Diddy is in jail and, shockingly, he isn’t having a good time. He apparently isn’t eating because he’s afraid he’ll be poisoned and, even worse, he’s stuck near Crypto douchebag Sam Bankman-Fried.
While the controversial hip-hop mogul may be struggling with his new life behind bars, perhaps he could learn from his fellow celebrities. After all, so many of our biggest and brightest stars have spent time in prison, too. And so, to help Diddy out, we compiled a roundup of celebrity prison stories that came directly from people who were in jail with them.
Of course, it’s important to remember that this is all coming from Reddit and Quora so it should be taken with a grain of salt. But it’s still pretty fascinating to think about…
Mike Tyson
In 1992, the undisputed heavyweight champ was sentenced to prison for raping an 18-year-old and was assigned to the Indiana Youth Center (now the Plainfield Correctional Facility). Someone who claimed to be there at the same time said that even though there were “much bigger guys” in the prison, everyone was smart enough to avoid messing with the Baddest Man on the Planet.
“Nobody.... and I mean nobody tried him,” he wrote.
Tyson’s fellow inmate also shared that despite Iron Mike’s terrifying demeanor, he was “friendly” and “had a few guys he got tight with.” His upbeat attitude may have come from the fact that he “had it a lot better in there then everyone” else and “could go pretty much anywhere.”
Robert Downey Jr.
It can be easy to forget that before he was winning Oscars and making approximately a bajillion dollars per movie, Robert Downey Jr. seemed like he had thrown away his career after landing in prison for a plethora of drug charges.
But even at his lowest point, the future Iron Man was still a nice, likable guy. At least, according to someone who allegedly was at CDC Corcoran prison at the same time. The anonymous jailbird said that Downey “was treated good by other inmates” and “had fans on the yard and a million stories.”
“I don’t know how many other celebrities would have been brave enough to walk the mainline, I think he earned a bit of respect for it,” he wrote.
In case you don’t know, the “main line” refers to the general prison population.
O.J. Simpson
Sean McGrath says he was in prison at the same time as the Juice and tells an absolutely amazing story about Simpson’s undying love for desserts even when he was behind bars.
According to McGrath, Simpson was playing softball when he spotted someone carrying cake. He quickly ran over and got himself a piece with the same ferocity that earned him a 2,000-yard season. “He scampered right through the middle of that game, straight across the yard,” McGrath shared. “That man was not going to miss out on some sheet-pan cake.”
Simpson was also a real-life Cookie Monster, often sneaking cookies out of the cafeteria by hiding them in his sleeves. Outside of guards letting him enjoy his sweet treats, McGrath says Simpson was “treated pretty much the same as everyone else.”
“There were small things he could get away with sometimes, like having more people in his cell than was allowed,” McGrath wrote. “Small things like that, but not all the time.”
James Brown
A 50-something-year-old accountant ended up getting sent to jail for “cooking the books” and was having a tough time dealing with his new reality. So, on his first day, he breaks down and starts crying in his cell. Suddenly, his cellmate walks up to him, slaps him in the face and tells him to shut the fuck up and man up.
That cellmate? None other than James Brown, who spent two years in jail after he was convicted of carrying an unlicensed pistol and assaulting a police officer, along with various drug-related and driving offenses.
Suge Knight
The accountant’s time in jail turned out to be incredibly star-studded, as he was also behind bars at the same time as Diddy’s good buddy Suge Knight. He even “ended up giving him tax/business advice,” which paid off because Knight thanked him by giving him a TV and “other stuff” in his cell.
Given the timeline, this was presumably during Knight’s four-year prison stint when he organized an attack on Orlando Anderson, who has been connected to the death of Tupac Shakur, not his current 28-year sentence.
DMX
DMX spent a year in prison in Yuma, and during that time, he’d allegedly occasionally participate in freestyle rap battles and, predictably, the professional MC would make everyone else look like fools.
“On Friday nights the … convicts would have freestyle battles in their bathroom, and sometimes X would go in there and school them,” says a person who was in prison with DMX. “If you’ve ever heard an amateur try to freestyle then imagine a professional rapper of his caliber going and showing why he’s one of the best.”
Jared Fogle
A guy said he was in the same prison as the dude who went from beloved pants holder to despised pedophile. There wasn’t much here, but according to the fellow inmate, Fogle was mostly treated okay except for when he was beaten up by some other inmates (hopefully, this happened a lot. Like, maybe every day or so?).
Ike Turner
Imagine being sent to prison and you decide to spend your time at the library. So you head over, only to find Ike Turner working there. That’s exactly what happened to one guy who says that Turner was “treated with respect by other inmates. Though his reputation with women remained … not great.
“My sister-in-law Gloria Scott was one of the Ikettes at one time,” the guy wrote. “When I told Ike this, he wanted me to give him her address. When I told my wife to ask Gloria if she wanted him to have her address, she said, ‘Hell no,’” because he was “a real prick towards all of the girls.”
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