Center for Creative Media | Top 10 Gangster Films

Top 10 Gangster Films

Top 10 Gangster Films

The trailer for a film I’ve been following for about a year was recently released. Black Mass, starring Johnny Depp as one of the most brutal and notorious gangsters in U.S. history — leader of the Irish American mob in Boston, Whitey Bulger. I love gangster films, especially about the Irish mob. I’d like to commemorate the release of this amazing trailer by sharing my list of top 10 gangster films. Some are classics from the 1930’s. And some are more modern and gritty, showing the reality of the violent and immoral life of the gangster. All are great examples of filmmaking and of the genre, although some are not family friendly.

1. Road to Perdition (2002)

This film is not only number one on my gangster movie list but number one on my movie list in general. Basically, this is my favorite movie of all time. Everything about it is beautiful. Director Sam Mendes assembles a star-spangled cast of Tom Hanks, Paul Newman, Daniel Craig, and Jude Law to bring the graphic novel to life.

The film follows the basic plot of the graphic novel as it casts light on the dark life of Michael Sullivan (Tom Hanks), a hit man for John Rooney (Paul Newman), leader of the New York sect of the Irish Mob. When Sullivan’s family gets mixed up in his work he’s forced to go on the lamb with his son, pursued by a sadistic killer (Jude Law).

Cinematographer Conrad Hall used the work of famous artist Edward Hooper as inspiration to bring the early 1930’s to life, creating perfectly iconic scenes filled with absolute beauty. His artistic genius in this film won him his third, and sadly last Oscar as he passed away only a few months after the release of Road to Perdition.

2. Angels with Dirty Faces (1936)

Angels with Dirty Faces still holds a special place for me. Not only is it the first gangster film I ever saw, but it awakened and solidified my admiration for actor James Cagney. Having no trouble living up to his tough guy persona, Cagney portrays gangster Rocky Sullivan, who has evolved from petty crime to make a name for himself. He uses underhanded deals with crooked lawyer James Frazier (Humphrey Bogart) to solidify his place in the criminal underworld.

When he stumbles across a group of hoodlum youth (the Dead End Kids), he takes them under his wing and mentors them in the way of crime. His enterprise is interrupted however by his boyhood friend Father Jerry Connelly (Pat O’Brien) whose mission it is to reform the youth and make sure they don’t end up on the same road as his crooked friend.

Oscar winning director Michael Curtiz (Casablanca) puts passion into every frame of the film from the very beginning, to its famous last scene that got Cagney nominated for the Oscar that year. In fact, the film was nominated for two other awards that year including Best Director (Curtiz), and Best Screenplay (Rowland Brown).

It’s not just me that’s a fan of this film, by the way. Director Chris Columbus loves this gangster flick so much that he shot two short parodies of it: Angels with Filthy Souls and Angels with Even Filthier Souls. You may recognize them as the gangster films that Kevin McCallister uses to frighten off the burglars in Columbus’s family comedy classics: Home Alone and Home Alone 2: Lost in New York.

3. The Godfather Part I and II (1972/1974)


No gangster film list would be complete without The Godfather films. These icons of cinema starring Marlon Brando, Al Pacino, and Robert De Niro give an amazingly beautiful picture of the Italian Mafia spanning from the early 20’s to 50’s. Although both are directed by Francis Ford Coppola, there is so much dispute on which of these films is superior and in my mind they are linked as far as greatness goes.

The first film stars Marlon Brando as the title character, Don Vito Corleone, the Godfather of New York City. He has spent his life building respect and wealth through organized crime. Now, his health is deteriorating and it seems the empire he worked so hard to build will soon follow suit. His only hope is to transfer control of the family to his youngest son, Michael (Al Pacino) who wants nothing to do with the family “business.”

The second film, which is arguably better than the first, goes back to Sicily 1910, where we discover the early life and origins of the boy who would be become Don Vito Corleone. After the murder of his family, he travels to America at age 10. It is here that the young adult Vito Corleone (Robert De Niro) begins to build the foundations for a vast illegal empire. Told side-by-side is the continuing story of Michael as he bring the the empire into the late 1950s and begins to slide further and further away from the man he hoped to be and further into darkness.

With a combined total of nine Oscars and 11 nominations, The Godfather Part I and II are perfect examples not only of gangster films, but of filmmaking in general. Earning Brando, Pacino and De Niro everlasting fame, Francis Ford Coppola captures the rich heritage and truth of the Sicilian as only an Italian American can. It should be noted here that there is a third Godfather film that Coppola did not want to make. However, since I am not making a list of “Top 10 Films that Nearly Ruined Franchises,” I will only mention its existence.

4. Miller’s Crossing (1990)

This beautiful, poignant film is an often overlooked Coen brothers offering. Called the “undiscovered jewel of the Coen Crown,” Miller’s Crossing is a prohibition-era gangster film marked with all the beauty and complexity one expects from the Coen brothers.

In 1920’s New York, Leo (Albert Finney) runs the Irish mob. He has all the respect and no one dares mess with him. Not even the rival Italian Mafia. All is peaceful until Bernie Bernbaum (John Turturro), a Jewish bookie, tries to steal from the Italians to line his own pockets. Italian Mafioso Johnny Caspar (Jon Polito) comes to see Leo for permission to kill Bernie. Given the fact that Leo is engaged to Bernie’s sister Verna, he cannot allow the hit. Caspar promises war and it’s up to Leo’s advisor Tom Reagan (Gabriel Byrne) to make peace. Filled with bullets, blood and half-truths, Miller’s Crossing remains one of the most intense, high-paced gangster films of all time.

5. Public Enemies (2009)

Being from Indiana, I grew up hearing stories of notorious gangster John Dillinger and his many bank robberies in the mid 1930’s. As a matter of fact, my hometown of Bedford is just over an hour away from Mooresville, Indiana hometown of the famous gangster.

Director Michael Mann (The Last of the Mohicans) was faced with the difficult task of bringing life to the legend. Wearing some of Dillinger’s actual clothes, Johnny Depp empowers Dillinger with cool but deadly suavity, while Christian Bale steps into the shoes of Special Agent Melvin Purvis, the FBI agent assigned to hunt him. With academy award winning actress  Marion Cotillard (Inception, The Dark Knight Rises ) as Dillinger’s girl Billie Frechette, Public Enemies is a fast-paced thrill ride that lends a gritty modern feel to the world of the 1930’s bank robbers.

6. The Public Enemy (1931)

This is the film that put James Cagney on the map. In 1930’s Chicago, two friends Tom Powers (Cagney) and Matt Doyle (Edward Woods) rise up in underworld to become two of the most prominent bootleggers in the Irish sector.

Nominated for Best Original Story, The Public Enemy is considered to be one of the most realistic portrayals of 1930’s gang life, and no wonder. Not only did Cagney base his performance of real-life gangster Charles O’Banion, but every time a Thompson machine gun was used in the film, real bullets were fired by an expert with the gun on a raised platform specifically designed to miss Cagney and his co-star.

7. The Departed (2006)

When a director like Martin Scorsese assembles a cast of Leonardo DiCaprio, Matt Damon, Jack Nicholson, and Mark Wahlberg, you know you’re not going to see a mediocre film. Scorsese has an affinity for gangster films and this one is a masterpiece.

When Irish mobster Frank Costello (Nicholson) pushes the line too far, Boston police officer Billy Costigan (DiCaprio) is assigned to use his rough, South Boston upbringing to infiltrate Costello’s operation and provide a constant stream of information that will lead to Costello’s arrest. Meanwhile, a prodige’ of Costello, Colin Sullivan (Damon) worms his way into the Boston Police Department as a mole feeding a constant stream of information back to the Irish boss. Add to the catalyst Police Lt. Bingham (Wahlberg) who works to keep Billy’s cover intact while trying to stir up the mole.

Scorsese orchestrates a symphony of suspense and embroiling politics. With his all-star cast, Scorsese turns everything upside-down and rockets the film to win four Academy awards including Best Picture and a Best Achievement in Directing.

8. Goodfellas (1990)

Scorsese once against takes the helm of a gangster film in this incredibly brutal look into the world of the Italian Mafia in the early 70’s. Based on actual events, mafia runner turned state’s witness Henry Hill (Ray Liotta) gives an account of his entrance into the mob life at an early age and his life as a “Goodfella,” a trusted friend of the La Cosa Nostra. His testimony points the finger at Mafia boss Paul “Paulie” Cicero (Paul Sorvino), Irish “Goodfella” James Conway (Robert De Niro), and sadistic murderer-for-hire Tommy DeVito (Joe Pesci).

True to his form, Scorsese doesn’t shy away from reality. Bringing the brutal violence of the underworld to life, this film can be difficult to watch. Especially since the viewer remembers that a fast majority of the savage and cold-blooded events depicted in the film actually took place. The reality of the film earned Goodfellas five oscar nominations including Best Picture. Pesci’s simply insane performance won him Best Supporting Actor.

9. The Roaring Twenties (1939)

  Director Raoul Walsh brings James Cagney and Humphrey Bogart together for their second collaboration in the single saddest gangster film I have ever seen, The Roaring Twenties. When three friends Eddie Bartlett (Cagney), George Hally (Bogart), and Lloyd Hart (Jeffrey Lynn) meet in the French trenches of WWI. Determined to make better lives for themselves if they ever make it home, their dreams are shattered when the return home to discover the world has moved on in their absence and there are no jobs available.

Bartlett and Hart stick together and enter the lucrative bootleg business during Prohibition. They become extremely successful and wealthy in no time. When they move to take over a rival mob boss’ shipment, they meet up with the sociopath Hally who has also made it good in the bootlegging business.

When Hart wants to go straight and pursue law, Bartlett has no trouble. Until Bartlett’s girl falls for him. As Bartlett begins to spiral out of control, the sneering Hally takes control of the business leaving death and destruction in his wake. This film truly has an ending that you won’t see coming and Bogart’s performance as the psychopathic murderer is absolutely chilling.

10. Little Caesar (1931)

When you think of a stereotypical 1930’s gangster, whether you realize it or not, you’re imagining Edward G. Robinson in the 1931 gangster classic Little Caesar.

Robinson comes to life as tough-guy Rico Caesar who makes a living with his partner Joe Massara (Douglas Fairbanks Jr.) robbing gas stations for whatever he can gets. When he gets tired of the small-time he heads up the coast with Massara to join a big-time gang. When he shoots the new police commissioner, Rico becomes emboldened and takes control of the mob, making his name and his wealth with the aid of his gun.

Honorable Mentions:

White Heat (1949)

Starring: James Cagney

Directed by: Raoul Walsh

Gangs of New York (2002)

Starring: Leonardo DiCaprio, Daniel Day-Lewis

Directed by: Martin Scorsese

The Untouchables (1987)

Starring: Kevin Costner, Sean Connery, Robert De Niro, Andy Garcia, Charles Martin Smith

Directed by: Brian De Palma

Gangster Squad (2013)

Starring: Sean Penn, Ryan Gosling, Emma Stone, Giovanni Ribisi

Directed by: Ruben Fleischer

Tim Martin

Tim Martin is from central Kansas where he briefly attended film school before coming to CCM. He grew up watching mostly silent films, classical cinema, and researching film history, Tim has a unique perspective on film for someone only 21 years of age, one that lends itself well to his roles as a writer and producer. When he’s not working, Tim enjoys reading, taking walks in the wood, and watching horror films.

Bradyn Litster