Crime doesn’t pay? Try telling that to filmmakers. The gangster movie is among cinema’s most enduring genres, offering audiences the vicarious thrill of being bad. Its Golden Age came in the 1930s, when hard-edged, Pre-Code pictures such as Little Caesar, The Public Enemy and Scarface: The Shame of a Nation introduced a rogue’s gallery of Prohibition-created antiheroes.
In the decades since, the gangster saga has proved versatile enough to encompass everything from Japan’s Yakuza films (Battles without Honor and Humanity, The Yakuza) to 1976’s Bugsy Malone, an all-kid musical-comedy where pint-sized mobsters guzzle speakeasy sarsaparilla and fire tommyguns that spray whipped cream. At their best, gangster flicks are not simply crime stories but examinations of ambition, power, and greed.
Here are 10 of the best you can’t refuse.
10. Once Upon a Time in America (1984, dir. Sergio Leone)
For his last film, Sergio Leone turned his mythmaking deconstruction from the American Western to the gangster flick. Spanning 1922 through 1968, it follows Robert De Niro and James Woods as two Jewish kids from New York’s Lower East Side who grow up from petty hoods to crime kingpins. Once Upon a Time in America is epic in scope and elegiac in tone (thanks largely to Ennio Morricone’s haunting score), rich in period detail and boasting a strong ensemble cast—but it is also, oddly, emotionally distant. There are bizarre shifts in tone and, as evident in a brutal rape involving De Niro’s “Noodles” Aaronson, it is sometimes difficult to tell when a character’s misogyny ends and Leone’s begins. Some cinephiles contend the story is all an opium-induced hallucination of Noodles’. I’m not sure I buy that. The picture was doomed to have some problems with flow. The distributor chopped 90 minutes from the American version after Leone’s final cut clocked in just shy of four hours (its most comprehensive restoration came in 2012). However flawed, this saga remains fascinating, ambitious, and eminently watchable.
9. White Heat (1949, dir. Raoul Walsh)
Gangster movies are rife with bad guys who have a soft spot for mother, but White Heat’s Cody Jarrett is in a class by himself. As portrayed by James Cagney, Cody is to mama’s boys what Picasso was to cubism. He loves Ma Jarrett (Margaret Wycherly) with near-Oedipal fervor. She’s the brains of his criminal gang, sure, but Cody treats Ma like royalty while he barks orders at his hot-but-trashy wife (Virginia Mayo) as if she were an indentured servant. White Heat is a whirling dervish of a film. Raoul Walsh, who Cagney had previously worked with on The Roaring Twenties (see #8) keeps the pace brisk and the vibe brutal, but most of the energy derives from the star; billed as his comeback, Cagney is fury incarnate. The man contorts his face into a fist. While the movie’s climax is rightly ingrained in pop culture (“Top o’ the world, Ma!”), few moments can rival the scene when Cody is in a prison mess-hall when he learns of his mother’s death. He erupts in guttural howls that reportedly shocked the room crowded with extras posing as inmates.
(See more in The 15 best film noir and 10 memorable movie mothers.)
8. The Roaring Twenties (1939, dir. Raoul Walsh)
When the studio system was thrumming along in the 1930s and ‘40s like the efficient machine it was, Hollywood cranked out fast-paced stories that did what they needed to do and got out before you started to check the time. Raoul Walsh’s The Roaring Twenties exemplifies that craftsmanship. Based on a story by producer Mark Hellinger, it follows three American GIs who meet in a foxhole during the First World War—Eddie (James Cagney), George (Humphrey Bogart) and Lloyd (Jeffrey Lynn)—and cross paths later during Prohibition when Eddie is a top bootlegger. Cagney’s Eddie Bartlett is several shades more interesting than Warner Bros.’ run-of-the-mill movie gangster. He’s tough, certainly, but also a lovesick sap when it comes to Priscilla Lane as a lounge singer he finances to be a star but loses to do-gooder Lloyd. Cagney’s commanding screen presence (see #9’s White Heat) sometimes obscured what a skilled actor he was. The Roaring Twenties is a reminder that he could also dig into a character’s vulnerability.
7. Scarface (1983, dir. Brian De Palma)
“Say hello to my little friend!” This blood-soaked remake of Howard Hawks’ 1932 crime picture graduated from movie to meme many decades ago, but Scarface is a pop-culture touchstone for a reason. This is pulp fiction writ large from director Brian De Palma, screenwriter Oliver Stone and lead Al Pacino—creatives not exactly known for timidity. Tensions ran high on set, especially between De Palma and Stone. Pacino, toting an M16 fitted with a grenade launcher, is deliriously over-the-top as Tony Montana, a Cuban refugee who arrives via the 1980 Mariel boatlift and becomes Miami’s drug kingpin. Supporting players Michelle Pfeiffer and Stephen Bauer try to get some attention when Pacino isn’t snorting up all the oxygen, and cocaine, on screen. De Palma being De Palma, there are suspense sequences so meticulously crafted as to be fitting for a museum exhibit, and there is enough debauchery and excess to trigger the DTs afterward. A critical and commercial disappointment upon release, its stature has only grown in the ensuing decades. No less a fan than Saddam Hussein slapped the name Montana Enterprises on a corporation he had set up for money-laundering.
6. The Long Good Friday (1980, dir. John Mackenzie)
An alternate title for The Long Good Friday, the last great British crime thriller of the 1970s—although eventually released in 1981, it was completed in 1979, so I’m counting it—could be Bob Hoskins and the Terrible, Horrible, No Good, Very Bad Day. Hoskins is a barely contained drum of nuclear rage as East London crime lord Harold Shand. A vicious hoodlum hoping to reinvent himself as a respected businessman, he is in the midst of trying to ink a real-estate deal with the American Mafia on a particularly difficult Good Friday (duh). The timing isn’t ideal. For reasons eventually explained, the Irish Republican Army has picked this day to blow up or otherwise murder Harold’s closest associates, including a car bombing outside a church where Harold’s mother is attending services. “You don’t go crucifying people outside a church on a Good Friday!” says the exasperated mob boss. Director John Mackenzie and screenwriter Barrie Keeffe go for a methodical slow burn as Harold, his girlfriend Victoria (Helen Mirren) and his minions struggle to save their criminal empire. The picture made Hoskins a star, and rightly so. His wordless final close-up is a masterclass in acting.
5. Carlito’s Way (1993, dir. Brian De Palma)
Leaving the gangster life isn’t easy. Just ask Al Pacino, who had already traveled that road in The Godfather saga (“Just when I thought I was out, they pull me back in!” he snaps in The Godfather III). In Carlito’s Way, he is Carlito Brigante, a muckety-muck in New York’s Puerto Rican mob newly released from prison. He wants to go straight but discovers that is easier said than done. Carlito is barely out of the joint before he finds himself in a pool-hall shootout defending his cousin Guajiro from other hoods. Brian De Palma’s post-Scarface (see #7) reunion with Pacino is a solid genre entertainment anchored by David Koepp’s muscular script and a centerpiece scene at Grand Central Station that ranks among De Palma’s best work. Sean Penn has more fun as Carlito’s coke-snorting slimeball defense attorney, David Kleinfeld. Pacino is less volcanic here than in Scarface—we have a rooting interest in Carlito—but his accent is no more convincing than his Cuban accent as Tony Montana.
4. City of God (2002, dir. Fernando Meirelles and Kátia Lund)
Warring gangs, the ever-looming threat of violence, and even roving bands of gun-wielding prepubescents—as portrayed in City of God, all characterize thug life in the favela, a shantytown on the outskirts of Rio de Janeiro. An international sensation upon release, the Portuguese-language adaptation of Paulo Lins’ 1997 novel spans more than 20 years in the infamous ghetto. Rocket (Alexandre Rodrigues), who has aspirations to escape, dreams of becoming a professional photographer. Benny (Phellipe Haagensen) is an affable drug kingpin who would rather party than kill. On the other end of the spectrum, his friend Li’l Zé (Leandro Firmino) is a crime boss with unquenchable bloodlust; he isn’t even a teenager before he is responsible for mass murder. The visceral propulsion created by directors Fernando Meirelles and Kátia Lund is reminiscent of Martin Scorsese, but City of God is its own singular beast, its rawness and energy driven by fast edits, split screens, vibrant colors, docudrama techniques and a quicksilver soundtrack of funk and samba. The picture inspired a Brazilian television series and was instrumental in revitalizing world cinema from that country.
3. The Godfather (1972, dir. Francis Ford Coppola)
A box-office smash, cultural phenomenon and winner of three Academy Awards, The Godfather redefined the gangster movie. Paramount Pictures took a considerable chance entrusting the adaptation of Mario Puzo’s bestseller to Francis Ford Coppola. Nothing in the resume of the 32-year-old director indicated he was ready for a project that had the studio’s fortunes riding on it. Coppola’s vision was crucial to the film transcending its genre. In Mark Seal’s Leave the Gun, Take the Cannoli: The Epic Story of the Making of The Godfather, Coppola said he realized there was “the core of a profound story, one of a classic succession concerning a great king with three sons, each of whom had a single element of what made the king great.” Casting auditions seemingly included every actor with a SAG card; the studio wanted Ryan O’Neal or Robert Redford to play Michael Corleone. And once production was underway, a New York Mafia family boss named Joe Colombo founded a sketchy Italian-American civil rights organization that successfully pressured Paramount to quash any overt reference in the picture to the Mafia or Cosa Nostra. Marlon Brando won (and subsequently refused) the Best Actor Oscar for the role of Vito Corleone, but every bit his equal are Al Pacino and James Caan as sons Michael and Sonny, with John Cazale quietly devastating as the weak-willed middle son, Fredo. If there’s a weakness in the movie, I haven’t found it after countless viewings over the years. From Gordon Willis’ innovatively low-light, high-contrast camerawork (inexplicably snubbed by the Academy Awards) and Nino Rota’s haunting music score to a pitch-perfect cast, The Godfather deserves its reputation as not only one of the greatest gangster stories, but one of cinema’s best-ever films.
(See more in The 10 best bathroom scenes in film and 10 memorable movie fathers.)
2. Goodfellas (1990, dir. Martin Scorsese)
Martin Scorsese had long kicked a cocaine habit by the time he made Goodfellas. It’s worth noting because otherwise one might think this hyper-kinetic rollercoaster is the product of a coke binge. Like the devil’s powder, Goodfellas is enthralling, seductive and potentially addictive, as it is eminently rewatchable. Unlike cocaine, repeated exposure isn’t bad for you. Based on Nicholas Pileggi’s nonfiction Wiseguy, chronicling the life of mob informant Henry Hill, the picture envelops itself in the extravagant gangster lifestyle like no other movie had done. As a child growing up in Brooklyn, Henry is enamored of the bigshot hoodlums in his neighborhood flashing wads of cash. He winds up working for one, Paul Cicero (Paul Sorvino), and becomes fast friends with fellow mobsters Jimmy Conway (Robert De Niro) and Tommy DeVito (Joe Pesci). “The movie took gangsters off the wobbly pedestal popular culture erected in honor of The Godfather movies and made them into something like ‘regular’ guys again,” Glenn Kenny writes in Made Men: The Story of Goodfellas. The cast is extraordinary across the board, though Pesci’s portrayal as the unhinged Tommy steals every scene and earned him a Best Supporting Actor Oscar. Scorsese’s movie is big and bombastic, the work of a master filmmaker at the height of his powers. Its episodic structure allows for several bravura set pieces. Henry and his future wife Karen (Lorraine Bracco) visit the legendary Copacabana in an impressive, unbroken traveling shot immersing us in the excitement of the moment. A lengthy montage of the day that led to Henry’s arrest is a dazzler punctuated by rock ‘n’ roll needle-drops and Thelma Schoonmaker’s breakneck editing. In illustrating both the evil of organized crime and its undeniable appeal, Goodfellas is the most daring—and perhaps honest—of morality tales.
1. The Godfather Part II (1974, dir. Francis Ford Coppola)
This ranking does not weigh in on the ongoing debate among cinephiles over which Godfather picture is better. Both I and II are masterpieces (and III, for that matter, is better than its reputation despite Sofia Coppola’s performance). But as a full-throated gangster saga reflecting the 1950s and early ‘60s, The Godfather Part II is superb. The screenplay by Francis Ford Coppola and Mario Puzo examines the pivotal roles of Las Vegas and pre-Castro Cuba in cementing the Mafia’s dominance in American organized crime while also exploring the impact of congressional investigations (led in real life by Tennessee Sen. Estes Kefauver) into mob leaders. Lee Strasberg is particularly terrific as Hyman Roth, a thinly veiled version of Meyer Lansky, among the architects of modern-day organized crime. But Part II is equal parts sequel and prequel. Robert De Niro portrays Vito Corleone as a young immigrant in the Little Italy of early 20th century New York, a part for which the actor learned to speak Sicilian. A key cast change is the addition of Michael V. Gazzo as Corleone family capo Frankie “Five Angels” Pentangeli. Essentially, the character replaces Part I’s Clemenza, who disappeared from the script after actor Richard Castellano demanded a bigger salary and that his wife write all his dialogue. Coppola wasn’t messing around for the sequel. Unlike the first film, Paramount ceded him complete control this time. Building on its predecessor, The Godfather Part II lays bare the corrupting of American institutions, from business to government and beyond. Although it cleaned up at the Academy Awards with six wins, including Picture, Director, Adapted Screenplay and Best Supporting Actor (De Niro), not all critics were smitten. The New York Times’ Vincent Canby groused that the most notable thing about Coppola’s movie was that “it recalls how much better his original film was.” C’est la vie—I’m not sure what the Sicilian translation is.
Honorable mention: Animal Kingdom (2010, dir. David Michôd), Battles without Honor and Humanity (1973, dir. Kinji Fukasaku), A Better Tomorrow (1986, dir. John Woo), The Departed (2006, dir. Martin Scorsese), Donnie Brasco (1997, dir. Mike Newell), Eastern Promises (2007, dir. David Cronenberg), The Friends of Eddie Coyle (1973, dir. Peter Yates), King of New York (1990, dir. Abel Ferrara), Miller’s Crossing (1990, dir. Joel Coen), Scarface: The Shame of a Nation (1932, dir. Howard Hawks)
Cutting to the Chase with Phil Bacharach 