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Actors love to talk about authenticity, but if that were all it took, we wouldn’t need them at all — cops, lawyers, and singles on the prowl could just play themselves (space aliens and superheroes, maybe not so much). There’s more to it than that, of course, but sometimes it doesn’t hurt to have a background in the role being played. Many former Marines have done well as actors, using their discipline for our entertainment. And as it turns out, many thespians with actual criminal records do a great job of playing crooks onscreen. As 2024’s Oscar-nominated film “Sing Sing” depicts, theater programs can serve as therapy, and serve to reform offenders.
Throughout the history of the movie business, real-life criminals have found the movie business to be more comfortable than their former under-the-table careers. Audiences, in turn, can often tell when a guy onscreen really looks like he could kill or beat you. In some cases, showbiz saved their lives and kept them off the streets, but in at least one, it didn’t serve as deterrence at all.
Having said that, here are 10 of the best real-life criminals who made a better name for themselves by also playing criminals in movies and/or on TV.
George Raft
The gangster villain of “Some Like It Hot” was a former boxer and professional dancer, but what people remember most about his extra-curricular activities were his mob ties. A childhood friend of Bugsy Siegel, he befriended other criminals during his nightclub dancing career and worked as a driver for some of them. Following an affair with a married woman, however, he moved from New York to Los Angeles, and he ended up playing made men rather than fully becoming one.
Raft didn’t consider himself much of an actor, but he was charismatic enough to make it work by being himself in front of the camera. In his major break, in Howard Hawks’ 1932 “Scarface,” he compensated for his relative lack of lines by constantly flipping a coin, creating a trope that would outlast him. Batman villain Two-Face (a role Clint Eastwood almost played) may be the most notable example today.
Though he often played criminals, Raft turned down a number of roles because he didn’t want to always play a bad guy. This led to a career pause in the 1950s, but when he came back, it was with “Some Like It Hot,” which paid tribute to his “Scarface” role, and “Ocean’s 11.” Investigated for tax evasion in the ’40s, he was convicted and fined in 1965. He became part-owner of a London casino in 1966, but after visiting the U.S, he was denied re-entry because of his alleged underworld ties.
Crime boss Mickey Cohen once said Raft was the only actor he trusted to play him.
Danny Trejo
Admit it, when you first read the headline on this article, Danny Trejo was the first person who came to mind. The distinctive character actor, and now purveyor of donuts and vegetarian tacos, is one of Hollywood’s most visible examples of turning one’s life around. A drug dealer, heroin addict, and debt collector, Trejo found religion and kicked the habit in 1968 following a stint in solitary confinement. After his release, he was doing some work as an extra when he was recognized by former fellow inmate-turned-screenwriter Edward Bunker (see next item below). Bunker got him a job training Eric Roberts to box for the movie “Runaway Train,” which he followed with “Bulletproof,” “Penitentiary III,” “The Hidden,” and “Death Wish 4.”
Trejo has had over 200 acting roles since, saying he’d rather work and make money than just stay home and spend it. He’s appeared in everything from big-budget action flicks like Michael Mann’s acclaimed “Heat” to direct-to-video exploitation fare like “Alone in the Dark II.” Against type, he appeared as Uncle Machete in the “Spy Kids” films, playing the tech-savvy “Q”-type in the franchise. Director Robert Rodriguez later twisted the character a bit to make him an exploitation hero in a fake trailer within the movie “Grindhouse,” which spawned two R-rated “Machete” films, and there might be a third set in outer space, but we’re still waiting.
Rodriguez eventually got him to the stars, specifically “Star Wars,” as a rancor keeper in “The Book of Boba Fett.”
Edward Bunker
Bunker’s biggest cinematic legacy may be that he remembered watching Danny Trejo box in San Quentin and got him hired to his first major film gig, but he’s not without significant credits of his own.
In 1950, at the age of 17, he became the youngest inmate in San Quentin history, and while in prison, developed a love of books. Over 20 years and multiple stints in the big house later, he published his first novel, 1973’s “No Beast So Fierce.” Dustin Hoffman acquired the movie rights, and he originally planned to direct the movie himself but was replaced with Ulu Grosbard when the studio felt he was working much too slowly. Retitled “Straight Time,” it featured a screenplay co-written by Bunker, who got to appear in a small role. (Michael Mann also did a pass on the script, which informed his later work.) Bunker continued to play small roles in movies like ‘Tango & Cash,” “Miracle Mile,” and “Reservoir Dogs,” usually playing criminals.
Edward Bunker’s books will probably remain his primary claim to fame, rather than his acting, but he also adapted his novel “Animal Factory” into a movie directed by Steve Buscemi, starring Willem Dafoe, Edward Furlong, Mickey Rourke, Seymour Cassel, and his old pal Danny Trejo. Yet between 1978 and 2010, he appeared in 24 movies. Not bad for a guy who was in his mid-40s when he got his first on-camera role.
Vinnie Jones
A particularly violent soccer player from England, once caught grabbing an opponent right in the junk, Vinnie Jones was finally convicted of assault in 1998, after attacking his neighbor. That also happened to be the year his first film — “Lock, Stock, and Two Smoking Barrels” — came out. Jones continued to work with director Guy Ritchie,playing the terrifying Bullet-Tooth Tony in “Snatch,” and Hollywood promptly took notice as well, casting Jones in “Gone in 60 Seconds.” In arguably the most perfect casting of all, Jones starred in a UK remake of “The Longest Yard” called “Mean Machine,” in which he plays an imprisoned and violent soccer player who coaches a team of convicts to play the wardens.
Fame didn’t quite soothe the savage beast, as he was arrested again in 2003 for a drunken air rage incident in which he threatened, among other things, to eat a fellow passenger’s face. This caused him to lose the right to own weapons, although he has continued to wield them onscreen in movies with names like “Gutshot Straight” and “I Am Vengeance: Retaliation.” However, he has also learned to show a softer side since, sending up his tough-guy image in family films like ‘Garfield: A Tale of Two Kitties.”
Though he played Juggernaut in “X-Men: The Last Stand,” “Deadpool & Wolverine” didn’t have the budget to pay for him to cameo on top of all the other big names, so that’s a different actor in his old costume.
Clarence ‘Divine Eye’ Maclin
It’s possible that one of the reasons Colman Domingo didn’t win the Oscar for Best Actor this year for his performance in “Sing Song” is that he was thoroughly upstaged by his costar, who wasn’t even nominated for Best Supporting Actor. “Divine Eye” comes across onscreen as a very real, very dangerous prison inmate, and it’s not merely as an actor playing one. It turns out he’s both.
Sentenced to 17 years in prison for robbery, Clarence Maclin signed up for Rehabilitation Through the Arts at Sing Sing prison, where he learned acting and credits it for transforming his life. For the movie ‘Sing Sing,” about the program, actual graduates were brought in to play major roles alongside Domingo and Paul Raci. “Divine Eye” was given the option of creating a fictional character or playing a version of himself with his real name, and he chose the latter. In scenes with the veteran Domingo, he more than holds his own.
Maclin also helped compose the screen story, and he won several acting awards, including the Gotham Award for Outstanding Supporting Performance. He continues to work as a youth counselor, but he has lined up his next major project: the movie “In Starland” from British actor-turned-director Ray Panthaki (“EastEnders”).
Curtis ’50 Cent’ Jackson
It might be easy to list rappers turned actors who have some kind of criminal record, but it’s safe to say most of them were cast more for their fame in music videos than their real-world misdeeds. In the case of Curtis Jackson, better known as 50 Cent, however, he was specifically cast to play the younger, criminal version of himself (here renamed “Marcus”) in the semi-biopic “Get Rich or Die Tryin.'”
Inspired by the success of Eminem’s “8 Mile” and loosely based on Jackson’s life and produced by Interscope Records’ head Jimmy Iovine, the film was directed by Jim Sheridan, who was hot off the critically acclaimed success of “In America” about the plight of Irish immigrants. Sheridan proclaimed himself a longtime fan of rap music, and he hoped that Jackson’s stoic face would remind viewers of John Wayne. It didn’t work out quite that way.
“Get Rich or Die Tryin” was a box-office dud, screenwriter Terence Winter complained it was nothing like what he wrote, and Sheridan acknowledged that Jackson was no John Wayne. However, he got better: The rapper has consistently appeared in movies ever since, playing cops, crooks, and even himself in another box office bomb, the hilarious “Popstar: Never Stop Never Stopping.” Most recently, he appeared in “Den of Thieves 2: Pantera,” reprising his role from the first film.
He also clearly still loves “8 Mile,” as he’s developing a TV show based on the Eminem movie.
Charles S. Dutton
Sent to jail for five years for manslaughter, three for robbery and firearms charges, and eight more for punching a guard, Charles S. Dutton brought a book of Black playwrights into solitary confinement, and thereafter, he sought permission to create a prison drama group, which was approved on condition he get his GED. After his release, he went on to get a BA and a master’s degree in drama, and he made his Broadway debut in 1984.
Dutton’s first breakthrough movie role used both his education and street smarts to his advantage. In “Crocodile Dundee II,” he plays Leroy Brown, who pretends to be a tough hustler but actually sells stationery. For his next major role, “Alien3,” he played a convicted rapist and murderer who found religion while confined to a prison planet.
He got even more notice on TV with the sitcom “Roc,” featuring three of his fellow regular Broadway costars: Ella Joyce, Rocky Carroll, and Carl Gordon. Loosely autobiographical, it used Dutton’s old nickname for its title, short for “rock head,” because kids in his neighborhood used to have rock-throwing fights, and he’d often get busted open. Though the show only lasted three seasons, it was notable for doing most of the second season live. Dutton blamed the lackluster ratings on Fox’s lack of promotion, though he rarely wanted for work thereafter.
Dutton also went on to direct, including one of Meg Ryan’s last major films, “Against the Ropes.” Now retired, he lives on a farm on Maryland.
Mark Wahlberg
When Mark Wahlberg first started acting, he became famous as the clean rapper Marky Mark, known for goofily dropping his pants onstage and being the brother of New Kids on the Block’s Donnie Wahlberg. His actual background was darker, having served 45 days of prison time for assaulting a Vietnamese-American man while high on PCP, as well as assaulting a Black neighbor, for which he settled out of court. As a teenager, he’d already been served with a civil injunction for attacking Black children while yelling epithets. His early movie roles as a delinquent in “The Basketball Diaries” and a psychotic stalker in “Fear” clearly drew on his illegal side, rather than his image as the white guy rapping over Lou Reed’s “Walk on the Wild Side.”
His major breakthrough role as porn star Dirk Diggler in “Boogie Nights” successfully drew both sides of his persona together, turning him into the sex symbol and the criminal in a part inspired by the late John Holmes (for which he asked God’s forgiveness). From there, he became an A-lister, with lead roles in the likes of “Three Kings,” “The Perfect Storm,” and Tim Burton’s “Planet of the Apes,” among plenty other great movies in his career.
In more recent years, Wahlberg has more strongly affirmed his Catholic faith, and he teamed up with the equally zealous Catholic Mel Gibson, who has also been accused of racial epithets and battery, for “Father Stu” and “Flight Risk.” Wahlberg has also hinted that he might be retiring soon.
Lawrence Tierney
Unlike many on this list, Lawrence Tierney was technically an actor first, spotted by an RKO talent scout while doing theater. Before he could make a name for himself in the movies, though, he began accumulating a criminal record, mostly due to being a violent drunk. Tierney assaulted cab drivers, musicians, and cops, and he even did time in a mental institution. In the 1940s, however, this wasn’t necessarily a career killer, and he became a star for playing notorious bank robber John Dillinger in 1945’s “Dillinger.” It led to many more roles as crooks and tough guys, particularly in the film noir genre.
By the ’50s, his brushes with the law became a career problem, though he continued to make TV guest appearances and get smaller parts in movies. Following a move to France, he made a bit of a comeback in the ’70s and much more of one in the ’80s, when he moved to L.A. and frequently got TV guest spots. However, many of the regular cast members who worked with him, like Jerry Seinfeld and Wil Wheaton, found that working with him once was enough. In 1991, he scored the major role of Joe Cabot in “Reservoir Dogs,” but after trying to shoot his own nephew and getting into a fight with Quentin Tarantino, he was fired after a week. Former Marine Harvey Keitel had to step in to make peace and ensure Tierney finished the movie.
Tierney died 11 years later, in 2002.
Nathan Jones
The nearly seven-foot tall Australian Nathan Jones did seven years in a maximum security prison for his role in eight armed robberies. Upon release, the muscular giant promptly became a powerlifting and arm wrestling champion. That led him to his first movie role as a Russian hitman in Jackie Chan’s “First Strike,” but rather than immediately following it with more, he went into MMA and pro-wrestling instead. Heavily promoted in WWE with an ex-con gimmick and the nickname “The Colossus of Boggo Road,” he largely proved to be a washout, frequently no-showing, missing his major WrestleMania XIX match for unclear reasons, and ultimately quitting because he found the touring schedule too rough.
Fortunately for him, there’s plenty of room in Hollywood for a giant muscleman who knows how to play to camera and make fighting moves look good. He returned to the big screen to fight Brad Pitt in “Troy,” battled his former WWE coworker Steve Austin as a fellow prisoner in “The Condemned,’ and he most recently appeared as the wasteland outlaw heir Rictus Erectus, son of Immortan Joe, in “Mad Max: Fury Road” and “Furiosa: A Mad Max Saga.” In his next role, he’s set to appear in Marshall Thurber’s live-action adaptation of ‘Voltron,” for Amazon-MGM Studios.
