Top 10 Fictional Movie Gangsters | Articles on WatchMojo.com (2024)

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Welcome to WatchMojo, and today we’re counting down our picks for the most ruthless gangsters featured in movies. Just so we’re clear, they have to be fictional, so don’t go looking for Henry Hill from “GoodFellas,” or any of his fellow real-life wise guys. Also, beware of spoilers! Is there a movie gangster you’re “whacking” your foreheads that we forgot? Bark all day at us in the comments, little doggies! Just don’t bite!

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“Sexy Beast” (2000)

Sir Ben Kingsley is probably not the first actor one might think of as a gangster, but as Don Logan, he’s unforgettable. Don approaches his old friend Gal who’s retired in Spain for “one last job.” However, even though Gal desires to enjoy his retirement, Don insists. Profane and completely self-absorbed, Don Logan is one of the most overbearing movie characters in cinema. His inability to let go of what he wants is profoundly childish, yet his intense, menacing pursuit of his goals is also terrifying. Bottomline - Don is the embodiment of the phrase, “with friends like these, who needs enemies?”

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“Road to Perdition” (2002)

Tom Hanks makes for another unlikely gangster, but he hits this role out of the park, just like his other performances. Playing Michael Sullivan Sr., a mob enforcer for a Chicago gang, Hanks’ character is raised like a son by the gang’s leader, John Rooney. However, things turn sour when Rooney’s biological son, Connor, orchestrates the murder of nearly all of Sullivan’s family. Forced to go on the run with his own son, Michael Sullivan Jr., the protagonist seeks revenge for his family’s deaths, while also struggling to secure a better life for his son. Hanks delivers a fantastic portrayal of Sullivan – one of brutal violence mixed with fatherly instinct. Good or bad, he’s still a dad.

“Reservoir Dogs” (1992)

Each member of the gang this film focuses on is memorable in their own ways, but some personalities are bigger than others. In every crew, there is a loose cannon, and in this one, it’s Mr. Blonde. Real name Vic Vega, or “Toothpick Vic,” Mr. Blonde is the man responsible for his gang’s diamond heist turning into a bloodbath. A smooth-talking psychopath, Mr. Blonde can be charming, with his dry humor and amusing turns of phrase. However, his infamous torture of a cop the crew has captured, while dancing to “Stuck in the Middle with You,” illustrates that beneath that exterior lies a profoundly disturbed individual.

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“City of God” (2002)

Easily the youngest entry on our list, Li’l Zé is the young kingpin of the City of God, a neighborhood of Rio de Janeiro. A violent sociopath, Li’l Zé, known as Li’l Dice as a child, has risen to the top of his local underworld by being willing and eager to kill. His glee for murder makes nearly every scene he’s in full of tension, since anyone could die if he decides to indulge in his favorite pastime. The loss of his best friend Benny removes what little restraint Zé previously had, prompting him to engage in a lengthy gang war. Ultimately, as is the case with many gangsters, the many enemies Zé makes eventually catch up with him.

#6: Keyser Söze

“The Usual Suspects” (1995)

Some serious spoilers ahead on this one. Even criminals have a boogeyman. Before John Wick, the name that made them reconsider their life choices was Keyser Söze. After disabled criminal Verbal Kint is caught, he recounts how he and several of his fellow gangsters were enlisted by the shadowy crime boss Keyser Söze for a job gone awry. Söze never shows his face, and few who work for him even know it’s him they’re working for. By the film’s end, it’s clear that Kint’s story is partially fabricated, with details drawn from his surroundings. Not only that, Kint is Keyser Söze! Machiavellian and half-myth, Keyser Söze is a master criminal and a legendary gangster. And like that…

#5: Frank Costello

“The Departed” (2006)

A Boston mob boss of Irish descent, Frank Costello rules his city’s criminal underworld with brutality and brains. He has informants within the police force and personally tips off the FBI about his rivals, allowing him to remain one step ahead of both his competition and the cops. When Billy Costigan joins his organization, Frank suspects him of being a rat, but also comes to see himself in the young man. Throughout the film, Frank’s demeanor veers from being violent one minute to laugh-out-loud hilarious the next. And given that it’s Jack Nicholson playing him, he just oozes charisma every time he’s on screen! He may appear careless, but this is one meticulous and crafty gangster.

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#4: Jules Winnfield

“Pulp Fiction” (1994)

Quentin Tarantino movies are loaded with colorful criminals and ne’er-do-wells. While big boss Marsellus Wallace is more of the mobster archetype, his enforcer/hitman Jules Winnfield is one bad mother! Effortlessly cool in basically everything he does, Jules is among the most quotable gangsters out there. The apartment scene alone is downright legendary! Many of his expressions and jokes have become the sources for countless memes. However, a near-death experience causes Jules to reexamine his line of work. He may quote the Bible often, but it’s only after witnessing this miraculous event that Jules is inspired to be the “shepherd,” rather than “the tyranny of evil men.” We’d be down to watch him “walk the Earth” forever!

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“The Godfather” franchise (1972-90)

A quintessential embodiment of the rise and fall of a gangster, Michael Corleone is someone you do not want to mess with. Initially, Michael wants nothing to do with the “family business” of organized crime. However, the murder of his first wife and the needs of the family force him to step up and take charge, becoming the new godfather. However, as he navigates the leadership of his crime syndicate, he gradually loses his way, alienating or executing members of his real family. Michael Corleone could easily take the top spot - he’s one of the most iconic gangster characters ever and Al Pacino’s performance is unforgettable. Even so, there are some fictional gangsters who are equally, or even more, legendary.

“Scarface” (1983)

Look, Al Pacino has played a lot of great gangster characters, among them is Carlito Brigante from “Carlito’s Way,” which was even made by the same director as “Scarface.” Yet few of Pacino’s roles, or indeed few other gangsters in any medium are as electrifying as Tony Montana. A Cuban immigrant, Tony works his way up through the criminal underworld from its lowest gunman to become a drug kingpin of Miami. Pacino’s captivating, unhinged performance is endlessly watchable. He brings to life a character whose journey is a twisted tale of the American dream, a rags to riches story of blood and drugs. If there’s a poster child for the excess and danger of the gangster life, it’s Tony. [“Say hello to my little friend!”]

Before we unveil our top pick, here are a few honorable mentions.

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He’s a Smooth Customer Who Always Looks Out For Himself

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A Cash Money Gangster Who Knows How to Make Change

Vincenzo Coccotti, “True Romance” (1993)

A One Scene Wonder, But Oh-So-Memorable!

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#1: Vito Corleone

“The Godfather” franchise (1972-90)

The face of mobsters everywhere, Vito Corleone is the original Godfather. Vito comes to America after fleeing Italy, following the death of his parents at the hands of a local gangster. In the States, he works his way up to become a respected figure in New York, eventually assuming the role of the Godfather. His old school gangster ways prioritize the welfare of his neighborhood and friends, rather than violence meant for profit. Whether he’s played by Marlon Brando or Robert DeNiro, Don Vito is the OG to end all original gangsters. And for anyone who thinks otherwise, well, Don Vito has a proposal…