10 Great Portrayals of Gangsters on Film

Hollywood has a long tradition of depicting real life and fictional gangsters on film, and that tradition continues with the new movie 'Black Mass,' which features Oscar nominee Johnny Depp as notorious Boston gangster Whitey Bulger. With the new film opening in theaters on September 18, we have compiled a list of the 10 greatest portrayals of gangsters on film. 

Marlon Brando's performance as Don Vito Corleone has become the gold standard of gangster portrayals. It’s hard to believe now that the studio didn't want the legendary actor and actually made him screen-test for the role. It hardly mattered as Brando went on to create the most iconic mobster in movie history and win an Academy Award for his performance.

Al Pacino is another actor that Paramount originally did not want in 'The Godfather.' But director Francis Ford Coppola fought for Pacino and eventually the young actor was awarded the role. While Pacino's performance was somewhat overshadowed by Brando in the first film, he really got a chance to shine in the sequel. His best moment came when he kissed his brother full on the mouth, knowing that he would have him killed, and said the unforgettable line, "I know it was you Fredo. You broke my heart!"

Daniel Day-Lewis is widely considered our greatest living actor, so when legendary director Martin Scorsese decided to tell the story of the birth of the Irish mob in mid-19th century New York, he brilliantly cast Day-Lewis as Bill "the Butcher" Cutting. The result was an authentic and often disturbing portrayal of one of our country’s first gangsters. As Bill would say, "Whoopsy daisy!"

Liotta rose to fame with his portrayal of real-life mobster-turned-snitch Henry Hill in 'Goodfellas.' Liotta's ability to go from hysterical laughter in the "How am I funny?" scene, to menacing fear when he beats up Karen's neighbors, makes his gangster performance one of the best in cinema history.

While Joe Pesci won an Academy Award for his performance in 'Goodfellas,' it’s his lesser known turn as mobster Nicholas "Nicky" Santoro in 'Casino' that makes our list. One of Pesci's best scenes is when Ace (Robert De Niro) innocently asks the gentlemen next to him at the bar if he has dropped his pen. When the patron responds to Ace rudely, Nicky suddenly, violently and repeatedly stabs the man in the neck with the pen, just because he disrespected his friend.

Robert De Niro brilliantly played the small but pivotal role of legendary gangster Al Capone in the ensemble film 'The Untouchables.' While he only appears in a few scenes, De Niro was able to convey both the sense of fear that Capone levied over Prohibition Chicago, as well as the unusual celebrity that the mobster cultivated. For evidence of this, look no further than the explosive baseball bat scene or Capone’s furious "I want him dead" and "you got nothing" speeches.

1991’s 'New Jack City' was a groundbreaking gangster movie because it was one of the first films in the genre to feature an inner-city drug lord as its antagonist, instead of a mafia godfather. Wesley Snipes played the dangerous and narcissistic Nino Brown, whose Cash Money Brothers gang ruled the streets of New York dealing crack cocaine in the late '80s.

Ironically, Jack Nicholson’s role as Francis "Frank" Costello in 'The Departed' was loosely based on Whitey Bulger, the character Johnny Depp is playing in 'Black Mass.' One of Nicholson's most violent scenes takes place in the bar when Costello breaks Billy Costigan's (Leonardo DiCaprio) arm, for a second time, just to make sure he is not wearing a wire.

In this Ridley Scott masterpiece from 2007, Academy Award-winner Denzel Washington plays real-life Harlem gangster Frank Lucas, who smuggled heroin into the United States inside the coffins of dead Vietnam soldiers in the 1970s. Early in the film, Washington demonstrates why Lucas is the king of the streets when he abruptly interrupts his breakfast to shoot a crooked employee (Idris Elba) dead in broad daylight, only to calmly resume his meal afterwards with no remorse.

Academy Award-winner Christopher Walken gave one of the best performances of his career as mafia boss Don Vincenzo Coccotti in 'True Romance.' His most memorable scene is when Coccotti is interrogating Clifford Worley (Dennis Hopper) for the whereabouts of his son. Knowing he will die soon anyways, Worley bombards Coccotti with racial slurs until the gangster murders him in cold blood and says, "I haven’t killed anybody since 1984."