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9 celebrities who spent time in jail before they were famous

By / 02.16.13
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Celebrities in Jail Before Famous

ToddABishop, Flickr


Famous people are always doing dumb stuff that gets them tossed behind bars. At some point, I guess you figure the laws of planet Earth no longer apply to you and so you start walking out of stores with diamond bracelets or driving down the freeway even though you just mainlined Jack Daniels all night long because...well, hell, you don’t need a reason. You’re famous! But while everybody knows about the Lindsays and Mels and Charlies and OJs of the word, not everybody knows about those precious few celebrities who find fame and fortune even after seeing the inside of a jail cell. And so without further ado, here are nine celebrities who spent time in jail before becoming famous.

Photo credit: ToddABishop, Flickr

Danny Trejo

cmjcool, Flickr


Long before Danny Trejo gained notoriety as a Hollywood badass he earned notoriety of a different sort -– that of a hardened criminal. Trejo spent parts of 11 years in jail and prison after getting caught up in drugs and armed robbery. Eventually, while in the famous San Quentin, Trejo took up boxing and became a prison champ. After getting clean, Trejo made the right connections and the rest is history. Charlie Sheen can rant and rave all about tiger blood all he wants and Mel Gibson can get away with extorting blowjobs in exchange for a promise not to commit arson but I’m guessing if either one of those assholes ever stepped to Danny Trejo they’d spend the rest of their lives sipping their meals through a straw and asking his permission every time they wanted to take a piss. In a land of fake badasses, Danny Trejo is the real deal and he has the record of a hardened prison badass to back it up.

Photo credit: cmjcool, Flickr

Stephen Fry

Marco Raaphorst, Flickr


A British Renaissance man, Stephen Fry has found fame and fortune as an actor, comedian, novelist and journalist, which is a hell of a feat when you consider that Fry got his adult life off on the wrong foot after getting thrown in jail for swiping a credit card from a family friend. Fry spent three months in prison, but rather than succumbing to a life as a petty criminal, Fry saw the error of his ways, enrolled in school, studied his ass off and gained admittance to Cambridge where he met Hugh Laurie, who would go on to be his collaborator and co-star in the pairing which brought both men their first tastes of fame. Naturally, the lesson to be learned from all this is that credit card theft will eventually lead to fame and fortune. Wait... right? No? Well, I see no logical flaws in that line of thinking. None at all. Well, I guess there is the downside of, you know, spending time in prison, but it seems like it worked out okay for Stephen Fry. I’m just saying.

Photo credit: Marco Raaphorst, Flickr


It turns out that the star of Roc is actually a crazy badass. Who knew? Well, I’m guessing the dude Dutton stabbed to death in a street fight when he was 17 figured that out pretty damn quickly -- which saw Dutton land in prison for manslaughter for several years -- as did the prison guard he beat down while incarcerated during yet another prison sentence, this time for possessing a deadly weapon. Damn. Dutton served almost five years for that beat down and during that time, Roc apparently discovered a love of drama. Well, why not? I mean, up until that point his whole life had been nothing but drama. Since then, Dutton has carved out a nice career as a character actor, highlighted by his appearance in the third Alien film and his star turn as the titular character of the aforementioned Roc. I’m guessing that in real life that Alien would have run like hell once he found out that Roc wasn’t afraid to stab a mofo. Forget Alien vs. Predator. I want to see Alien vs. Roc.

Photo credit: YouTube/Roland Martin

Bill Gates

ToddABishop, Flickr


The details behind Bill Gates’ arrest are murky, but as you can see from the mugshot there, it did happen. It’s believed that Gates was arrested after being busted for reckless driving and driving without a license in New Mexico in 1977, and although I’m guessing that he probably only spent a few hours in a holding cell before being released, it wasn’t the first time that Wild Bill was busted by the law for driving like a bat out of hell. Reports indicate that he was also arrested in New Mexico in April of 1975, and there are some reports that indicate that he was arrested again one time after that. The whole thing is strange as hell, and who knows what actually happened? There is nothing but scattered reports and a tantalizing mug shot to suggest that Gates was terrorizing New Mexico roads throughout the mid to late ‘70s. No matter what went on there, what we do know is that Gates was arrested yet again in 1989 on suspicion of drunk driving charges. Goddamn, Wild Bill! Eventually that charge was reduced and Gates went on to become the uber-billionaire we all know and love.

Photo credit: ToddABishop, Flickr


Nick Nolte managed to avoid a long prison term but he is a convicted felon, having been busted for selling fake draft cards in 1962. Stuck with five years of probation after that fiasco, Nolte still isn’t allowed to vote and he has reportedly refused every invitation he has received to the White House because he feels like the president shouldn’t be hanging around with convicted felons. That brings up some interesting questions though. I mean, how often is Nick Nolte being invited to the White House? Isn’t that kind of weird? Or is that just part of an actor’s normal routine? 12:00 - lunch with my agent, 3:00 – poker with the President. Sure, I can see Nick Nolte and Bill Clinton getting along well, maybe trolling for ass in seedy DC bars, but the whole idea is just a little weird, right? Anyway, Nolte didn’t seem to be hurt too much by his conviction as he went on to become one of the biggest stars of the late-‘70s/early-‘80s. Oddly, though, he might be best known to the Internet generation for his infamous mug shot, taken after his DUI arrest in 2002.

Photo credit: YouTube/Backstage

50 Cent

Pop Culture Geek, Flickr


Before he was famous, 50 Cent was busted for selling crack and ended up doing time. But unlike most crack dealers, the man originally known as Curtis Jackson didn’t do time in a conventional prison. Instead, he was sent to a boot camp prison where he spent the next several months presumably exercising and getting screamed at, which I suppose is better than fighting off would be prison rapists. When he emerged, Jackson went clean, becoming an accountant and retiring to the suburbs. Wait, you mean that’s not what happened? Okay, fine. After leaving boot camp, Jackson changed his name to 50 Cent and became such a paragon of virtue that it led to him getting shot up in front of his grandma’s house. But all that did was add to the growing legend of 50 Cent and it all became part of an aura which –- along with his talent -- helped him become a big star.

Photo credit: Pop Culture Geek, Flickr


Robert Mitchum was a wild little dude, getting chucked out of school when he was 12 for fighting with the principal before eventually getting arrested for vagrancy when he was only 14. He was put on a chain gang (At 14!) before he supposedly escaped and found his way to California where after a series of odd jobs, he took up acting and became a big Hollywood star. Perhaps the archetype of the badass Hollywood rebel, Mitchum would eventually find himself busted in 1948 for smoking pot with a starlet named Lila Leeds, for which he received 60 days in jail but that was probably easy time compared to his chain gang days. Seriously, the dude was on a chain gang when he was 14. 14! I guess they just didn’t give a damn back in the Depression. Find an eighth grader on the street and chain his truant ass up. These days that would get you a visit from Chris Hansen. But for Robert Mitchum, it was just a part of his childhood development, and the start of a renowned life of badassery that would last until his death decades later.

Photo credit: Wikimedia Commons


Yes, long before he was the Tool Man, Tim Allen was a coke dealer. Busted at an airport with reportedly over a pound of cocaine(!), Allen faced a long prison sentence, but Allen saw the writing on the wall and volunteered to snitch on his cohorts which allowed him to get off with a comparatively light sentence. Still, Allen spent over two years in federal prison where I’m guessing he perfected his famed grunting techniques with the help of an overly amorous cellmate. Allen eventually fought his way to fame via his every man comedy routine, serving as the forefather for such luminaries as Jeff Foxworthy and Larry the Cable Guy, which, let’s be honest, is the greatest crime he could have ever committed. Seriously, shouldn’t that be a violation of his probation or something?

Photo credit: YouTube/ABC

Don King

Shawn Lea, Wikimedia Commons


I know it might surprise you, but Don King hasn’t always found himself on the right side of the law. Shocking, I know. Indeed, it would seem that in his early days, King was damn near a gangster. King was accused of a ton of crimes back in the day as the head of a Cleveland gambling operation, including the murder of a dude in 1954. Apparently, King shot the poor guy after he caught him breaking into his shop. Amazingly, the shooting was ruled self-defense and King went on being, well, Don King. In 1966, however, his luck ran out when he was again busted for getting all kill happy. It would seem that King got into a fight with an employee named Sam Garrett over money, naturally, and during the fight, Garrett hit his head on the pavement and was carried off by his spirit horse. Some believe that he was actually stomped to death by King and apparently it was all enough for King to finally get convicted of manslaughter. He served only four years thanks to some slick legal maneuvering before being released and making the fateful decision to abandon gambling for the cleaner world of professional boxing where he famously served as a pristine promoter and an excellent role model for a young boxer by the name of Mike Tyson. Ahem. Well, at least nobody got hurt. And by nobody I of course mean everybody.

Photo credit: Shawn Lea, Wikimedia Commons


(Previously published on April 7, 2011.)

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TAGS50 CentArbitrary RankingsBill Gatescelebrities who've been to jailcelebrities who've served timecelebsCharles S. DuttonDanny TrejoDon KingfeaturedListsNick NolteRobert MitchumStephen FryTim Allen
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