The Greatest Gangster Movies

Gangsters have always made for great subjects for movies. Sure in real life they may be immoral criminals, but thanks to Hollywood there is a romanticized version of them we know from pop culture. From the Warner flicks of the Depression to contemporary crime epics, people love good movies about bad people.


The Godfather: Many have claimed this to be the greatest American film of all time, and it is hard to fault them because the Godfather is a flawless picture. Reigniting the career of Hollywood legend Marlon Brando, Francis Ford Coppola’s masterpiece about the Corleone family stands the test of time. The Corleone family’s black sheep, Michael has returned home from serving in the military and tries to establish an identity outside of his family’s criminal enterprises. But when the enemies of his family start gunning for his father Don Vito Corleone, Michael is reluctantly pulled into the family business. We in the audience can only watch with rapt attention as this young man with the best of intentions slowly but surely loses his soul.

Al Pacino In 'The Godfather: Part II' Woody Allen And Mia Farrow In 'A Midsummer Night's Sex Comedy' '

The Godfather Part II: One of the few sequels which is just as good as (or possibly better than) the original. Michael now controls the family, but instead of making things easier he now finds himself besieged on all sides by those looking to take him out. The reluctant patriarch must deal with rival gangsters, the US government, and even his own brother while holding onto power. In the Godfather Part II, we see that the price Michael must pay for his decisions, and Al Pacino sells this perfectly with his haunted brooding performance. His struggles in the present are juxtaposed with a story in the past of his own father’s rise to power. Now played by Robert DeNiro, a young Vito immigrates to America to build his own American Dream and avenge his father’s death at the hands of Don Ciccio.


White Heat: At the height of his career James Cagney took a break from playing gangsters and take on roles where he could play more kindhearted characters, who often sang and danced. But in 1949 he returned to the genre which made him a household name. In White Heat, Cagney plays the most evil and ruthless gangster he has ever played in Cody Jarrett. Directed by Raoul Walsh in a noir-esque style, Cagney dominates every scene he is in as a crazed mobster who inspires fear in those around him. When his mother, the only person in his life he cares about is murdered, Cody’s mind completely snaps. This leads to him escaping prison to reestablish his position in the criminal underworld and killing anyone in his way. Dealing firsthand with the criminal’s mental instability is his trusted second in command, who is secretly an undercover cop. It all leads to an explosive finale which stands as one of the greatest moments in film history.


Scarface: Sure this movie is a remake of a 1932 Howard Hawks movie with Paul Muni and George Raft; but it is the 1983 version that has engrained itself into our memories. As the cocaine dealing Tony Montana, Al Pacino gives audiences one of the most iconic film characters of all time, even recognizable to those who have never seen Scarface. Directed by Brian DePalma, Scarface follows Montana as he rises from a Cuban refugee to a full fledged crime boss trying to make the world is. The movie does a brilliant job showing the darker side of the “American Dream”. His desires to gain power and wealth drives the character in both his rise to power and brutal death in one of the most iconic climaxes in movie history.


Carlito’s Way: Years later Al Pacino would reunite with his Scarface director, Brian DePalma for another classic gangster tale. After five years in prison Carlito has been released and hoping to start a new chapter in his life.  Unfortunately his lawyer, played to protection by Sean Penn, wants to drag him back into his old life. As Carlito begins to fall back into the life he is trying to escape the feds and rival gangsters are waiting for him to slip up so they can take him out.


Once Upon a Time in America: True director, Sergio Leone is forever associated with the Western genre, he proved he could make a memorable crime movie as well. This crime epic follows a group of Jewish-American immigrants over the course of the several years. Chronicling their rise from the streets and the fall of these characters is nothing short of compelling. Along the way we see them deal with events like Prohibition and the Labor movement. Upon the initial release American audiences were short-changed with a more than an hour edited out which deprived them of the entire story as seen in European cinemas.


Casino: Once again Robert DeNiro proves to be the perfect choice if you need an effortlessly cool tough gangster. Reuniting with his Goodfellas collaborators Joe Pesci and Martin Scorsese, DeNiro plays Ace Rothstein, a gangster who moves to Vegas to make his fortunes in the underworld there. Over the decades we see he and his friend Nicky running the Tangiers casino through the 70’s and 80’s and era when the mob ruled Las Vegas.


The Roaring Twenties: Made in 1939, this is often hailed as the final epic of the Warner Bros. series of gangster films. Bringing together both James Cagney and Humphrey Bogart, two luminaries of the genre for a third and final flick together. Beginning during the First World War, Eddie, George, and Lloyd seem bound by fate throughout the decade of the 1920’s. George takes a chunk of the alcohol business and enlists his friends to aid him. Eddie is a mechanic who provides the cars for bootlegging purposes and Lloyd uses his law practice to take care of problems on the legal front. Things are running great at first but soon mistrust causes their criminal enterprise to crumble. They all turn on each other and in the end they all end up dead despite the fact they used to be “big shots”.  


Little Caesar: A good crime boss in a movie is one you automatically know he’s in charge as soon as he walks onto the scene. That is why Edward G. Robinson is one of the greatest actors to ever play a gangster. Robinson became synonymous with gangsters with his iconic look and voice. Easily the most influential flick in his filmography is Little Caesar, which paved the way for so many other mob flicks which followed.  His character Rico moves to Chicago with his best friend Joe in order to fulfill their dreams in the big city. Life in the Windy City leads them to the world of organized crime, and while Joe leaves it behind to find life as a dancer, Rico only wants to gain influence in the mob. Sure enough he takes over the criminal underworld of Chicago but as expected things begin to crumble. This drives Rico to the old flophouse he came from years ago for one final stand.


High Sierra: After being broken out of prison, Humphrey Bogart’s character, Roy ‘Mad Dog” Earle is blackmailed into returning to a life of crime. An aging mob boss, Big Mac,  is looking to make one final heist and Earle is just the one to help him. A team is put together to pull off the job but things go south. Roy now finds himself on the run with a girl he met at a dance hall named Marie. Together they must evade the police and try to make it to the Sierra mountains. High Sierra perfectly plays up the gangster movie archetype of the career criminal being reluctantly pulled back in for one last job.


Goodfellas: When the criminal career of real life mobster Henry Hill was brought to the silver screen, it benefited from the talent of Martin Scorsese. Every since Hill was a poor kid in New York he aspired to be a gangster, eventually joining with Jimmy Conway and the psychotic Tommy DeVito (played by Joe Pesci in an Oscar winning role). He does not see the dark side of this lifestyle but rather the romanticized version of life as a gangster. Inevitably this family he is a part of  crumbles into distrust and betrayals. Eventually the law catches up to Henry Hill and he is forced to help take down those closest to him. Despite being 25 years old, Goodfellas still holds up as one of the greatest crime epics of all time.  This is to the credit Scorsese taking inspiration of the classic mob movies and modernizing them into something contemporary in telling this story.


The Public Enemy: The movie that made James Cagney a star. Originally playing the role of sidekick, Cagney’s intensity and distinct talking style got him bumped up to playing the lead as Tom Powers. Tom is a major player in the bootlegging business who has no problem with using violence to keep his status. This is very much to the dismay of his brother, a veteran of the First World War who constantly stands up to Tom. The Public Enemy will forever be remembered for the famous scene of Cagney smashing a grapefruit into Mae Clarke’s face. This classic is often lauded for taking a much more realistic look at the gangster lifestyle than most of the other movies of the era.


Black Caesar: A blaxpoitation classic starring genre icon Fred Williamson as Tommy Gibbs a young man who rises from tough street kid to kingpin of Harlem. Writer and director Larry Cohen sought to tell the classic story of a criminal’s ascension to power and inevitable fall, but in a hipper and more contemporary setting. Suffering an from police officers on a kid, convinces Gibbs he is under the rule of “the man” and he has to turn to a life of crime in the hopes of turning the tables. He eventually rises through the ranks of criminality as he battles and defeats the white crime family to solidify his power. Adding to the coolness of Black Caesar is a soundtrack courtesy of the great James Brown. Almost immediately after this flick became a hit a sequel was released in the form of Hell up in Harlem.


The Petrified Forest: In a roadside diner at the edge of Arizona’s Petrified Forest; a gangster, an aspiring writer and a waitress all cross paths. Humphrey Bogart plays Duke Mantee, a grizzled mobster who has taken the patrons in the diner hostage while the police turn up the heat looking for him. Leslie Howard and Bette Davis are trapped as the tension rises and Mantee grows more desperate. While trapped with each other the characters all move in different and unexpected ways as Petrified Forest eventually makes its way to an unforgettable ending.


Angels with Dirty Faces: A group of kids are caught in a battle of morality between James Cagney’s Rocky and Pat O’Briens’s Father Connolly. It is the battle of wits between the two characters which makes this film so captivating. Filling out the cast around Cagney and O’Brien are fellow film greats, Humphrey Bogart and George Bancroft. No doubt the memorable ending to Angels with Dirty Faces is a major reason it is so beloved. As Cagney must face the consequences for his criminal actions, he concedes to O’Brien’s spiritual character and acts cowardly to embarrass himself and his lifestyle in front of the kids he was trying to tempt away.