Gangster movies have been a staple of cinema since the silent era, with Fritz Lang's Dr. Mabuse, the Gambler laying early groundwork for the genre. By the time talkies arrived, classics like Scarface (1932), Little Caesar, and The Public Enemy defined the archetype. Yet it took until the second half of the 20th century for a gangster film to win the Academy's top prize. In fact, no crime movie claimed Best Picture until 1954—and even that one is a borderline case.
For this ranking, we're defining "gangster movie" broadly: any film centered on organized crime or featuring characters who are mobsters or deeply entangled with the underworld. That excludes West Side Story (teen gangs) and crime thrillers like The Silence of the Lambs or No Country for Old Men. Over nearly a century of Oscars, only five movies that fit the bill have won Best Picture. Here they are, ranked from worst to best.
5. The Sting (1973)
Sandwiched between two of the most legendary gangster films ever made, The Sting often gets overshadowed—but it deserves its own spotlight. Paul Newman and Robert Redford play con artists, not full-fledged mobsters, but their target is a powerful crime boss who murdered their friend. Their elaborate revenge scheme is part heist, part comedy, and wholly charming.
Some might argue it's not a gangster movie at all, and they'd have a point. But the organized-crime element is strong enough to qualify. The film's laid-back tone and infectious chemistry between its leads make it a breezy caper, even if you'll hear "The Entertainer" about 500 times. It's a fun, stylish romp that holds up, even if it's the weakest of the five.
4. The Departed (2006)
Martin Scorsese had already made Mean Streets, Goodfellas, and Casino before The Departed finally earned him his long-overdue Best Picture win. Compared to those earlier masterpieces, this one feels more like a taut thriller than a traditional gangster saga—but that's not a knock.
The plot is a cat-and-mouse game: an undercover cop infiltrates a Boston mob, while a mole from the gang infiltrates the police. The suspense is relentless, and the cast—Leonardo DiCaprio, Matt Damon, Jack Nicholson—delivers powerhouse performances. If it's not Scorsese's best gangster film, it's still a gripping, expertly crafted crime drama that earns its place among the winners.
3. On the Waterfront (1954)
Like The Sting, On the Waterfront is a gangster movie by association rather than identity. Marlon Brando plays Terry Malloy, a former boxer caught between corrupt union bosses and the longshoremen they exploit. The gangsters here are the ones running the docks, and Terry's moral awakening drives the story.
Brando's Oscar-winning performance is iconic, and the film's themes of conscience and corruption resonate deeply. It's a phenomenal movie—though 1954 also gave us Seven Samurai, which might be even better. Still, On the Waterfront is a powerful, character-driven drama that set a new standard for the genre.
2. The Godfather Part II (1974)
The only sequel to win Best Picture, The Godfather Part II is a staggering achievement. It weaves two timelines: young Vito Corleone's rise in early 1900s New York, and Michael Corleone's descent into ruthless power in the 1950s. Robert De Niro and Al Pacino both deliver career-defining performances.
This is a gangster epic that expands the world of the first film while deepening its themes of family, betrayal, and the American Dream. It's darker, more complex, and arguably more ambitious than its predecessor. For many, it's the pinnacle of the genre—but it still has to bow to the original.
1. The Godfather (1972)
There's no contest. The Godfather is not just the greatest gangster movie to win Best Picture—it's one of the greatest films ever made. Francis Ford Coppola's adaptation of Mario Puzo's novel is a masterclass in storytelling, character, and atmosphere. Marlon Brando's Don Vito Corleone is an icon, and Al Pacino's transformation from reluctant son to cold-blooded don is mesmerizing.
The film's influence is immeasurable, from its cinematography to its dialogue ("I'm gonna make him an offer he can't refuse"). It's a tragedy, a family saga, and a meditation on power and corruption. Every frame is perfect. If you've never seen it, do yourself a favor—and if you have, watch it again. It only gets better.
For more on the best of cinema, check out our ranking of the most universally beloved thriller movies of all time or explore the sci-fi movies that defined the genre.
