10 Greatest Movie Gangsters of All Time, Ranked by Their Popularity

10. Bill Cutting from Gangs of New York (2002)

Authoritarian, ruthless, and cunning, Daniel Day Lewis’ Bill the Butcher stole the screen in Gangs of New York every time he appeared. His presence alone was menacing enough to make people drop on their knees and pray, and his impeccable skills with the knife only added a flair of danger to the man that already embodied it.

9. Nucky Thompson from Boardwalk Empire ( 2010–2014)

Nucky’s silver tongue and immaculate looks made him into the most charming type of gangster: the one everyone loves. Thanks to his persuasive skills and the ability to seamlessly blend his legal and illegal businesses, Steve Buscemi’s Nucky controlled the entirety of Atlantic City with few who could — or wanted to — oppose him.

8. Frank Costello from The Departed (2006)

Jack Nicholson managed to make his Frank Costello a proper charmer. This Irish crime lord preferred to largely stay behind the scenes, pulling strings and increasing his influence while evading law enforcement. His mysterious flair and suave and manipulative manners made his every scene captivating and intriguing.

7. Sonny LoSpecchio from A Bronx Tale (1993)

Chazz Palminteri’s extravagant approach to portraying the Italian-American gangster Sonny LoSpecchio resulted in a colorful and memorable character. Sonny’s eccentric manners and love for bright clothes made him stand out in every crowd and threw off his enemies, allowing the mobster to put his shrewd mind to use and get rid of them.

6. Nicky Santoro from Casino (1995)

Apart from his iconic portrayal of Tommy DeVito in Goodfellas, Joe Pesci killed it as Nicky Santoro in Casino. This mobster’s explosive personality and violent methods made him the guy few people would try to mess with, but despite his animalistic nature, his unwavering loyalty to his people made him borderline sympathetic.

5. Jules Winnfield from Pulp Fiction (1994)

Samuel L. Jackson ensured everyone who watched Pulp Fiction would remember Jules Winnfield. This assassin gangster is composed and charismatic, prone to intense monologues and love to quarter pounders, and spends most of his on-screen time trying to avoid killing people — but when someone jumps him, he’s a menace.

4. Jimmy Conway from Goodfellas (1990)

Without a doubt, Robert De Niro is the man to call when you need a spectacular mobster in your movie, and he proved it once again with Goodfellas. Jimmy Conway combines the two most important qualities of a true crime lord: the charm of a true gentleman (hence his nickname, The Gent) and the cunning of a chess player.

3. Tony Soprano from The Sopranos ( 1999–2007)

We rarely see on-screen gangster as something more than their archetypes, but Tony Soprano is an entirely different story. Brilliantly portrayed by James Gandolfini, Tony shows that even the hardest criminals are still people, and we learn a lot about this charismatic and ruthless mafia boss’s life from his counseling sessions.

2. Tony Montana from Scarface (1983)

No one knows more about achieving the American Dream than Tony Montana, and no one knows about the American Dream going wrong than those who saw Al Pacino’s iconic movie Scarface. Tony Montana rose from the bottom to the very top, becoming a larger-than-life drug kingpin with admirable ambition and power hunger.

1. Vito Corleone from The Godfather (1972)

The most famous fictional gangster of all time, Vito Corleone is primarily known as the Godfather. In the iconic movie trilogy, he was played by Marlon Brando. Vito’s calm demeanor, unwavering loyalty to his family, and unrivaled wisdom allowed him to become one of the most powerful people in the underground world whose powers extended far beyond the “official” boundaries of his criminal empire.