The 20 greatest gangster movies of all time, ranked

Despite the gangster genre’s many uniquely American qualities, organized crime has proven to be great fodder for British film, too. That’s best exemplified by The Long Good Friday, John Mackenzie’s fiercely intelligent, intricately constructed tale of intersecting underworld interests and political concerns. At the center is Bob Hopkins as Harold Shand, a devious mobster striving to go legit. Just as he’s about to close a king-making deal with his American mob counterparts, Shand’s considerable efforts are undermined by a destabilizing chain of events in his criminal realm. As his schemes unravel, so too does Shand in a can’t-look-away depiction of crime’s inevitable undertow.

There have been many bids to satirize the mob film genre over the decades, but none more darkly comedic and twisted than Prizzi’s Honor, the final work from pioneering film noir architect John Huston. The film is a bloody Valentine between two Mafia enforcers at cross-purposes—Jack Nicholson and Kathleen Turner, both in lustiest form—who fall in love. Beyond being an early entry in the increasingly ubiquitous hitman genre, the film is elevated by its pre-Sopranos exploration of family dynamics within the mafioso bubble, appropriately epitomized by the director’s real-life daughter Anjelica Huston. She stars as a Mafia princess and Nicholson’s scorned ex (the actors’ real-life romance added further resonance), who’s as iron-willed and ruthless as her elderly father, the mob don.

With The Untouchables, a sort of companion piece to his earlier gangster work Scarface, Brian De Palma shifts the landscape to 1920s Chicago, and the focus to the federal lawmen tasked with curtailing the operations of organized crime. De Palma follows famed crime-stopper Elliot Ness (Kevin Costner) and his band of incorruptible G-Men as they take on the Windy City’s supreme crime boss, the infamous Al Capone—played with demented relish by a no-holds-barred Robert De Niro, spouting deliriously tough-guy dialogue penned by David Mamet. Sleeker and more polished than Scarface, but in its way just as baroque and unrestrained, here De Palma favors morality over vice—but still has fun with his cinematic bloodbaths.

Simultaneously viewing the gangster film through the lens of urban Black American youth and launching a distinct genre of its own, John Singleton’s semi-autobiographical film Boyz N The Hood follows a well-established template, detailing the inexorable gravitational pull of crime, violence, retribution, and its fallout in gang-centric neighborhoods. The film traces the story of Cuba Gooding, Jr.’s Tre, who is determined not to fall prey to the streets. Like Scorsese before him, Singleton fills every frame with verite-like detail that suffuses the film with an overpowering sense of reality.

Peter Yates’ neo-noir The Friends Of Eddie Coyle is anchored by one of Hollywood’s finest post-Golden Era performances from Robert Mitchum—one of the rare screen icons to successfully bridge the gap between classic and modern film. Mitchum brings his trademark detachment and rugged individualism to Coyle, a mid-level career criminal looking to get out from under his life of extralegal activities, only to discover there’s very little trust and loyalty to go around, on either side of the law. The role feels tailor-made for Mitchum, who brings an aging spin to his aloof, quietly pained and world-weary demeanor in a film where there’s little honor among thieves—or anyone else.

In Mean Streets, his earliest entry into gangster cinema, Martin Scorsese reveals the power of his approach to the push-pull life of crime, and soaks his film in overwhelmingly authentic, immersive detail. The filmmaker intimately knew the characters’ real-world equivalents and their Little Italy neighborhood, and he uses that knowledge to freshen and richly inform a classic crime-versus-faith dilemma. The naturalistic acting of Harvey Keitel and Robert De Niro—the latter perfectly inhabiting the first of many of Scorsese’s volatile, dangerously unpredictable menaces—fit seamlessly into the conflicted tapestry the director so vividly creates, setting the stage for even greater collaborations to come.

The versatile hand of director Michael Curtiz guides Angels With Dirty Faces, a hard-edged but sentimental entry into the genre built around the lifelong bond between a small-time hoodlum (the screen’s archetypal gangster, James Cagney) and his childhood friend-turned-Catholic priest (the screen’s preeminent clergyman, Pat O’Brien). The man of God tries to steer the thug away from corrupting a gang of street youths, played with moxie by the Dead End Kids. Humphrey Bogart, in his pre-leading man mode, also has a key role as a corrupt attorney once in cahoots but now at odds with Cagney, who ultimately delivers a bravura heel turn to hammer home the “crime don’t pay” ethos.

As if Al Pacino didn’t already reign over the modern gangster film canon as its ne plus ultra actor, he reaffirms his title in Donnie Brasco, with a role that’s worlds apart from Michael Corleone and Tony Montana. Pacino stars as Lefty Ruggiero, a world-weary but too-trusting mob foot soldier who unknowingly plants the seed of his own destruction by vouching for Brasco, an undercover lawman seeking to tear down the mob family from within. As the infiltrator stricken with empathy for the man he’s betraying and besieged by a crisis of conscience as he toes the line of criminal behavior himself, Johnny Depp makes the film a potent two-hander that dissects law, lawlessness and loyalty.

Having already mastered the mob drama with Goodfellas, Martin Scorsese adapted the Hong Kong thriller Infernal Affairs with The Departed, giving the gangster genre a welcome goose by fusing it to a police potboiler rife with deception, double-crosses and jaw-dropping plot twists. Though the filmmaker never skimps on his expected cinematic flourish, he wisely leaves much of the heavy lifting to the uniformly stellar cast, led by Leonardo DiCaprio, Matt Damon, Vera Farmiga, and Mark Wahlberg. But amid all that star power and perfected Beantown accents, the supernova is Jack Nicholson, adding freshly detestable yet mesmerizing spins on another of his embodiments of The Devil Himself—this one inspired by infamous real-life Boston mobster Whitey Bolger.

The Coen brothers bring their crime noir sensibilities to Miller’s Crossing, a retro-gangster gem that wears its love of the genre on its sleeve. The film is loaded with references, subtle and overt, to the visuals and dialogue of the books and movies that influenced the sibling filmmakers—the works of Dashiell Hammett being a prime wellspring. Beautifully lensed in the noir tradition with an offbeat perspective by Barry Sonnenfeld, the gang power play plotline is secondary to a cast of the Coens’ signature quirky characters, here in mob dress, with a murderer’s row ensemble doing some of their best screen work, including Gabriel Byrne, Marcia Gay Harden, John Turturro, and Albert Finney.

With Bugsy, Barry Levinson delivers a gangster drama packaged in the trappings of a lush period romance—one nearly as carnally charged as Warren Beatty’s previous entry, Bonnie and Clyde, but with less grit and more gloss. Sparks fly between Beatty’s Hollywood mob boss/Las Vegas visionary Bugsy Siegel and Annette Bening’s mob moll/failed starlet Virginia Hill. Siegel’s bone-deep vanity is eclipsed only by his capacity for unhinged violence, while Hill’s seductive allure is only exceeded by her cunning ambition. Even with some historical liberties, it’s note perfect, down to the glorious Ennio Morricone score.

Less concerned with the glamorous trappings of the organized crime world or its dynastic bent, White Heat follows gritty anti-hero Cody Jarrett (James Cagney) through a failed scheme, and into prison, where he’s marked for murder by a rival. A cunning but desperate escape ensues, followed by his scrambling bid to rise back to, as he puts it, “the top of the world.” Cagney is at his most ferociously psychopathic as a demented, mother-dependent hood. Simmering with tension, violence and betrayal at every turn, Raoul Walsh’s film delivers a unique portrayal of a mobster as a flailing, wounded animal on the run, lashing out in every direction.

Edward G. Robinson’s Rico Bandello arrives fully formed as an ambitious, calculating and bloodthirsty sociopath eager to do whatever it takes to reach the top of his hoodlum empire in Little Caesar. The flip side to the genre-establishing counterpart The Public Enemy, the film is a star-making turn for Robinson, who plays Rico as a character whose ruthless immorality is his central attraction. That makes it all the more shocking when the merest glimmer of human sentimentality—Rico’s inability to exterminate his oldest friend—surprises even him, tipping the dominoes that lead to Rico’s inevitable downfall.

Sergio Leone may have made his reputation on convention-flouting Italian Westerns, but his balletic approach to cinematic ultra-violence was also ideally suited to the gangster genre, as expressed in Once Upon A Time In America. While his sprawling epic had a dismal showing at the box office, its uncut European edit only gains in stature with the passage of time. The film’s multilayered plot is enhanced by Leone’s stunning visual artistry, even as it looks shockingly, unblinkingly at the brutality and sexual violence of its world. Once Upon A Time is elevated greatly by both Robert De Niro’s searing performance as Noodles and Ennio Morricone’s masterful score.

The first postmodern gangster film, Bonnie And Clyde leans heavily into sex and violence and the intersection where they meet in their star-crossed lovers’ pathologies. A gun isn’t just a gun when it comes to Warren Beatty’s Clyde and his frustrated passion for Faye Dunaway’s Bonnie. The film’s tone intentionally see-saws between near-slapstick and bloody brutality. And its criminal anti-heroes are portrayed as effortlessly cool, stylish, erotic, and all mixed up underneath. That mix was absolute catnip to the Baby Boomers who made the film a surprise monster hit, and it’s a big reason for Bonnie And Clyde’s enduring appeal to subsequent generations of iconoclasts and authority-defiers.

Along with Little Caesar, The Public Enemy is the pre-Code sui generis that originated and defined the gangster genre for generations to come. The film is built around James Cagney’s brutal yet charismatic Tom Powers, who transcends his hardscrabble street origins through the grab-it-all wealth and status-by-intimidation of organized crime. Even as he delves deeper into the dark side of society, Powers tries to remain faithful to his disapproving family. His self-centered ambition and familial devotion endeared him to audiences and made him an anti-hero icon overnight. But lest viewers get ideas about the fruitfulness of crime, Tom’s precipitous downfall—he dies as roughly as he lived—provide Grace-of-God moral guidance for a film that remains a powerful template for criminal rises and falls.

Scarface is the gangster drama at its most coked-up. Brian De Palma’s taste for grand guignol-style cinema blends ideally with the genre here, as he dives headlong into the bloody business of crime in a way mob films of yore could never do. His characters snort up monstrous piles of blow to keep the film thrumming at a sweaty fever pitch, and capable of exploding at any moment. As Tony Montana, Al Pacino’s gonzo performance, voracious in all of Tony’s appetites and ever on the verge of batshit craziness, matches De Palma’s intentionally provocative, over-the-top-is-not-far-enough tone note for note.

Goodfellas easily tops the list of Martin Scorsese’s most broadly beloved films, and were it not for The Godfathers it would also be the greatest mob movie of them all. The story of Ray Liotta’s Henry Hill begins at street level, in the filmmaker’s signature style, following a guy from the neighborhood who finds his calling among career criminals. He wallows in the seductive glamour of his new world, including the unrepentant violence epitomized by his psychopathic pal Tommy DeVito (Joe Pesci), before realizing that his “family’s” only real loyalty is to ruthless expedience in the protection of its profits. Henry’s paranoic fall is even more dizzying than his rise, as perfectly expressed by Scorsese’s virtuosic mastery of kinetic cinematic imagery, unyielding commitment to authenticity and brilliant pop-rock needle drops.

There are countless arguments to be made about which installment of the greatest gangster epic ever committed to film is the superior, but why split hairs? As truly phenomenal as each portion of Francis Ford Coppola and Mario Puzo’s revered Corleone family saga may be, The Godfather and The Godfather Part II gain in power from each other. Pulpy and Shakespearean, intimate and operatic, Michael Corleone’s devotional fall into the corruptive pull of his family’s criminal empire—via Al Pacino’s legend-making performance—is an all-too-human and, given its immigrant origins, particularly American tragedy. The tale is writ large with universal, generational appeal, yet it’s rendered personally with a sumptuous visual sense. Somehow, the story never loses sight of the violent, avaricious thrills that made the gangster genre so enduringly popular. And even the saga’s coda, the inferior but still formidable The Godfather Part Three, offers a potent capstone to the whole bloody mythos.