Going to prison is inevitably going to be a humbling experience, especially when your
every move is splashed across the tabloids.
No matter the crime, the circumstances, or the length of time behind bars, these stars
managed to walk away with some rather illuminating prison tales.
As you may recall, Stewart was imprisoned in 2004 for her alleged involvement in an
insider trading scandal.
She spent some of her five months in federal prison doing exactly what you'd expect: Making
arts and crafts.
In 2016, she revealed that she passed the time in prison by making everything from jam
to ceramic nativity sets.
Addressing the crowd at a Daily Mail brunch, she reportedly said,
"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...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 that's not to say life behind bars was a walk in the park for Stewart.
Speaking to the Today show in 2013, she described her prison time as "terrible," telling then-anchor
Matt Lauer,
"It's hard to say good comes out of a bad time."
"Really?"
"Yeah and that saying, 'It only makes you better.'
Oh my gosh, I mean…"
"Bull?"
Lindsay Lohan's seemingly never-ending legal drama was undoubtedly a PR nightmare for the
Mean Girls star.
Yet even 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 former child starlet explained:
"The weirdest part was, for me, I finally had silence in my life.
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 for her.
"Two days would have been enough."
"Yeah.
And yet 14 days in there."
"Yeah."
Ja Rule 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.
While incarcerated in 2012, Rule told The New York Times,
"Outside, you don't meet guys like this every day.
This place is amazing."
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.
He explained,
"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."
"Yeah."
"So it was a really different experience."
Well, unless you happened to buy tickets to the FYRE Festival, what's not to love?
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 clearly regrets the whole situation 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, and that's true."
He goes on to say,
"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 the situation
helped him move past it.
As he put it,
"I was uniquely aware of where I was.
I remember on 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.'"
After actor Sean Penn reportedly attacked an extra for taking his picture on the set
of Colors, he was sentenced to 60 days in jail in 1987.
The troubled actor ultimately spent about a month behind bars, but it sounds like it
was a rather eventful month.
Penn's cell was reportedly right 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.
Penn told The Hollywood Reporter in 2015,
"After about a month of seeing each other around, he wanted my autograph...I get this
[note] from him and it says, 'Hey Penn, stay tough and hit them again.'
Richard Ramirez, 666, with a pentagram and a rendition of the devil...So I wrote him.
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."
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.
Sounds like it was good for him!
"When I went into prison, I was already very grateful.
I was on a great road mentally and spiritually.
But I had the time to work on everything else."
"Wow."
Sorrentino reportedly did his time at the Otisville Correctional Facility in southern
New York from January to September 2019...and he wasn't the only high-profile inmate there.
The reality star evidently paid his debt to society at the same time as President Donald
Trump's former attorney, Michael Cohen.
As you probably know, Cohen was theoretically serving a three-year term at the time for
tax fraud and making false statements to a bank.
Well, in a subsequent episode of Jersey Shore: Family Vacation, Sorrentino told the tale
of his encounter with Cohen:
"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.
I'm going to need you to smuggle chicken for me, out of the main line."
But when "chicken day" arrived, Cohen apparently didn't deliver as promised, reportedly explaining
that the guards had gotten wise to this remarkable scheme.
Sorrentino claims that,
"He was like, 'Yo man, they know we tryin' to smuggle chicken.'"
Cohen's representative denied all this funny business to Page Six, saying that,
"[These allegations are] red sauce self promotional fiction."
Whatever that even means.
Rapper Lil Wayne 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 fighting with
inmates, and that time he recorded a rap for Drake over the phone.
He writes:
"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---...I don't have anything else better to do up in this b----, so let's go!”
Of course, he was quite nervous about whether or not people were going to like the remix,
since he couldn't actually be in the studio to hear the finished production before it
came out.
As he explains it,
"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."
Hey, whatever works.
Robert Downey Jr. is one of the most recognizable and well-liked movie stars in the world…but
back in 1996, he was arrested for driving under the influence and possession of cocaine
and heroin.
It's not something he necessarily wants to talk about these days.
"I'm sorry, I really don't, what are we doing?"
"I, I, I, well, I'm just…asking questions."
"Right.
Bye!"
While out on bail, he reportedly 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.
After 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.
While there, Downey worked in the kitchen.
From 4:30 p.m. to 8 p.m., five nights a week, the actor served food and washed dishes.
He was mostly dealing with industrial-size pots and pans, but on Thanksgiving, things
apparently went awry: A massive bag of premixed gravy, intended to feed dozens of inmates,
exploded in the kitchen, and he was given the unenviable task of cleaning it up.
As he told Vanity Fair,
"[It was] thirty-three gallons of garbage water.
Like 500 pounds of slop.
It is at these moments, these points of acceptance, that you realize that human beings can do
f---ing anything."
Despite spending almost a year in jail for federal perjury charges, rapper Lil' Kim still
managed to find the bright side.
She told MTV News in 2011,
"When I first got to prison, I slept so good for the first three weeks.
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."
Sounds like she also made some good friends there, too.
"I really met good people."
"Yeah?"
"A lot of the smartest people are in prison."
Lil' Kim also revealed that she received support from talk-show icon Oprah Winfrey, explaining
that,
"She sent me three of her favorite books and said, 'Read these for inspiration and motivation.
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."
Here's a question: Did you ever curl up with a copy of Turning the Tables?
It's the 2016 prison memoir written by The Real Housewives of New Jersey star Teresa
Giudice.
Inside, she claims that life in federal prison is basically too gross for words.
"I went to jail.
Like, yeah of course I'm angry."
While serving 11 months for conspiracy and bankruptcy fraud charges, Guidice supposedly
dealt with everything from strip searches to inmate-on-inmate action.
As she told People magazine,
"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 claimed the food at her prison was literally
rotten.
She said that,
"Everything was expired.
In the summer it got around that someone saw maggots in the rice, and that blew around
the camp quick.
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...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."
Could time in jail have changed Paris Hilton for the better?
That was the story she tried to tell Ryan Seacrest in 2007 while serving time for violating
her probation.
Speaking from prison, she told tall tales about fan mail and emotionally supportive
inmates.
Ultimately, she seemed to think God put her there for a reason, explaining that:
"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.
Now that I've been here and I've been seeing life through different eyes...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 did her best to portray herself as a newly sympathetic and humble person, and
we'll let you decide just how successful she was.
Hilton went on to tell Seacrest,
"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."
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