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Best Gangster Movies of All-Time

Updated on October 13, 2013

The Godfather trilogy

Any list of the best films begins with The Godfather movies. The Godfather is a crime novel written by Italian- American author Mario Puzo, originally published in 1969, that inspired three major motion pictures. One of the most unforgettable moments in film history is when Michael orders the killing of his own brother, Fredo.

Marlon Brando --- Don Vito Corleone
Al Pacino --------- Michael Corleone
James Caan ------ Sonny Corleone
Robert Duvall --- Tom Hagen
Diane Keaton --- Kay Adams
Talia Shire -------- Connie
John Cazale ------- Fredo
Robert DeNiro ---- Young Vito Corleone



The Godfather movie trailer

Goodfellas

Many film enthusiasts will argue that Goodfellas is even better than The Godfather movies. Starring Ray Liotta, Robert DeNiro and Joe Pesci, this 1990 film directed by Martin Scorsese is based on the real-life gangster life of Henry Hill and his friends as they work their way up through the ranks of the mob. After spending a lifetime dedicated to his crime family, Henry is forced to become the lowest form of person to the mob, "a rat", to save himself and his family from a lifetime of incarceration and possible death.

Fun Fact: The F-bomb is dropped 296 times during the film ! Nearly half of them are by Tommy DeVito, played by Joe Pesci,.

Henry Hill: "Anything I wanted was a phone call away. Free cars. The keys to a dozen hideout flats all over the city. I bet twenty, thirty grand over a weekend and then I'd either blow the winnings in a week or go to the sharks to pay back the bookies. Didn't matter. It didn't mean anything. When I was broke, I'd go out and rob some more. We ran everything. We paid off cops. We paid off lawyers. We paid off judges. Everybody had their hands out. Everything was for the taking. And now it's all over."

The Untouchables

The tale of how federal agent Eliot Ness (Kevin Costner) and his hand-picked team of officers set out to stop the corruption of mobster Al Capone (Robert DeNiro). Also starring Sean Connery and Andy Garcia, this film directed by Brian DePalma (of Scarface fame) tells about life in 1920's prohibition-era Chicago and the constant battle to keep the criminal element at bay.

Other popular films by director Brian De Palma:

The Black Dahlia
Carrie
The Bonfire of the Vanities
Casualites of War
Femme Fatale
Carlito's Way
Scarface
Mission: Impossible
Snake Eyes
Mission to Mars
The Fury

Perhaps the most popular actor of the genre, Robert DeNiro
Perhaps the most popular actor of the genre, Robert DeNiro | Source

Carlito's Way

The second of three Brian De Palma films to make the list, Carlito's Way stars Al Pacino as Carlito 'Charlie' Brigante, the former "King of Smack". Carlito is determined to stay away from drugs and violence, but his past always seems to bring him back to his old habits. The film also stars Sean Penn, Penelope Ann Miller, and John Leguizamo (as the despicable Benny Blanco). Penn is especially brilliant in his role as Brigante's corrupt attorney who gets himself into trouble with the mob while struggling with his cocaine habit. The film barely broke even at the box office, but it's one of those hidden treasures that is a big hit with fans across the globe

Source

Donnie Brasco

This 1997 film by director Mike Newell stars Johnny Depp as an undercover FBI agent who infiltrates the mafia but struggles to separate his pretend life from the family life that he left behind. Al Pacino does a great job as Lefty Ruggiero, the veteran who takes Donnie Brasco (aka Officer Joe Pistone) under his wing and vouches for him to the crime boss. Donnie begins to feel compassion for Lefty and doesn't want to exit his assignment for fear that his new friend will be executed for his error in judgement.

An actual FBI surveillance  photo of Joseph D. Pistone , Benjamin "Lefty" Ruggiero and Edgar Robb.
An actual FBI surveillance photo of Joseph D. Pistone , Benjamin "Lefty" Ruggiero and Edgar Robb. | Source

Scarface

The 1983 classic film Scarface is yet another movie that was brought to us by director Brian De Palma. Starring Al Pacino as Tony Montana, it's a tale of two Cuban refugees who come to America for a better life away from the rule of Fidel Castro. Along the way, Tony and his friend Manny (Steven Bauer) do small-time jobs until they manage to meet drug kingpin Frank Lopez (Robert Loggia), which causes Tony to decide that he wants it all, including the kingpin's girlfriend, played by Michelle Pfeiffer. His rise to power comes with a price as he finds out that you can't stay on top forever with everyone else wanting what you have.

What drove these men to a life of crime ?

Vito Corleone (The Godfather) - Struggling to make ends meet for his family, Vito and his friends decide that there is more money in crime than in grinding it out with jobs. Plus, jobs were scarce back then for everyone, especially immigrants.

Henry Hill (Goodfellas) - Henry grew up fascinated by the gangster lifestyle, watching the local criminals spending time at the cab stand instead of out working their butts off for a few bucks.

Carlito Brigante (Carlito's Way) - Growing up on the streets of New York City, a Puerto Rican had little chance of finding a decent job. Instead, they were used as drug runners. Carlito managed to work his way up the ladder and become the "King of Smack" and was idolized by the younger generation.

Tony Montana (Scarface) - After joining a group of refugees coming to America from Cuba, Tony had very few options other than a life of crime. Originally content to work small-time jobs for small money, greed got the best of him when he saw how easy it was to start his own criminal enterprise.

Casino

From the creators of Goodfellas comes another great film from director Martin Scorsese and writer Nicholas Pileggi. Sam Rothstein, astute sports handicapper and known associate of the mafia, is sent to Las Vegas to run the Tangiers Casino. Along the way, he battles pressure from the locals regarding his policies and has a tumultuous relationship with hustler Ginger. Plus, his longtime friend Nicky is causing problems by drawing too much attention to Rothstein's attempts at keeping a low profile. If you haven't seen this film by now, you should make it a priority.

CAST

Robert DeNiro - Sam "Ace" Rothstein

Sharon Stone - Ginger McKenna

Joe Pesci - Nicky Santoro

James Woods - Lester Diamond

Kevin Pollak - Phillip Green

Don RIckles - Billy Sherbert

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Miller's Crossing

This very underrated look into the 1930's Prohibition-era tells the story of two gangs that are battling for control of the city. Tom Reagan gets into a disagreement with his boss over a bookie and winds up in the middle of a feud between both gangs. Loyalties are tested as Tom must decide if he really cares about anyone other than himself. Starring Gabriel Byrne, John Turturro, Steve Buscemi, and Albert Finney, this 1990 film was unnoticed by critics and audiences but is yet another well-written film by the Coen brothers.

This critically-acclaimed film from Martin Scorsese takes place in Boston, where mob boss Frank Costello runs his organization thanks in part to a mole he places in the Massachusetts State Police force. At the same time, the police send an undercover officer to infiltrate the Costello gang. It soon becomes a battle of wits as each of the double agents tries to figure out the identity of the other. The stellar cast includes such notables as Jack Nicholson, Leonardo DiCaprio, Matt Damon, Mark Wahlberg, Martin Sheen, Alec Baldwin, Vera Farmiga, and Ray Winstone.

Once Upon a Time in America

This 1984 Italian crime drama starring James Woods and Robert DeNiro chronicles the lives of youths who rise from lowly ghetto teens to prominence in the world of organized crime. Directed by Sergio Leone, who is well-known for his spaghetti westerns, this film is a lesson in broken hearts and the high price of choosing your own personal gain over your friends.

Robert De Niro as David 'Noodles' Aaronson
James Woods as Maximilian 'Max' Bercovicz
Elizabeth McGovern as Deborah Gelly
Joe Pesci as Joe
Tuesday Weld as Carol
Treat Williams as Police Chief Vincent Aiello

Sergio Leone's most popular films as director:

1984 Once Upon a Time in the West

1966 The Good, the Bad and the Ugly

1965 For a Few Dollars More

1964 A Fistful of Dollars

Final Words

The crime genre will always be of interest to movie audiences across the world, although some Italians and Italian-Americans feel a little slighted by the references and stereotypes. Whether you are a fan of Pacino, DeNiro, Pesci, or any of the other popular actors and directors of true crime flicks, there is something here for you to hang on your wall.

I hope to see you at the movies !

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    • Carl8033 profile image

      Alexander Okelo 4 years ago

      Wow, this really brings back old memories, especially the untouchables, I just loved that series.

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