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11 Movie Mobsters We Idolize While We Shouldn’t

There’s no doubt that gangsters and mobsters are some of the most dangerous and cruel people out there and it’s a safe bet that not many decent people would look up to them in real life. Despite this fact, it’s really weird but also quite true that for some reason many movie gangsters, mobsters, and criminals have become some of the most iconic and admired characters in film history. Here follow 11 such “heroes” who have become some of our favorite movie characters for one reason or another.
Written by Theodoros II


Despite Michael being the main character, we pick Vito Corleone as our favorite gangster from Mario Puzo's novel The Godfather and its film adaptation. The role has been portrayed by Robert De Niro (as a younger man) and the one and only Marlon Brando in the first film of the trilogy. Premiere magazine named Vito Corleone the greatest movie character in history and we don’t think many can disagree with that. 


Tony Montana is legally to blame for possibly the most famous quote in the history of any gangster and Mafia film ever made, and of course I am referring to the epic “Say hello to my little friend!” Tony Montana (portrayed so convincingly by Al Pacino) has become a pop culture icon and is one of the most recognizable movie characters of all time, and in 2006 a video game called Scarface: The World Is Yours was developed by Radical Entertainment and published by Sierra Entertainment in honor of the film. 


“Lefty,” as Benjamin Ruggiero was known to Mafia circles, was a real person and a soldier in the Bonanno crime family. The masses got introduced to him, however, in the film Donnie Brasco where the mighty Al Pacino portrays “Lefty” in a way that makes him look more like a victim when in reality Ruggiero was responsible for the death of twenty-six people. 


Reservoir Dogs was one of the early and more awesome works of Quentin Tarantino when the famous director gave to the world many legendary characters without even trying as hard as he’s been trying recently. Even though we could easily select any gangster from this brilliant film we’re gonna stick with sadistic psychopath Mr. Blonde (portrayed by Michael Madsen) simply because we recently discovered that he was the brother of Vincent Vega (John Travolta) from Pulp Fiction which followed shortly after Reservoir Dogs. Be honest, did you know that? We sure didn’t. 


The most fascinating part of Tommy DeVito’s story—a role based on a gangster named Thomas Anthony “Two-Gun Tommy” DeSimone—is that Joe Pesci did not physically resemble the tall, muscular “Two-Gun Tommy” at all, who was only in his teens and twenties during the events depicted in Goodfellas. However, Pesci’s portrayal was between 90 and 95 percent accurate according to police reports and the people who knew the gangster and that should tell you something about Joe’s incredible acting skills, which certainly make up for his small stature. 


Carlito Brigante is a Puerto Rican ex-convict trying to make a decent living and stay out of trouble but a series of unfortunate circumstances and a bad social environment won’t let him do the right thing. Al Pacino takes the role to another level and portrays him as only he could—as one of the most sympathetic, charming, and humane gangsters in film history.


The real George Jung, whom Johnny Depp portrayed so accurately in Blow, was released from prison on June 2, 2014, after serving nearly twenty years for drug smuggling. As the movie clearly shows, Jung was a major player in the cocaine trade in the United States during the 1970s, and we must admit that never again has a gangster’s lifestyle resembled a rock star’s so much in both film and real life. 


Vincent Vega is not just another mobster but the role that resurrected John Travolta’s career and gave him an Academy Award nomination. Vincent is a hit man working for mob boss Marsellus Wallace (Ving Rhames) and looks-wise he resembles more a rockabilly music star a la Elvis than your typical Mafia man. Last but not least, he’s easily the greatest dancer-gangster in film history and his iconic dancing scene with Mia Wallace (Uma Thurman) is clear proof of this.  


Keyser Söze is probably the most mysterious, vicious, supernatural, and dark mobster in film history, at least according to his self-description or, to be more accurate, as described by his alter ego, Roger “Verbal” Kint. After all these years we’re still trying to figure out if he was a man or the devil himself. “And just like that . . . he’s gone.”


Sonny LoSpecchio is a character in 1993’s A Bronx Tale, which was directed by Robert De Niro, and was interpreted as the autobiographical story of the legendary Italian-American actor. As for Sonny? He’s doubtless one of the coolest and best-dressed gangsters in film and even though he wasn’t Calogero’s father, he’s the one who’s remembered as the caring father figure in the film.  


After a lifetime of hits, gang brawls, and petty thefts Big Chris gets “promoted” and is commissioned to go on a special assignment to find four gangster wannabes. Guy Richie once again pleasantly surprises us by hiring a retired footballer and certified badass, Vinnie Jones, who in his film debut is so good and convincing to the point that his character, Big Chris, is now considered an icon among crime/gangster film fans, especially in the UK. Last but not least, this entry is a shout-out to our editorial's most dedicated fan: our Big Chris from the comment section. Thanks for all the support, mate! 

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