Inside Celebrities’ Lives Behind Bars

Even Stewart’s time in a prison that was once described as “cushy” by Forbes was not a pleasant experience. In fact, the television personality, who was imprisoned for lying about the sale of a stock, called the experience “horrifying.”

“No one, no one, should have to go through that kind of indignity, really, except for murderers, and there are a few other categories. But no one should have to go through that. It’s a very, very awful thing,” Stewart said on Next Question with Katie Couric in 2017.

She continued, “There are lots and lots of disturbing things that go on in an incarceration like that. In minimum security you still couldn’t walk out the gate or cross the river. There’s still guards, and it’s still nasty.”

Real Housewives of New Jersey star Teresa Giudice, who spent time at FCI Danbury on fraud charges, echoed Stewart’s prison sentiments years later. She described the period as “living in hell” and says she worked for just 12 cents an hour in the kitchen.

“I mean, there was mold in the bathrooms. There was not running water constantly. The showers were freezing cold … I mean, the living conditions were really horrible. Like, horrible,” she alleged during a Good Morning America appearance. “There were some nights that we didn’t even have heat … It was hell.”

Chrisley confirmed there was no preferential treatment while he was locked up; in fact he experienced the opposite. During his time in prison, where he was incarcerated on charges of conspiracy to commit bank fraud, wire fraud and tax evasion, he claimed FPC Pensacola was “disgustingly filthy” and the food was inedible.  Although he attempted to buy a majority of his food from the commissary, Chrisley alleged a staff member limited the number of purchases he could make.

“The food is literally, I’m not exaggerating—the food is dated, and it’s out of date by, at minimum, a year,” Chrisley claimed on Chris Cuomo’s NewsNation show, Cuomo. “I’ve been told this by a staff member—one of the ways she’s trying to break me is by cutting down what you can buy in commissary. So, before she came [there]you could buy 12 packs of tuna a week. She cut it down to six, and from six it went to three. She had not given a reason—when I asked her about it, she said commissary is a privilege, not a right.”

Celebrities are generally safe in prison as long as they abide by the facilities’ rules and regulations. When Robert Downey Jr. was sent to the California Substance Abuse Treatment Facility and State Prison on drug charges in 1999, he called it the “safest place on Earth.”

“When the door clicks shut, then you are safe,” Downey told Rolling Stone. “There is nothing aside from a rogue correctional officer that can do you harm if you have the right cellie. You are actually in the safest place on Earth. Safe from the intruders. From anything that might thwart the mortal coil.”

However, high-profile prisoners do at times attract some unwanted extra attention. When Sean Penn was behind bars at Mono County Jail for assault, he had a close encounter with serial killer Richard Ramirez, who had sent him a note requesting an autograph.

“I said, ‘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,” Penn said during a Q&A at Loyola Marymount University.

Meanwhile, celebrities do occasionally get caught up in dangerous situations with other inmates or staff members. Chrisley alleged that he was subject to blackmail while behind bars, explaining that “there was a photograph taken of me while I was sleeping and sent to my daughter, asking for $2,600 a month for my protection.”

In response to the allegations, the Federal Bureau of Prisons said in a statement that it aims to “operate facilities that are safe, secure, and humane” and that “humane treatment of the men and women in our custody is a top priority.” Chrisley was pardoned and released in May 2025.