Celebs Who Met In Prison
While it's rare, there have been remarkable instances where celebrities have actually met each other during their time behind bars. This phenomenon offers a fascinating glimpse into the lives of the rich and famous when they find themselves in less than glamorous circumstances. For instance, although Snoop Dogg and Martha Stewart did not meet in prison, their individual experiences with incarceration have become a notable part of their public personas. Stewart spent five months in a federal prison in Alderson, West Virginia, from 2004 until 2005 after being convicted for insider trading (via History Channel), and Snoop has famously spent a lot of time behind bars after numerous arrests.
The duo first met on an episode of Stewart's television show "Martha" back in 2008, and friendship sparks flew, with the homemaking guru later saying on an "Ask Me Anything" on Reddit, "I wish I were closer friends with Snoop Dogg" (via People). Stewart got her wish — in 2016, they took their buddy status to TV with VH1's "Martha & Snoop's Potluck Dinner Party," which ran for three seasons. And Snoop and Stewart aren't the only celebrities who connected because of prison ... take a look at all the stars who met each other behind bars.
Jen Shah and Elizabeth Holmes
"The Real Housewives of Salt Lake City" star Jen Shah pled guilty to conspiracy to commit wire fraud in connection with telemarketing and conspiracy to commit money laundering back in November 2022. The reality star received a six-year prison sentence in January 2023 and reported to Bryan Federal Prison Camp the following month. While doing time behind bars, she ended up making friends with another famous face – disgraced Theranos founder Elizabeth Holmes. Holmes, whose scandalous story was fictionalized on the Hulu series, "The Dropout," reported to the same institution a few months later that May to start her 11-year sentence on fraud charges.
Shah's representative, Chris Giovanni, opened up about the unlikely friendship to People, revealing, "They're friends. They're both rehabilitating and have bonded over being on this journey of positive change. Their situations brought them together, and they have a good understanding of one another. They're getting through it together." He revealed that Holmes frequents workout classes taught by Shah in the prison, reportedly called "Sha-mazing Abs," explaining, "Jen gets all the ladies together and they rally behind her while she teaches them fitness moves, and Elizabeth has been there right along with them." Giovanni also remarked that both ladies have "changed a lot behind bars."
Billy McFarland and Mike The Situation Sorrentino
Speaking of Hulu, if you caught their documentary "Fyre Fraud," then you'll recognize this next man. Billy McFarland was one of the masterminds behind the infamous 2017 failed music festival, which resulted in the fraudster being sentenced to six years in prison in 2018 for conning both investors and customers out of over $26 million. Though he only served four of those in federal prison, during his time behind bars, he met another famous face — Mike "The Situation" Sorrentino of "Jersey Shore" fame. Both men crossed paths while serving time in New York's Otisville Federal Correctional Institution, with Sorrentino doing eight months for a tax evasion conviction.
In the midst of Sorrentino's prison sentence, his co-stars, Pauly DelVecchio and Vinny Guadagino, revealed the odd pairing, sharing on "The Jenny McCarthy Show" in April 2019, "He is in there with the guy from the Fyre Festival ... They play Scrabble together!" Once Sorrentino was released, Sorrentino downplayed their relationship, telling co-star Nicole Polizzi on her podcast, "It's Happening with Snooki and Joey," "He would say 'Hi,' but he wasn't in my group of friends. I played against him in basketball and softball maybe, but then he was thrown out of the prison" (via Fox News).
Mike The Situation and Michael Cohen
Another famous face Mike "The Situation" Sorrentino met during his time at New York's Otisville Federal Correctional Institution? Former President Donald Trump's former lawyer, Michael Cohen, who was there serving three years for tax evasion, lying to Congress, and campaign finance crimes. Once Sorrentino was released, he spoke openly about his time behind bars and his impression of Cohen on an episode of his MTV reality series, "Jersey Shore Family Vacation," revealing that he worked out an arrangement with the attorney (via People). "A lot of the guys will barter, they'll make deals for food. So when Michael Cohen came in to prison, 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.'" It turned out, Sorrentino's arrangement for extra protein didn't end up working out, as he shared, "Thursday comes around, which is chicken day — Cohen is nowhere to be found. I was like, 'Damn, Cohen was chicken on chicken day!'"
For his part, Cohen's representative shot down Sorrentino's prison food story, telling Page Six it was a "red sauce self promotional fiction."
Todd Chrisley and Rick Singer
Former "Chrisley Knows Best" star Todd Chrisley found himself behind bars at FPC Pensacola in Florida following his 2022 conviction on bank fraud and tax evasion, arriving to start his 12-year sentence in January 2023. Once an inmate, the reality star found himself face-to-face with another infamous figure, Rick Singer. The same month Chrisley reported to prison, Singer was sentenced to nearly four years in prison after being convicted of racketeering conspiracy, money laundering conspiracy, conspiracy to defraud the US government, and obstruction of justice in the wake of the college admissions scandal, referred to as the "Varsity Blues" scandal, that involved several notable names, including Lori Loughlin and Felicity Huffman.
Chrisley's daughter Savannah Chrisley revealed that her father and Singer know each other at the Florida prison. While appearing on Nick Viall's "The Viall Files" podcast in September 2023, Savannah shared, "The Varsity Blues guy that was the whole ringleader of Lori Loughlin's thing ... He like came up to dad and told dad he was writing a book, and dad was like, 'Make sure you don't leave out the chapter where you snitched on everyone.'" Though Savannah made it clear that Singer and her father aren't exactly best buddies, she did note her dad is like "the president of this place," who has been making plenty of friends behind bars.
Ja Rule and Alan Hevesi
Rapper Ja Rule was sentenced to two years in prison back in 2011 following a 2007 incident where police found a semi-automatic gun in his car. He reported to Brooklyn's Metropolitan Detention Center to serve his sentence, where he ended up rubbing elbows with the former New York State Controller, Alan Hevesi. Hevesi had been sentenced to one to four years in prison in 2011 following his involvement in a scandal with state pension funds, and reported to the same prison as Ja Rule that April.
Ja Rule discussed the unlikely friendship while speaking to The Daily News behind bars in 2012, sharing, "Outside, you don't meet guys like this every day. This place is amazing" (via Today). He revealed that his nickname for Hevesi was actually "Hevey D." Ja Rule would later tell Complex in his first post-prison interview in 2013 that he and Hevesi bonded over a certain sports team, saying, "Me and Alan, he's a Knicks fan like me, so we watched a lot of Knicks together, never missed a game." Aside from sports, they also talked about current events, with Ja Rule noting, "We talked politics. The election was going on while I was locked up, Obama and Romney, so we would talk a lot about that. Hevesi is a Democrat so we were on the same side."
Sean Penn and Richard Ramirez
Esteemed actor Sean Penn has spent time behind bars. Back in 1987, he was sentenced to 60 days in jail for charges stemming from both reckless driving and punching someone on the set of his film. When he was placed in a Los Angeles County jail, he happened to find himself in the company of one of the most iconic serial killers of all time, Richard Ramirez. Known as "The Night Stalker," Ramirez had a lengthy rap sheet, all of which led to him crossing paths with Penn in the '80s.
Penn later reminisced about his eerie encounter with Ramirez while speaking to The Hollywood Reporter, sharing, "He wrote me [a letter] ... After about a month of seeing each other around, he wanted my autograph." Penn was wary of getting in trouble for passing paper and asked Ramirez to send something first. According to Penn, that led to him receiving a note that read, "'Hey, Sean, stay tough and hit them again — Richard Ramirez, 666,' with a pentagram and a rendition of the devil." In response, Penn revealed that he wrote back, "'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. And I hope gas descends upon you before sanity does, you know? It would be a kinder way out.' And they gave it to him. And then my house burned down years later, and that damn thing of his burned with it."