7 Famous Celebrities That Had To Spent Time In Prison

Prison is a tough place for anyone, but some prisons are definitely rougher than others, but what is it like for celebrities in prison?

You wake up peacefully and begin your day without looking at social media. Instead, it’s straight to the gym to do your daily workout. After that, you’ll probably just spend the day reading and meditating.

No, we’re not describing a personal development retreat. We’re talking about a day in a cushy, low-security prison in the United States.

But this time, you’re not just another Tom, Dick, or Harry whose tragic turn of events in life led to them being locked away in a dangerous prison. Nope, now you’re an A-list prisoner convicted for a white-collar crime. That’s the name given to the non-violent crimes typically committed by the middle classes and other powerful individuals.


White-Collar crime and celebrities


In this case, you might be able to skip the orange overalls and the regimented daily routines. But don’t look too eager for your social media detox. Being rich and famous is no guarantee that you’ll have it easy on the inside. You’ll still need to eat gross food, work for a few cents an hour, and get by with minimum contact with your loved ones.

But it does mean you’ll have the resources to pay for a private prison consultant to help you fit in and keep your affairs in order whilst you’re away. If you don’t know what a prison consultant is, you’re either not middle class enough or not enough of a criminal.

Prison consultants help their clients to blend into prisons and avoid getting into trouble. Presumably, they offer stellar advice such as not dropping the soap. Sorry, we had to make that joke once, and you know it. Some of these consultants for the incarcerated ask for six-figure salaries.


How celebrities have fared in prison?

Martha Stewart

Martha Stewart, by Gage Skidmore, licensed under CC BY-SA 2.0 via Wikimedia Commons

Martha Stewart was a celebrity cook and domestic goddess. A businesswoman, a television personality, a writer – all the usual jazz. But she’s now also very well known for being found guilty of insider trading. Basically, she lied about the price of a stock. And if that’s not a shining example of white-collar crime, then I don’t know what is.

Stewart was sent to the Federal Prison Camp in Alderson, Western Virginia for five months, a minimum-security prison camp. As things go, she got a pretty good deal. Federal prison camps are where people who’ve been convicted for their first nonviolent crime get sent. They have the best on-site amenities and facilities. With classes in yoga, fitness, aerobics, cosmetology, and stress relief, Alderson was no exception.

Built in 1928, Alderson was the first federal prison for women in the US. The 159-acre minimum security grounds near Greenbrier State Forest contain cottages and unfenced grounds and the place follows principles of reformation. The jazz singer Billie Holiday was also a past inmate after getting arrested for drug possession.


After the morning count, inmates are free to wander the vast grounds as long as they sign out properly and return by 4 pm. Alternatively, they might choose to visit the television room, library, chapel, or education building, where they can pursue various apprenticeship programs.

Alderson Federal Prison Camp entrance, by Christopher Ziemnowicz, licensed under CC BY-SA 3.0 via Wikimedia Commons

The security in the institution is so low that one prisoner, Lynette Fromme, escaped.

By the looks of things, Martha’s time in Alderson was a breeze. She started yoga classes, which is possibly the most white-collar thing ever. And when she wasn’t practicing her downward dog, she was replying to emails from her fans – she received 15,000 of them in her first month alone. It must have been a tough way to pass the time.


But although her time there sounds cushy on paper, Stewart herself said that she found the experience horrifying and disturbing. Although it was a minimum-security prison, she still had to deal with guards and take part in hard labor.

Now for a prison that is possibly even posher than Alderson.

Felicity Huffman

Felicity Huffman, by Angela George, licensed under CC BY-SA 3.0 via Wikimedia Commons

You might have heard of Felicity Huffman. The actress became infamous in 2019 after paying a scammer to do some funny business and help her daughter get into a prestigious college. As a result, she was sent to prison.


The prison in question was the Federal Correctional Institution in Dublin, another institution viewed by many as being a cushy option. Located in the Bay Area of California, it’s known as Chateau Dublin. And you’re about to find out why.

If you thought yoga classes were extra, you haven’t heard anything yet. Chateau Dublin contains gardens, tennis courts, knitting classes, and meditation courses.

Inmates can wander around as they like, wear what they want, and they even have plenty of choice over what food they can order. In the private rooms of the inmates, they have access to television and internet access. Are we the only ones feeling cheated for slumming it when we could be living rent-free in a luxurious prison?


The cushy reputation of the place is so extreme that a warden who works there had to point out that it isn’t, in fact, a resort and prisoners go there to be punished. But honestly, the fact he even had to say that just makes me more suspicious.

When it comes to rich and powerful prisoners, you’d struggle to find someone with more status than a previous lawyer to the president. Michael Cohen was arrested in late 2018 after being found guilty of tax evasion, making false financial statements, and violations of campaign finance.

Michael Cohen

Michael Cohen, by The Circus, licensed under CC BY 3.0 via Wikimedia Commons

But Cohen saw the silver lining of the situation, claiming he’d already been living in personal and mental incarceration by working under Trump, so prison would bring back his freedom. That’s quite the dig.


He was placed in FCI Otisville near New York City, which is often viewed as a preferable prison for white-collar crimes. Forbes named it one of America’s cushiest prisons back in 2009.

Bernard Madoff specifically requested to be sent there after he admitted to running a criminal Ponzi scheme, but his request was sadly rejected.

The medium-security institution is made up of two parts: a detention center with stricter rules, and a satellite camp where life is good. Cohen was in the satellite camp.


To make sure the men there don’t get bored, there’s a wide range of recreational activities and sports to take part in. These include horseshoes, weights, bocce ball, a basketball court, a handball court, a tennis area, and a baseball field.

From the sounds of things, Cohen had the time of his life there. His attorney said he got a tan, lost more than 30 pounds, was able to destress, and even started writing a book.

He also got a nice job repairing fire hydrants, which was probably a lot less stressful than covering up the scandals of the President, and made plenty of friends. Turns out lots of the inmates were looking for some good legal advice and were also curious to know about Cohen’s experiences involving Trump and Stormy Daniels. He got the nickname Mr. Mayor in prison and was treated by many as a celebrity.

Michael Cohen in 2011, by IowaPolitics.com, licensed under CC BY-SA 2.0 via Wikimedia Commons

But no discussion of luxurious prisons would be complete without Ford Dix, a low-security federal prison often known as ‘Club Fed’ and one of the most famous white-collar prisons. Past inmates include Real Housewives of New Jersey cast member Joe Giudice and Martin Shkreli, who was arrested for the multimillion-dollar fraud involving hiking the price of an AIDS drug.

The low-security federal prison contains 4,000 inmates, who they trust to show responsibility. That means no bars, no towers, and no locks on rooms in community units.

Just like Cohen’s prison, FCI Otisville, there are plenty of sporting facilities on offer. Gym equipment, racquetball courts, volleyball, bocce ball lanes, pool tables, you name it. Oh, and you can also take part in hobby crafts or go to the music room.


Seriously though, what is it with the bocce ball? Since when did anyone under the age of seventy play this and why is it seemingly the sport of choice in male prisons?

Bill Cosby

Bill Cosby in 1965, by NBC Television, Public domain via Wikimedia Commons

As far as celebrities go, being the world’s highest-paid actor at one point in time is a pretty big flex. How would someone as famous as Bill Cosby fair in prison?

Cosby was arrested for drugging and sexually assaulting a woman. Obviously, this is a pretty serious crime, so the cushy minimum-security institutions weren’t going to cut it. Instead, he was sent to the Phoenix State Correctional Institution in Pennsylvania in 2018 – maximum-security prison.


But still, they wouldn’t just put him in any old maximum-security prison. The place Cosby was sent to is known as being the newest and most expensive prison in Pennsylvania – in fact, some call it state-of-the art.

But don’t get excited thinking this state-of-the-art prison is full of thought-provoking murals or cutting-edge architectural structures. Not quite. You’ll find barbed wire fences, walkways, and exercise yards.

As a bonus, Cosby was given the privilege of a private cell adjacent to the infirmary – the few cells like this are usually reserved for those with life sentences. But due to the attention they might attract, celebrities are usually given private rooms and a chance to settle in before they’re released to the general population.

Bill Cosby in 2011, by Bill Cosby, licensed under CC BY 2.0 via Wikimedia Commons

Cosby’s cell included a small metal bed, tiny metal closet, personal metal table, small metal toilet, and a sink made out of – yep, you guessed it – metal. So state-of-the art. The cell was also air-conditioned and he had the chance to buy a radio, tablet, and TV. All in all, it sounds pretty good.

There’s no evidence of tennis courts or games of bocce here, but there are a few perks. There are educational, vocational, and recreational programs, plus the opportunity to work or go to the gym.

Bizarrely, there have been rumors about Cosby getting into fights with other inmates, including one involving someone throwing a chicken patty or banana at his face. However, Cosby’s team has denied this – it must be nice to have someone taking care of your PR whilst you’re locked away.


Anyhow, it now seems like Cosby is having a good time. Apparently, he’s made a name for himself by making motivational speeches and has also lost a lot of weight.

Paris Hilton

Paris Hilton, by Office of Congressman Greg Steube, Public domain via Wikimedia Commons

But now let’s take a look at some celebrities who didn’t have it so easy, starting with none other than Paris Hilton.

Ah, Paris Hilton. She certainly had a wild decade in the noughties, the peak of which saw her


sent to jail in 2007 for 23 days after violating the probation for her DUI charge. What happened after that is kind of confusing and a bit of a mess.

First, Paris was sent to the Century Regional Detention Facility in Los Angeles. But due to an undisclosed medical condition that was probably mental health-related, she ended up being moved to monitored house arrest instead. For obvious reasons, this looked sort of bad, and the law enforcement didn’t want to be seen to go easy on a celebrity.

So, Paris was then asked to appear in court and moved back into jail. Madness. And then she ended up only serving half of her sentence anyway because of overcrowding in the prison and her good behavior. Talk about a rollercoaster ride!


Many say Paris was made an example of to show that celebrities aren’t above the law. So, maybe being a celebrity doesn’t always guarantee you a great time in prison. Who knew.

But she was able to see the bright side, saying that prison was an experience of self-actualization that helped her to gain more compassion. It also helped her secure plenty of post-jail interviews when she came out, which must have softened the blow.

Robert Downey Junior

Robert Downey Jr. in 2014, by Gage Skidmore, licensed under CC BY-SA 2.0 via Wikimedia Commons

And now for a guy who definitely served his time. He may have put it behind him now, but Robert Downey Junior has a rough history. He was arrested for substance abuse issues in his youth and sent to a Los Angeles jail for 113 days over 1997 and 1998.


Because of his sentence, Downey was sent to the California Substance Abuse Treatment Facility and State Prison, a minimum to moderate security center found in the middle of the dry Californian desert.

He might not have been staying in a particularly tough facility himself, but it was next door to a maximum-security prison that held Charles Manson at the time.

In an interview with Vanity Fair, Downing admitted feeling shocked to find out what the prison was like when he arrived in shackles and saw a guard’s tower. I’m sure having Vanity Fair turn up regularly to interview him did wonders for his street cred in prison, too.


Other cellmates often accused the staff of serving him bigger portions or tried to target him for his wealth, but he tried his best to fit in. He was so committed to just being one of the lads that he offered to sleep in the top bunk!

Suge Knight

Suge Knight in 2007, by Nick Leisure, licensed under CC BY-SA 2.0 via Wikimedia Commons

Another celebrity that had it tough is Suge Knight, the music executive and CEO of Death Row Records. Suge had plenty of altercations with the law but was arrested in connection with a hit-and-run death in 2015. As you can imagine, that didn’t exactly land him in the best prison in the country.

Knight was held in solitary confinement and banned from phone calls and visitors. He claimed law enforcement officers were listening in on his meetings with lawyers. But also, two of the 15 attorneys he hired were witness tampering, so are you surprised? And don’t even get me started on why he had that many attorneys in the first place.


Knight suffered ongoing health issues whilst he was locked up and blamed prison conditions. His son also claimed that prison staff were mistreating his father and trying to break his spirit. So, did he have it tough, or was he just a handful and trying to cheat his way out of prison?