arrest was due to a medical issue, the specifics of which were not disclosed publicly.

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).

"Desperate Housewives" star Felicity Huffman was arrested in 2019 when she was caught up in the so-called College Admissions Scandal. She was accused of paying $15,000 to have a proctor help her daughter cheat on the SAT by giving her more time to take the test and fixing incorrect answers before it was submitted. Huffman pled guilty and admitted in a statement (via NBC News), "I am ashamed of the pain I have caused my daughter, my family, my friends, my colleagues and the educational community."

She was sentenced to 13 days in jail for the offense, and shortly after she began her sentence, photos showed the Academy Award nominee strolling around the prison yard in a green jumpsuit. USA Today reported that she ultimately served 11 days of her two-week sentence. It seems that a simple processing routine is responsible for her early release; for prisoners whose sentences would have been up on a weekend, the jail where Huffman was incarcerated lets people out on a Friday instead. That's nice!

Huffman has kept a low profile since her time in lockup. A source told E! News, "She is incredibly relieved that she has served her jail time and is moving ahead with her life."

Though he has since turned his image around and become a director, philanthropist, and an Academy Award-winning actor, back in the 1980s, a young Sean Penn was a bad boy prone to violent, headline-spawning outbursts. The tabloid fixture was even arrested in Macau in 1986 for holding a photographer out over a balcony on the ninth floor of a hotel, and he told a biographer that he and his assistant escaped from jail (via the Sydney Morning Herald). 

In 1987, Penn ran into his biggest legal trouble yet. Following a string of dangerous and violent incidents, including reckless driving and beating an extra on the set of "Colors" so badly that the man landed in the hospital, the Los Angeles Times reported that Penn had been sentenced to 60 days in prison.

He only served 32 days of his sentence before being released, with the Associated Press reporting that he had been let out for good behavior. Penn revealed decades later in a conversation with The Hollywood Reporter that he corresponded with fellow inmate Richard Ramirez, the serial killer known as "The Night Stalker," while in jail. An officer told Penn that Ramirez was a fan; after receiving a note from the Night Stalker that included a pentagram and a sketch of Satan, Penn wrote a reply reading, "'You know, Richard, it's impossible to be incarcerated and not feel a certain kinship with your fellow inmates. Well, Richard, I've done the impossible, I feel absolutely no kinship with you.'"

Of all the aughts-era socialites who went to jail in the 2000s, Nicole Richie got off easiest. In 2006, the star of "The Simple Life" was arrested on suspicion of driving under the influence of drugs after her car was reported to be traveling the wrong direction on a freeway. When cops arrived, her Mercedes-Benz was fully stopped in the carpool lane. California Highway Patrol Sgt. Mark Garrett told the Los Angeles Times that Nicole admitted she had taken Vicodin and smoked marijuana before getting in the car, a combination that apparently led to her disorientation.

While a previous arrest for possession of heroin had led to a court-mandated rehab stay, this time Nicole was sentenced to hard time. She pled guilty to charges of driving under the influence of drugs, and the judge decided she needed to repay her debt to society by spending four days in jail, per AP (via Action News 5.)

However, Nicole lucked out: because of serious overcrowding, she was ultimately only made to serve 82 minutes of her sentence. An L.A. County Sheriffs Department spokesperson told The Hollywood Reporter simply, "She was processed into the jail system, she was highly cooperative and she was released." Easy enough!

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).