The best gangster movies of all time reveal a treasure trove of memorable characters, unforgettable plot lines and violent set-pieces that are all grounded in reality.
Although the golden age of La Rosa Nostra is decidedly in the rearview mirror – operating much more stealthily than past figures like John Gotti who is the latest to get a film adaptation – Hollywood continues to churn out the rags-to-riches stories.
We’ve sifted through the centuries of Hollywood work to unearth the 20 best gangster movies of all time. Rather than ruffle too many feathers, we’ve presented them alphabetically – as all 20 should be on your watch queue.
A Bronx Tale
A Bronx Tale blends traditional gangster film tropes with a a rock-solid coming-of-age backbone which speaks not only to the growing pains of getting older, but also issues relating to love, race, duty and heroic influences.
For as wonderful of a film as Martin Scorsese’s Goodfellas was, A Bronx Tale is a shining example of how the film could have possibly played out if the director had decided to focus the entire film on Henry Hill’s youth.
Although the pairing of director Brian De Palma and Al Pacino will probably be best remembered for their work on Scarface, there’s no denying that their reunion a decade later is a certifiable classic.
In Carlito’s Way, De Palma opts to tell the story of Carlito Brigante non-sequentially – showcasing his demise before we ever see the tireless work he puts into crafting his empire.
What makes this plot device so satisfying is that the best mafia movies don’t rely on smoke and mirrors. Rather, it’s the inevitability and sense of dread that comes along with living a certain lifestyle. As the audience, we get to feel that sense of unease for the film’s entire running time.
While Las Vegas seemingly has more in common with Disneyland than the Copacabana these days, Casino is Martin Scorsese’s reminder that the desert oasis was built upon the interests of connected men throughout the United States.
Telling the story of Sam “Ace” Rothstein – a reinterpretation of real life numbers man, Lefty Rosenthal – we see the push and pull between someone attempting to go straight, and those around him that want to utilize the shimmering palaces as facades for murder and mayhem.
Based on the 2002 Hong Kong thriller, Infernal Affairs, the aforementioned, Martin Scorsese, traded the Eastern influences for a Boston-based locale where the line between cop and crook was as murky as the waters in the harbor.
The cat and mouse game between Leonardo DiCaprio and Matt Damon is particularly thrilling to watch unfold. It also speaks to an overarching theme we see in many of the best gangster films; impressionable little boys grow up and become what they see. But in a not so simple word, their duality is what makes The Departed feel so new and unexpected.
Donnie Brasco tells the true story of Agent Joseph Pistone who infiltrated the Bonanno crime family in the 1970s using the movie’s title as his codename.
Effortlessly portrayed by Johnny Depp, the film really soars when a relationship blooms between he and Al Pacino’s character, Lefty, who both seemed to understand that no matter what side of the law you’re on, it’s all just a rat race.
The French Connection
Based on the extraordinaire lives of New York City detectives, Eddie Egan and Sonny Grosso – who thwarted a global heroin ring in the early 1960s – The French Connection is the perfect balance of grittiness and entertainment.
With Gene Hackman installed in the role of Popeye Doyle – which won him an Oscar for Best Actor in 1972 – the character is decidedly immoral and not the typical hero that Hollywood was churning out at the time. Thusly, we get a scene where Hackman’s character tortures a black man dressed as Santa Claus.
What’s particularly nice about this film is that it doesn’t glamorize New York City. Rather, it reveals all the pockmarks and scars which gives the narrative a truly believable quality.
Francis Ford Coppola’s masterwork remains as vital to the genre as any film prior or post its 1972 release date.
Although the director was only 30 at the time, he was wise enough to see that Mario Puzo’s source material was ripe with interpersonal and complicated family relationships which were vital in elevating the subject matter from pulpy to genius.
In his production diary for the film, Coppola even noted the pitfalls he would face in telling the story of the Corleone family; writing, “cliches, Italians who-a, talka lika dis, failure to make a convincing setting. People must feel that they are seeing a real thing.”
To achieve this, Coppola put the audiences in the shoes of Michael Corleone. As a character, he was far removed from the typical Italian goombah that the director wanted to avoid. Even after his father’s injuries – and subsequent actions – Michael remained a living, breathing person as opposed to an ideal.
The Godfather II
It’s the movie debate that continues to be a hot button issue; is the second installment of The Godfather trilogy better than the original film which scored three Oscars for Best Picture, Best Actor and Best Adapted Screenplay?
From a pure awards standpoint, The Godfather II outpaced the original film – nabbing awards in the aforementioned categories and additional wins for Best Director, Best Original Music and Best Production Design. It also holds the distinction of Robert De Niro becoming the first actor to win for performing in a language other than English.
In both films, Vito Corleone is of vital importance. Whereas in the original, we get Marlon Brando’s portrayal of the patriarch, De Niro’s embodiment of the character brings a vitality to the role and allows us a greater understanding into the mind of a man who would have no problem sticking a horse head in a man’s bed, but also wanted so desperately to keep his youngest son out of the life.
As to the case of what’s better? That’s like choosing between the perfect sunrise and the most idyllic sunset? It’s a matter of mood.
The dual narrative is a hallmark of many Martin Scorsese films. However, it’s particularly effective in Goodfellas because not only does it provide context as it relates to mafia elements, but Karen’s narrative arc and explanation adds a whole new level of depth to the genre. For one of the first times, we understand the intoxicative effects of a life of crime with a strong female point of view.
Many films are cemented as classics for their ability to keep your attention even if you’re starved for time and only have a few minutes to catch one scene while it runs on cable TV. With Goodfellas, the entire film plays like that. Whether it’s the infamous tracking shot, “funny how?” exchange, Billy Bats, and the shoe shine, Goodfellas itself is like a string of standalone shorts that have been artfully cobbled together.
It would be hard to leave Infernal Affairs off this list given the narrative similarities between it and the the U.S. remake, The Departed.
Trading the Irish underbelly in Boston for the triads in Hong Kong, the same inherent tension is present as we watch the drama unfold between Chan Wing-Yan and Lau Kin Ming who are on opposites sides of the law and have varying allegiances.
For those who haven’t seen it, there are substantial differences between the two films – both in the visual style of the filmmaking and editing – and plot-wise. One could even argue that the ending in Infernal Affairs is much more realistic and plays up the guilt of living life as a perceived knight in shining armor, but with the heart of a rat.
One of the most effective underlying subplots in any of the best mafia movies is the direct competition between one’s real family/friends and the mafia brotherhood.
In Mean Streets, Harvey Keitel’s character, Charlie, is torn between his ambition to rise up the ranks, and his brother-like bond with Robert De Niro’s, Johnny Boy, who is like bacon grease lathered on each rung of a ladder.
In film, we tend to latch onto the people and events that have grandiose qualities. Brian De Palma’s Scarface comes to mind. Mean Streets is the antithesis. It’s a mafia movie about those who get stepped on.
There’s no mistaking a Coen brothers movie. Regardless of the genre, they have a strong point-of-view and a way of peeling back the layers to strike the perfect tonal balance between humor and drama by utilizing relatable character traits like greed, jealously and ambition.
Built upon a cast of unreliable characters as trustworthy as a house of cards set against a hurricane, we’re treated to watching Gabriel Byrne attempt to play multiple sides of a feud between Irish and Italian gangsters.
Once Upon a Time in America
While Sergio Leone will perhaps be best remembered for his work in the Western genre – having been the architect of screen gems like A Fistful of Dollars, For a Few Dollars More, The Good, The Bad, and the Ugly and Once Upon a Time in the West, he trained his sensibilities on the mob genre in 1984.
For most, this was surprising since the auteur had actually turned down The Godfather when it was offered to him. However, when he became enthralled with the life of Herschel Goldberg, he knew he had to explore the depths of the character.
The result is a film rife with drama thanks to a memorable performance by Robert De Niro as Noodles – who was forced to reconcile with the guilt that had plagued him for most of his life – and illustrated prominently through the use of dreams, hallucinations and flashbacks.
Quentin Tarantino has demonstrated a unique ability to bounce from genre to genre. Although he has put a finite number on the films he has left in his arsenal, he has declared his love for the gangster genre and hasn’t ruled out a return, stating, “A couple of things left that would be fun is I like the idea of doing a ‘30s gangster movie, so like Dillinger or Bonnie and Clyde kind of stuff. That’d be kind of cool.”
In his storied filmography, Pulp Fiction will probably be what Tarantino is best remembered for. Told non-linearly – with poetic hitman, brutalized gang bosses and prideful boxers – each narrative jolt is a shock to the system.
When speaking with AFI, Tarantino broke down all the aspects he felt went into making a successful gangster film, noting, “you need an aspect of criminality that you want to put under a microscope. In almost all cases, gangster films are sort of parodies of the American dream. They’re the looking glass; the bizarro world of getting rich in business in America.”
In the case of Reservoir Dogs, he focused on the immediate aftermath of a heist gone wrong. Slowly, we begin to unravel how a get-rich-quick scheme will have deadly consequences for everyone involved.
There’s a reason why Brian De Palma’s Scarface deserves a place at the table. Besides it being wickedly entertaining – tracking Al Pacino’s manic portrayal of Tony Montana – but there’s actually something relatable to the overall pursuit.
For as much talk there is today about the differences that define us, we can all agree that everyone is in a pursuit for something greater. Generationally speaking, parents want their kids to have it better than they did, and so on, and so on.
While the majority of us will never experience a meteoric rise like Tony Montana, we all can appreciate that feeling of stripping off an apron at a dead-end job and moving on to the next thing.
As is the case with many other Quentin Tarantino-written films, True Romance doesn’t tidily fit into a single genre. However, the scene between Christopher Walken and Dennis Hopper solidifies it as a gangster classic and laid the foundation for long, drawn out soliloquies we’d find in future works like Reservoir Dogs and Inglorious Basterds.
In the audio commentary about the scene in question, Tarantino called it “one of the proudest moments of my entire career.”
Featuring a murderer’s row of talent – including Brian De Palma, David Mamet, Robert De Niro, Kevin Costner, Sean Connery and Ennio Morricone – The Untouchables dips its feet into true events which chronicled the vice grip hold that Al Capone had on the city of Chicago and the subsequent response from Bureau of Prohibition agent, Eliot Ness.
Whereas even the most casual mob movie fan is aware of Al Capone’s exploits, they may be surprised to learn that one of the most brutal scenes in the entire film – where Capone unsuspectingly lures turncoat associates to dinner and beats them all to death with a baseball bat – was rooted in truth.
The violence depicted was relatively bold for audiences in the late 1980s. Specifically, there’s a shot that depicts brain matter being splattered against a white, marble wall. At the time, this sense of authenticity was quite jarring for moviegoers who only associated a gunshot wound with the faux-grabbing of one’s torso.
The Usual Suspects
For 95 percent of The Usual Suspects, the film feels like a heist film with unsuspected consequences for the band of men involved. The underlying mafia elements – recalling the infamous Keyser Söze – who hired the thieves, seems like simple window-dressing to explain certain expositional motivations.
However, that remaining 5 percent of the film reveals one of the most shocking and unexpected turns in cinematic history and solidifies not only Söze as a mastermind, but also a gangster with unmatched cerebral qualities.
Although this compilation is decidedly slanted to more modern fare, it would be a travesty to leave out Raoul Walsh’s 1949 classic, White Heat.
Starring James Cagney in the role of a lifetime as Cody Jarrett, a complex criminal who thinks and reacts with humanistic qualities despite the propensity of characters back then to feel quite Vaudevillian, the film explores the depths of criminal behavior and the impact on those on the periphery.