For over a century, the allure of stories of criminals and those who chase them has attracted audiences worldwide. That’s how the crime genre has become one of the most popular and prolific in film history—and as for gangster films in particular, the popularity’s all there as well. As long as the characters are part of some kind of organized crime syndicate, it’s a gangster movie, and several of them are among the greatest films of all time.
Whether it’s an early silent classic like Underworld; a film from Hollywood’s Golden Age like The Big Heat; or a modern international masterpiece like City of God, there’s something irresistibly appealing about watching these wrongdoers and/or the heroes that bring them to justice rise and/or fall in power. All sorts of stories can—and have been—told within this genre, and it has resulted in some truly exceptional gems.
20
‘The Penalty’ (1920)
It was roughly around the 1930s that the gangster genre exploded in popularity in Hollywood, instantly becoming the mainstay that it still is today. There were plenty of great gangster movies before then, however, one of the best and most important being Wallace Worsley‘s The Penalty. In it, a deformed criminal mastermind plans to loot San Francisco and get revenge on the doctor who mistakenly amputated his legs.
It’s one of the most intense silent movies ever made, starring an amazing Lon Chaney at the top of his game. The movie, which was based on Gouverneur Morris‘s pulp novel, was every bit as pulpy itself, a quality shared by most early gangster flicks. Its thematic work can feel a little dated, but Chaney’s legendary performance alone makes this a must-see.
19
‘Carlito’s Way’ (1993)
Al Pacino is an icon of both the crime and gangster movie genres, and during the ’90s, he was on fire. Legendary director Brian De Palma, one of the most important voices of the New Hollywood film movement, was also on fire throughout the decade. The duo have only collaborated twice, and though some people may prefer the first film they made together, Scarface, it’s the underrated Carlito’s Way that time has been kindest to.
Both De Palma and Pacino are at their best in this wild, explosive masterpiece that doesn’t let up for a single second of its nearly 2-and-a-half-hour runtime. The lead performance is a perfect mix of the physical subtleties of early Pacino and the huge outbursts of ’90s Pacino, and De Palma’s dynamic direction makes the film’s final half hour one of the most tense of any gangster film of the ’90s.
18
‘Underworld’ (1927)
In Austrian-American filmmaker Josef von Sternberg‘s Underworld, a boisterous gangster kingpin rehabilitates a former laywer from his alcoholic haze, but complications arise when he falls for the crime lord’s girlfriend. Paramount Pictures thought that this pulpy noir would be an all-out failure, but much to their (and everyone’s) surprise, Underworld was a smash hit both critically and commercially.
Today, though Underworld doesn’t receive nearly as much love as it deserved, it can nevertheless be considered one of the best silent movies of all time. As a pre-Code crime picture, it can be unexpectedly dark and erotic, which makes it an absolutely spellbinding experience the likes of which you can’t find in Hollywood’s Golden-Age filmography.
17
‘The Roaring Twenties’ (1939)
Raoul Walsh‘s The Roaring Twenties was designed as an homage to the many gangster pictures of the early 1930s. In the end, it ended up becoming an even bigger and more iconic classic itself. Spanning several years, passing through the Prohibition era and the 1929 stock market crash, its story is one of the most enthralling of any film of its genre from the ’30s.
That’s what makes it one of the best must-watch crime masterpieces ever. It was the third and last film that James Cagney and Humphrey Bogart made together, and it was instantly hailed as a masterpiece of the genre. With an impressive score of 100% on Rotten Tomatoes, it has been praised as an ambitious, hard-boiled gem that redefined Warner’s tone and style for gangster pictures going into the ’40s.
16
‘White Heat’ (1949)
Another iconic crime film from Hollywood’s Classical period, White Heat has more than just one of the most legendary movie ending scenes of all time going for it. It’s not only one of the greatest gangster flicks ever made, but also one of the best noirs of its era, starring James Cagney at the very top of his game. It was the actor’s big comeback to Warner Bros. after he left in 1942 to form his own production company, which ended up failing.
What a comeback it was. Cagney’s amazing in White Heat, but it’s the marvelous script and Raoul Walsh’s explosive direction that really make this come together as a masterpiece. Gangster pictures from the era never dove as deep into the criminal’s psyche as this movie did, and that depth makes this one of the most thrilling cops-and-robbers films from the ’40s.
15
‘The Big Heat’ (1953)
The Austrian-born filmmaker Fritz Lang is easily one of the most groundbreaking and legendary movie directors of his generation. Fleeing Nazi persecution, he made the jump to Hollywood in 1936, and he was just as successful there—if not even more so—than in Germany. For 20 years, he made some of the best American pictures of the era, which includes the noir thriller The Big Heat.
For about half of its narrative, the movie develops as a traditional police procedural, until it starts boiling into a full-on revenge thriller. It’s one of the best black-and-white noir films ever, a grim and intense tale of violence and corruption that’s perhaps best left untouched by those who don’t like when gangster movies leave them feeling hopeless for humanity.
14
‘The Departed’ (2006)
Despite being considered by many the greatest working filmmaker, Martin Scorsese has only ever directed one movie that made its way to a Best Picture Academy Award: The Departed. It may not be Scorsese’s best film, but it sure is one of his best modern outings, and its Best Picture victory was more than entirely deserved.
With its exceptional ensemble cast, its gritty tone, and its absolutely engrossing script, this remake of the 2002 Hong Kong film Infernal Affairs is far and away one of Scorsese’s best masterpieces. It’s a thriller firing on all cylinders throughout every second of its 151-minute runtime, the kind that has you biting your nails at the edge of your seat without even realizing it because it’s just that good.
13
‘The Irishman’ (2019)
For 13 years, Scorsese took a break from the gangster genre that so many people instantly associate with his name. Then, in 2019—perhaps the best year for cinema of the 2010s—, he made a big comeback 3-and-a-half-hour long epic The Irishman. Along for the ride also came another three of the genre’s biggest icons: Robert De Niro, Al Pacino, and Joe Pesci.
It’s the work of a master in full control of his craft and with perfect knowledge of what makes his genre work. It’s one of the most perfect gangster movies of all time, a riveting epic that was stuck in development hell for several years. It’s a moving, entertaining, and occasionally quite sad film that earns every single second of its daunting runtime.
12
‘Once Upon a Time in America’ (1984)
Sergio Leone was a filmmaker perhaps best known as the father of Spaghetti Westerns, but he also did work outside of that genre—and some of it is absolutely exceptional. Case in point: Once Upon a Time in America, a crime epic that clocks in at nearly four hours and, though not without its share of dated elements, is still one of the greatest epic masterpieces of the last 75 years.
Part gangster drama, part period piece, part sprawling coming-of-age, this quasi-Shakespearean tale of love, lust, greed, betrayal, and violence is one of the most stunning achievements that the Seventh Art has ever allowed. Sure, it’s long, but the gorgeous cinematography, Ennio Morricone‘s timeless score, and the emotionally engrossing nature of the story all make it worth every minute.
11
‘Gangs of Wasseypur’ (2012)
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Another extremely long film, Anurag Kashyap‘s Gangs of Wasseypur is a 5-and-a-half-hour long crime epic that had to be split into two parts because no Indian theater would screen a movie that long. In the end of the day, though, it was all designed as a single film, and it’s one of the greatest crime movies of the 2010s, at that.
Encompassing generations of violence and brutality, Gangs of Wasseypur makes 319 minutes go by surprisingly fast. It’s one of the best gangster epics ever made, as well as one of the most internationally acclaimed Indian films of the 21st century. There’s action, raw emotion, unexpected doses of delightful humor, and moments of quirkiness that all fans of Bollywood cinema will surely be able to appreciate.
