Can celebrities really manifest their dream roles through style choices?
The actor spent 11 years in and out of jail. In 1968, he was even accused of having started a prison riot. "We went to the hole and were facing the gas chamber, and I remember asking God, 'Let me die with dignity. Just let me say goodbye. And if you do, I will say your name every day, and I will do whatever I can for my fellow man,'" said Trejo.
But there's more. Trejo not only met the infamous Charles Manson while in prison in 1961, but he was also hypnotized by him. "If that white boy wasn’t a career criminal, he could have been a professional hypnotist," shared Trejo.
"It put me in a position of great humility, and I was able to make amends to friends and family and refocus my life on setting and achieving goals," the actor said about his time behind bars.
The actor was frequently in trouble with the law during the height of his addiction and ended up spending almost a year in prison. Robert Downey Jr. worked as a kitchen worker while incarcerated.
Though these classes turned out to be more personal than he initially thought. Tyson got romantically involved with the teacher. "She'd be calling me back three times a day," he wrote. "I was having so much s e x that I was too tired to even go to the gym and work out."
The former heavyweight boxing champion of the world served three years in prison in the 1990s. Tyson confessed in his autobiography that he enrolled in a drug counseling system just so he could get time taken off his sentence, even though he reportedly didn't do any drugs at the time.
The actor was arrested for drug trafficking and served almost two and a half years in prison in the late 1970s.
The actor recalled an episode on Thanksgiving, when a huge bag of premixed gravy exploded in the kitchen and he had to clean it. "Thirty-three gallons of garbage water," the actor recalled. "Like 500 pounds of slop. It is at these moments—these points of acceptance—that you realize that human beings can do f*****g anything," he said.
The famous actor spent 60 days in jail in 1987 for punching an extra on a movie set. Penn ended up in a cell situated opposite that of Richard Ramirez, a serial killer known as the "Night Stalker," with whom the actor ended up exchanging notes.
The 'Jersey Shore' star was sentenced to eight months in prison in 2018 for tax evasion. He shared his time with Donald Trump's former attorney, Michael Cohen, whom he allegedly tried to persuade to smuggle chicken for him!
Ramirez wanted Penn's autograph but the actor refused because he didn't trust the deputy, so he asked for the serial killer to write to him first. He did. Ramirez sent him a note with a pentagram and the devil that read, "Hey, Sean, stay tough and hit them again — Richard Ramirez, 666." Penn replied, "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."
The socialite spent some time behind bars for violating her probation, and Hilton is grateful for it. "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," she said. "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,."
It looks like incarceration was a humbling experience for Hilton. "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," she said.
In 2007, the actor spent 48 days in jail for DUI charges. Sutherland turned to humor to cope while being locked up. "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," he once said in an interview.
The actress went through a rough period and ended up being incarcerated for violating her probation in 2010. The 14 days Lohan spent in solitary confinement seemed to have helped her find solace. "The weirdest part was, for me, I finally had silence in my life," she confessed.
"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," Lohan added.
As for his time behind bars, Sutherland shared a peculiar episode: "I was uniquely aware of where I was. 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.'"
The rapper served a year in prison after she was charged with perjury. She'd been working nonstop until then, so it was like a blessing in disguise. "When I first got to prison, I slept so good for the first three weeks," she said.
The rapper might have spent eight months incarcerated for a gun possession charge in 2010, but the incident didn't slow down his career. Not only did he write the memoir 'Gone 'Til November,' but he even recorded a rap for Drake over the phone!
The rapper was locked up for two years for gun possession and tax evasion. Ja Rule was generally welcomed in prison and even made some unlikely friends, including former politician Alan Hevesi and Tyco CEO Dennis Kozlowski.
"Outside, you don't meet guys like this every day. This place is amazing," Ja Rule confessed. "When I got there, people actually had a lot of admiration for me; a lot of love for me."
Martha Stewart spent five months in prison after she was sentenced for allegedly being involved in an insider trading scandal in 2003. So how did she spend her time in prison? Making arts and crafts, of course!
This included making a whole nativity scene with ceramic figures. But life in prison was not just a workshop for Stewart. "'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," Stewart confessed.
"Life in prison was hell. People were dying every week. [But] I think it helped me to get to the point I'm at now. It gave me time to reflect, it made a lot of relationships that were toxic in my life just fall away," he confessed.
The rapper was incarcerated for two years in 2014, but made the most out of his time locked up to release music. But prison was not just a jolly creative time.
The actor served 45 days in prison for attempted murder in the late 1980s. "When I went to jail, that was a wake-up call. Over my lifetime I've known a lot of unsavory characters. I made a lot of mistakes in my own life, too, but thankfully, I was able to learn from them," he said.
"Although it has taken some adjustment, I cannot deny the favor I have encountered while in here, and general warm reception from a community of people who, despite their circumstances, have found unique ways to make the best of them," Hill said.
Not only did she have the chance to rest from her hectic work schedule, Lil' Kim was "greeted with open arms by a lot of wonderful, wonderful girls." But she also received lots of support form outside, including Oprah Winfrey, who sent her three books with a letter in each book.
Many celebrities have done prison time. And while some never opened up about their time behind bars, others have confessed what it was like to be incarcerated. From finding solace, to meeting some unlikely inmates, and even getting romantically involved, in this gallery you'll find a bit of everything.
Boris Becker is out of prison after serving just eight months of his 2.5 years sentence. The German tennis legend was found guilty of several bankruptcy offenses and sentenced in April 2022. In a March 29 interview with CNN’s Christiane Amanpour, Becker said he felt lucky to be alive after his incarceration. “Prison life is a very dangerous place," he admitted. "It’s very scary. It’s a real punishment." In a previous interview with German broadcaster Sat 1, Becker said that another inmate tried to kill him.
In discussing his survival strategy, he told Amanpour, “The only currency you have is your character and your personality – literally – and you better make friends with the strong boys because you need protection, you need a group of people that look out for you.”
Browse through the gallery and learn what prison was like for these celebrities.
Boris Becker
Celebs open up about their time in prison
Boris Becker opens up about "scary" life in prison after serving eight months
CELEBRITY Crime
Boris Becker is out of prison after serving just eight months of his 2.5 years sentence. The German tennis legend was found guilty of several bankruptcy offenses and sentenced in April 2022. In a March 29 interview with CNN’s Christiane Amanpour, Becker said he felt lucky to be alive after his incarceration. “Prison life is a very dangerous place," he admitted. "It’s very scary. It’s a real punishment." In a previous interview with German broadcaster Sat 1, Becker said that another inmate tried to kill him.
In discussing his survival strategy, he told Amanpour, “The only currency you have is your character and your personality – literally – and you better make friends with the strong boys because you need protection, you need a group of people that look out for you.”
Many celebrities have done prison time. And while some never opened up about their time behind bars, others have confessed what it was like to be incarcerated. From finding solace, to meeting some unlikely inmates, and even getting romantically involved, in this gallery you'll find a bit of everything.
Browse through the gallery and learn what prison was like for these celebrities.