TV and Movie Gangsters Played by Real-Life Criminals

Getting real-life gangsters to play pretend ones on TV and in movies adds a layer of authenticity you can’t get any other way. It draws in audiences eager to see the real thing, and often, these “button pushers” already have the right look and attitude without needing to do one bit of acting or research.

Actors who were bona fide criminals before stepping into the limelight also bring a level of intensity to their roles that can only come from living the life. Their performances have left a lasting mark on both the big and small screens, and these are some of the most memorable examples of fictional gangsters played by the genuine article.

Lenny McLean was an English boxer known to many as "The Guv'nor." According to his own autobiography, he was also an enforcer in London's criminal underground, which is a nicer way of saying some people may or may not be dead, and McLean may or may not have had something to do with that, wink wink. 

Later on, he became an actor, lending a thuggish authenticity to the proceedings that no amount of method acting can bring. 

He’s best known to cinephiles for playing Barry the Baptist in Guy Ritchie's “Lock, Stock and Two Smoking Barrels,” but sadly, he passed away before the film’s release.

Danny Trejo has been acting since he appeared in “Runaway Train” in 1985. Since then, he’s played countless convicts, ex-convicts, drug dealers, and gangsters until finally earning the starring role as Machete in 2010 in the extremely violent movie of the same name. 

Prior to all that, he spent over a decade in maximum-security prisons, so if he seems like the real deal, that’s because he is. 

Now 80 years old, he has found himself embraced by mainstream audiences, appearing in commercials for Snickers bars and eventually joining the “Star Wars” franchise by appearing in “The Book of Boba Fett” as a kindly Rancor keeper who teaches us all that what the terrifying creature really needs is just love.

Michael Franzese was affiliated with the Colombo crime family and was sentenced to a decade in prison after pleading guilty to federal racketeering and tax conspiracy charges. He was eventually released in 1994 and retired to California to become a motivational speaker, which some may consider a worse crime than racketeering. 

In 2019, the man known as “The Yuppie Don” appeared in “Let There Be Light,” which was directed by and stars Kevin Sorbo and also features the acting work of journalist Sean Hannity. Franzese plays a character named “Pastor Vinny,” a mobster-turned-clergyman, who tells the story of Jesus Christ’s crucifixion and resurrection thusly – “Jesus got whacked, badda boom. Then the body disappeared.”

Speaking of Michael Franzese, he also indirectly figures into the story of one of the most beloved mafia movies of all time, “The Godfather.” Lenny Montana is one of the best-known former gangsters in the world thanks to his appearance in the movie as lovable doofus Luca Brasi, and according to Franzese, Montana was "one of us," which is to say that he too was affiliated with the Colombo crime family. He added that behind the scenes, Montana also had a hand in approving both the script and the casting.

Tony Sirico played Peter Paul “Paulie Walnuts” Gualtieri on HBO’s beloved crime series “The Sopranos.” While he was in a supporting role, he stole every single scene he was in. Born in Brooklyn, he was arrested 28 times and went to prison twice, losing almost three years of his life to the penal system. Rather than hide his criminal past, he used what he learned to great effect and told Larry King in an interview that he had no problem being typecast as a gangster. “I have been in over 40 films and God knows how many TV shows, and I have had a gun in my hand in most of them,” he said. “But, I don’t feel bad about it, Larry. I pay the rent and mortgage.”

Former Hell’s Angel Chuck Zito played a convict on the gritty HBO prison drama “Oz.” He brought a lot of experience to the role, as he spent 1985 through 1991 in prison on drug charges, and the show’s executive producer, Tom Fontana, told the New York Times that the former outlaw biker brought “authority and credibility” to the portrayal. In 2004, after “Oz” ended, Zito quit the Hell’s Angels to focus on acting full-time.

Alex Rocco played the pivotal role of Moe Greene in "The Godfather," in which he had some of the best lines ("I made my bones when you were going out with cheerleaders!") and one of the most shocking demises. He also “did a little time in the Billerica House of Correction,” per WCVB in Boston. He was arrested three times for his activities as a bookie and even served jail time for a brawl, but he resolved to leave the criminal life behind and become an actor instead. Good man.

Michael Squicciarini was only on “The Sopranos” very briefly in its second season, but he was hard to miss. At almost six and a half feet tall and 300 pounds, his hulking frame made him an ideal casting choice for anyone who needed intimidating-looking goons in their organized crime movie or television show. Sadly, he passed away in 2001 before he could create a career for himself as an actor, but the story doesn’t end there. In 2002, he was posthumously implicated in a 1992 gangland execution after witnesses recognized him from episodes of “The Sopranos” shown to them by police.

Tony Darrow was the stage name of Anthony Borgese, and if you like movies and television shows about organized crime, you’ve probably seen him, as he appears in both “Goodfellas” and “The Sopranos.” While many of the fine thespians on our list were involved in organized crime activities before they started acting, Darrow was already an actor in 2011 when he pleaded guilty to extortion charges related to a 2004 assault of a man who owed money to the Gambino family.

In Quentin Tarantino’s 1992 directorial debut “Reservoir Dogs,” one of the members of a crew whose heist goes wrong is Mr. Blue, played by Edward Bunker. He spent most of his teenage years getting into trouble with the law and going in and out of reform schools and foster homes, culminating in him stabbing a guard at a juvenile detention center and then escaping from Los Angeles County jail. He was sent to the infamous San Quentin State Prison, becoming its youngest inmate at age 17. Rather than succumb to unproductive worry, he wrote the crime thriller “No Beast So Fierce” while he was locked up, and after his release, he stayed out of prison for the rest of his life.

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