Celebrity Prison Stories

No matter how you slice it, going to jail is inevitably going to be a humbling experience, especially when your every move is splashed across the tabloids. These celebs have done some time in the slammer, but no matter the crime, the circumstance, or length of time behind bars, each star has managed to walk away with an incredible story to share. From forming unlikely friendships to having odd moments of clarity, here's how the likes of Lindsay Lohan, Kiefer Sutherland, and more celebrities passed the time while incarcerated.

Martha Stewart spent part of her five months in federal prison exactly as you might expect: making arts and crafts. According to The New York Times (via The Herald News) Stewart revealed in 2016 that she passed the time by doing everything from making jam to ceramic nativity sets.

"You're allowed to make three things in a year, I think, and I only had five months so I made an entire creche ... the entire scene of the nativity," said Stewart, who was imprisoned for her alleged involvement in an insider trading scandal. Speaking to a crowd at a brunch event, she added, "So I had many figures, something like 15 figures, and you're only allowed to make three, but I persuaded them the whole nativity was one and they fell for it. You couldn't just make three camels — you had to make everything."

But life behind bars wasn't entirely wine and roses. Speaking to the Today show in 2013, Stewart — who was also sentenced to more than five months of home arrest — described her prison time as "terrible." She told then-anchor Matt Lauer, "It's hard to say, 'Good comes out of a bad time.' And that saying that, 'It only makes you better'? Oh my gosh. Bull. It's terrible. I lost a fortune."

Life inside federal prison was gross beyond words, according to a 2016 prison memoir released by The Real Housewives of New Jersey star Teresa Giudice. She served 11 months for conspiracy and bankruptcy fraud charges and supposedly dealt with everything from strip searches to inmate-on-inmate action, writing (via People), "The ladies were getting it on so much that our room became known as the Boom Boom Room."

In a separate interview with People, Giudice alleged that the food at her prison had gone bad. "Everything was expired. In the summer it got around that someone saw maggots in the rice, and that blew around the camp quick," she said. "I was grossed-out and never wanted to eat rice again but at the same time I was starting to cut out the carbs so it kind of worked anyway." Giudice added, "I had like a lot of stomach problems there. I couldn't go to the bathroom I was, like, dying. I was like, 'My stomach is killing me.' I started not eating so much of the meat because I would get sick. The meat I didn't eat because I knew it was definitely expired."

Ja Rule (real name Jeffrey Atkins) spent two years behind bars on gun possession and tax evasion charges. While in prison, he made the unlikeliest of friends by way of former politician Alan Hevesi and disgraced CEO Dennis Kozlowski. 

"Outside, you don't meet guys like this every day. This place is amazing," Rule told the New York Daily News while he was still incarcerated in 2012. The three inmates reportedly bonded over card games, basketball, and television, among other things. Rule also said Kozlowski, whom he nicknamed "Koz," supported the rapper's education goals: "I was studying for my GED and Koz came in and talked to me and said, 'if you need any help, let me know.'"

Ja Rule also discussed his stint in prison with talk show host Wendy Williams. "When I got there, people actually had a lot of admiration for me; a lot of love for me," he said. Well, when you make such classic '90s songs like "Livin' it Up," what's not to love?

Rapper Lil Wayne (real name Dwayne Michael Carter, Jr.) spent eight months in prison for a gun possession charge in 2010. During his stint, he kept a journal of his life behind bars, which he later turned into a memoir called Gone 'Til November. In the book, Wayne discusses everything from visits with psychiatrists to fights with inmates, and that time he recorded a rap for Drake over the phone.

"Who knew that my spirit was about to be lifted through the roof! [My manager] Tez was like, 'We want you to be on Drake's remix.' I was like, 'How?' And he was like, 'We're going to do it over the phone.' I'm like, 'S**t ... I don't have anything else better to do up in this b**ch, so let's go!” Wayne writes (via Vulture). "After I finished running it, I was kinda nervous on how it was going to be received. This was the first time that I haven't been in the studio to hear the playback before a song goes out."

He continues, "I can't front, I'm really bugging out knowing that I can record a song AND it would be on the radio and everything. My main thought is, Damn...if I can do this, I'm about to go to the studio every night ... Nothing can touch how happy I am. My creativity is at an all-time high right now! I'm actually looking forward to tomorrow."

Despite spending almost a year in jail for federal perjury charges, rapper Lil' Kim (real name Kimberly Denise Jones) managed to find the sunny side of a rather dark situation. 

"When I first got to prison, I slept so good for the first three weeks," she told MTV News in 2011. "I was working that whole two months before, nonstop, trying to finish an album, doing promo, doing [a] TV show, doing shows, doing all types of things. So I never slept, never [rested] at all for two months straight ... When I got there, I kind of just collapsed."

She said she was "greeted with open arms by a lot of wonderful, wonderful girls" at the prison, many with whom she remains friends. Lil' Kim also revealed that she received support from none other than talk show icon Oprah Winfrey. "She sent me three of her favorite books and said, 'Read these for inspiration and motivation,'" Kim explained. "She wrote me a letter in each book and just was like, 'Kim, you have so much potential. You're a very bright young girl.'"

Lindsay Lohan's seemingly never-ending legal drama was a PR nightmare for the Mean Girls star. And yet, even in her darkest moments (when she was sent to prison for violating her probation in 2010), she managed to find a bit of solace in the situation. 

While appearing on The Jonathan Ross Show in 2014, Lohan recalled the 14 days she spent in solitary confinement to protect her from the other inmates. "The weirdest part was, for me, I finally had silence in my life," the former child starlet explained. "As terrified as I was, and as scared as I was, I finally felt like I didn't have to answer to anyone. I didn't have to do anything for anyone. That was the weirdest part of it." Still, Lohan confessed that two weeks of solitary proved to be a bit much, saying, "Two days would have been enough."

In December 2007, Kiefer Sutherland was sentenced to 48 days in prison following his fourth DUI arrest over the course of two decades. The Lost Boys actor has since regretted the actions that led to his incarceration, telling People in 2016, "One of the things I love to do is go out with my friends and tell stories and have a bunch of drinks. Having said that, I can also look back on my life and tell you very squarely that the only bad things that have ever happened to me in my life have been because I like to go to bars and have drinks with my friends." 

However, he did admit to late night host David Letterman that finding humor in certain situations helped him move past the embarrassing nightmare of being imprisoned. "I was uniquely aware of where I was," Sutherland said on the The Late Show. "I remember in the second day, third day, I was in the showers, and ... I actually dropped the soap. And I remember looking down at the soap and looking around and went, 'Soap is overrated.' And, 'I'm done with my shower.'"

Paris Hilton's time behind bars was arguably as dramatic as the probation violation that sent her behind bars in the first place. Perhaps because of all the drama, once she was actually incarcerated, the heiress found herself humble and grateful for the freedoms she temporarily lost. Speaking from prison to radio host Ryan Seacrest in 2007, Hilton told stories about fan mail, supportive inmates, and experiencing a wide range of emotions. Ultimately, she said she felt God had put her there for a reason.

"I just feel that my life was going really fast. And there are so many people that look up to you. And the craziness of it all, sort of living in a superficial world," Hilton said (via E! News). "Now that I've been here and I've been seeing life through different eyes — just getting letters from all around the world — I have a lot of compassion for things that are going on around me that are so much more important than things I ever thought about."

Hilton continued, "I'm so much more grateful for everything that I have, even just to have a pillow at night or food or anything. My gratitude has gone up so much and I just realize that the media used me to make fun of and be mean about. I'm frankly sick of it. I want to use my fame in a good way."

Since his first film roles in the 1980s, Sean Penn has been universally regarded as one of finest actors of his generation. He also earned a reputation as a hothead prone to fits of rage and violence. After he attacked an extra for taking his picture on the set of Colors, he was sentenced to 60 days in jail in 1987 (via the Los Angeles Times). The troubled actor ultimately spent about a month behind bars — but it was an eventful one. Penn's cell was situated across from that of Richard Ramirez, the serial killer known as the "Night Stalker," who was eventually convicted and sentenced to death for 13 murders.

"After about a month of seeing each other around, he wanted my autograph," Penn told The Hollywood Reporter in 2015. Ramirez asked a deputy to get it for him, but Penn refused, saying, "I didn't trust the deputy because I'd gotten in some trouble inside there and just passing a piece of paper is contraband." Penn requested that Ramirez write him first, and then he'd write back. "So, I get this thing from him and it says, 'Hey, Sean, stay tough and hit them again — Richard Ramirez, 666,' with a pentagram and a rendition of the devil." Penn did respond then, writing back, "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."

To think that Bill Cosby was once known as "America's dad," thanks to his role as father-of-five Cliff Huxtable on The Cosby Show, his family-oriented stand-up comedy, and his bestselling books like Fatherhood. Allegations of sexual misconduct dogged Cosby for years, with more than 50 women speaking out about disturbing encounters with the comedian, with many claiming to have been drugged and assaulted. In April 2018, Cosby was found guilty of three counts of sexual assault against college basketball coach Andrea Constand during a retrial. According to CNN, Cosby earned a prison sentence of three to 10 years in the Pennsylvania prison system.

Now in his eighties, with vision problems and less than ambulatory, Cosby calls the SCI-Phoenix facility home. In 2019, Cosby gave a phone interview to BlackPressUSA, detailing how he passes the time. Cosby frequently speaks at weekly meetings of an African-American prisoner rehabilitation group called Mann Up, and personally counsels inmates about how to improve their lives and make better choices upon release. "I'm looking at a state that has a huge number of prisons," Cosby said. "And the one I'm in, thankfully, has the largest population of African Americans."

After entertaining millions with his fist-pumping, clubbing, and carousing on MTV's Jersey Shore, Mike "The Situation" Sorrentino went to federal prison. According to NBC News, he earned a sentence of eight months for a tax evasion charge. Sorrentino did his time at the Otisville Correctional Facility in southern New York, per Inquisitr, from January to September 2019 ... and he wasn't the only high-profile inmate there. The reality star paid his debt to society at the same time as President Donald Trump's former attorney, Michael Cohen, who was serving a three-year term for tax fraud and making false statements to a bank regarding hush payments he made on behalf of his boss.

Shortly after Cohen arrived, Sorrentino apparently approached him with a proposal. "I heard he didn't eat chicken. So I went straight up to Michael Cohen and I was like, 'Listen Mike. I'm going to need you to do something for me," Sorrentino alleged on Jersey Shore: Family Vacation (via People). "I'm going to need you to smuggle chicken for me, out of the main line." But when "chicken day" arrived, Cohen didn't deliver as he'd promised, reportedly explaining that the guards got wise. "He was like, 'Yo man, they know we tryin' to smuggle chicken,'" Sorrentino claimed.

Cohen's representative denied Sorrentino's claims to Page Six, calling it "red sauce self promotional fiction," whatever that means.

Thanks to his role as Tony Stark, a.k.a. Iron Man, in the extremely successful Marvel Cinematic Universe saga, Robert Downey Jr. is one of the most recognizable and well-liked movie stars in the world. That represents a remarkable turnaround for Downey, who fought a crippling drug addiction. In 1996, he was arrested for driving under the influence and possession of cocaine and heroin, and while out on bail, he wandered into a neighbor's house and fell asleep, which earned him three years' probation with a court-ordered rehab stint and regular drug testing. When he missed a test, a judge sentenced Downey to six months in the Los Angeles County Jail, and by 2000, he was in the middle of a three-year sentence at the California Substance Abuse Treatment Facility and State Prison, according to Vanity Fair.

Downey's job in the institution: kitchen worker. From 4:30 p.m. to 8 p.m., five nights a week, the actor served food and washed dishes. It was mostly dealing with industrial-size pots and pans, but on Thanksgiving, things went awry. A massive bag of premixed gravy, intended to feed dozens of inmates, exploded in the kitchen, and the task of cleaning it up fell to the former Weird Science star. "Thirty-three gallons of garbage water," Downey recalled to Vanity Fair. "Like 500 pounds of slop. It is at these moments — these points of acceptance — that you realize that human beings can do f**king anything."

Apart from the famous "conjugal visit" trailers, prison isn't a place much associated with consensual romantic encounters between men and women. After all, incarceration is essentially a punishment, and inmates are denied as many pleasures of the outside world as possible. But Mike Tyson, the heavyweight boxing champion of the world, found a way to make jail — where he served a stint in the early '90s for a rape charge — work for him. 

Behind bars, Tyson enrolled in a drug counseling system, even though he didn't do drugs, because it would "get time taken off your sentence," he wrote in his memoir, Undisputed Truth. After a few days in the class, Tyson developed a crush on his teacher, and arranged for the woman, a single mother with a collapsed roof at home, to receive $10,000. The next day, she began allowing Tyson to, well, romance her, repeatedly, for a long stretch of time. "She'd be calling me back three times a day," Tyson wrote, adding, "I was having so much sex that I was too tired to even go to the gym and work out."