Wiseguys and White Heat: the 15 Greatest Gangster Films of All Time

Wiseguys and White Heat: the 15 Greatest Gangster Films of All Time

“As far back as I can remember, I always wanted to be in a gangster movie.”

No, that’s not quite the line from Martin Scorsese’s Goodfellas, which turns twenty-five years old today, but rather it’s from our favourite homage to the 1990 classic — yes, we’re talking about the chicken finger episode of “Community.”

Though that particular episode of “Community”’s real focus is on Abed’s elaborate chicken finger pyramid scheme, it does single out Scorsese’s Goodfellas as one of the quintessential gangster films ever made — one that’s still so distinct in our collective memory that a fictional film major on a television show can say a single line of recycled dialogue, and you half-expect a Robert De Niro cameo.

In celebration of Goodfellas’ twenty-fifth anniversary, we compiled a list of the greatest gangster films of all time — from Hollywood to Hong Kong.


White Heat (Raoul Walsh, 1949)

In the 1940s and 50s, Hollywood got to work at adapting the hardboiled crime fiction of Dashiell Hammett and Raymond Chandler, importing stylistic tropes from German Expressionism, all while creating a new kind of American cinema — a heyday for gangsters on film — called the “film noir.” Adhering to the gorgeously dark house style of Warner Brothers, Raoul Walsh directed perennial tough guy James Cagney in the role of White Heat’s Cody Jarrett, a deranged gangster whose attachment to his equally ruthless mother (Margaret Wycherley) is far from normal. Cagney, who Stanley Kubrick and Orson Welles considered to be one of the best actors of all time, also starred in the 1931’s proto-noir The Public Enemy, which really should be on this list as well.


Bonnie and Clyde (Arthur Penn, 1967)

With more than enough machismo and testosterone to fill a few dozen Clint Eastwood movies, it’s no surprise that the gangster genre is populated mainly by men. For that reason, Bonnie and Clyde has a very special palace in our hearts, as it allows for a very different type of gangster: a female one. Faye Dunaway is Bonnie Parker, a Depression-era outlaw who — along with her partner in crime, Clyde Barrow (Warren Beatty) — starts off as an amateur thief, only to become a sought-after bank robber with a gang of her own. Bonnie and Clyde, one of New Hollywood's first, is also credited as a leader in a progressive, unrestrained representation of sex and violence on film.

The French Connection (William Friedkin, 1971)

Inspired by actual events, William Friedkin’s The French Connection follows Jimmy "Popeye" Doyle (Gene Hackman) and Buddy "Cloudy" Russo (Roy Scheider), two New York Police Department detectives who stumble upon a drug smuggling outfit with ties to France. The French Connection became the first R-rated movie to win an Academy Award for Best Picture, and also scored wins for Best Actor (Hackman), Best Director (Friedkin), Best Adapted Screenplay, and Best Editing.


The Godfather I & II (Francis Ford Coppola, 1972 & 1974)

Of course Francis Ford Coppola’s The Godfather films are listed here — well, the first two at least. Starring Marlon Brando, Al Pacino, Diane Keaton, Robert Duvall, and Robert De Niro, The Godfather films enjoyed both critical and box office success in the 70s, and are now widely regarded as some of the greatest films ever made, ranking behind only Citizen Kane on the American Film Institute list of cinema’s best. Coppola’s Corleone saga is so entrenched in our popular culture that Tom Hanks repeatedly references the “mattresses” and “cannoli” in a — wait for it —Meg Ryan rom-com (You’ve Got Mail). You know you've made it when..?


Mean Streets (Martin Scorsese, 1973)

With Goodfellas, Casino, The Departed, and the aptly named Gangs of New York ahead of him, Martin Scorsese was to become one of the leading directors in the gangster genre, but it all started here with Charlie (Harvey Keitel) and Johnny Boy (De Niro). Mean Streets only cost $500,000 to make — chump change in comparison to Gangs of New York’s $100 million — but the small film was championed by film critic Pauline Kael, allowing Scorsese to jumpstart his streak of not only working with Robert De Niro, but also making some of the best gangster movies ever made.


Scarface (Brian De Palma, 1983)

With the film poster voted “Most Likely to be Owned by Your College Boyfriend,” the bullet-infested Scarface was directed by the director of Carrie, Brian De Palma, and written by Natural Born KillersOliver Stone. With those two credits alone, it’s no wonder that Scarface is beyond bloody; De Palma even received criticism about the film’s excessive violence in depicting the rise of Cuban refugee-cum-drug kingpin Tony Montana (Al Pacino). The film's legions of fans aren't complaining, however.


Once Upon a Time in America (Sergio Leone, 1984)

Based on Harry Grey's novel The Hoods, Once Upon a Time in America is the third instalment of Sergio Leone’s “Once Upon a Time” trilogy, which also included The West and The Revolution. With music from the legendary Ennio Morricone — who also scored the other Prohibition era film on this list, The UntouchablesOnce Upon a Time in America stars De Niro and James Woods as two young men who escape the Jewish ghetto on the Lower East Side by becoming involved in organized crime.


The Untouchables (Brian De Palma, 1987)

Any gangster movie made after 1973 has an 86% chance that Robert De Niro is in it. De Niro has been in so any gangster movies that he actually has a scene in The Family where he waxes nostalgic about Martin Scorsese — as a gangster. It’s super weird. In The Untouchables, De Niro’s there of course, but the film’s focus isn’t on De Niro or his portrayal of Al Capone. Instead The Untouchables approaches the gangster film from the other side of the cellblock, as Kevin Costner and Sean Connery — in an Academy Award-winning role — are government agents determined to end Prohibition and bring Capone to justice. Boasting a script from David Mamet as well as music from Ennio Morricone and — wait for it — Duke Ellington, The Untouchables is a worthy addition to any best-of gangster list even though the focus is on the Feds.


Goodfellas (Martin Scorsese, 1990)

Starting with its iconic long tracking shot through the Copacabana nightclub, Goodfellas is Scorsese’s quintessential love letter to the gangster genre. In the film, Henry Hill (Ray Liotta) idolizes the Lucchese crime family, and he does an admirable job at convincing the audience of the same before all hell breaks loose. First person narration kind of does that to you. Co-starring De Niro and Lorraine Bracco, Goodfellas banked six Academy Award nominations with Joe Pesci winning the Best Supporting Oscar for his role as Tommy DeVito.


Miller’s Crossing (Coen Brothers, 1990)

You may recognize the above troubled face as that of The Usual Suspect’s Keaton. Before we suspected Gabriel Byrne to be Keyser Söze, however, the Irish actor starred alongside John Turturro and Albert Finney in the Coen brothers’ neo-noir, Miller’s Crossing. Like the noirs of the 1940s and 50s, Miller’s Crossing was influenced by Dashiell Hammett, and the Coen brothers sought out the Hammett novels “The Glass Key” and “Red Harvest” as inspiration for their Irish and Italian mobsters — even lifting dialogue from the novels for the film.


Boyz n the Hood (John Singleton, 1991)

Filmed in South Central LA, Boyz n the Hood is a different kind of gangster film, where slick-haired mobsters in three-piece suits are traded out for street racing Crips and Bloods in dated 90s streetwear. The John Singleton film starred Ice Cube in the height of his N.W.A fame, Cuba Gooding, Jr., and Laurence — or rather “Larry” — Fishburne, and was nominated for two Oscars, making Singleton (then 23!) the youngest director to be nominated by the Academy


Reservoir Dogs (Quentin Tarantino, 1992)

Though the film has since become a cult hit — even labeled the “Greatest Independent Film of All Time” by Empire — Quentin Tarantino’s Reservoir Dogs wouldn’t have seen the light of day without Harvey Keitel. Tarantino had been working as a video store clerk at the time when Keitel, one of the core actors in gangster cinema, decided to take a chance on the fast-talking director and co-produce the film, becoming Mr. White. The pair would re-team for Pulp Fiction two years later, eventually winning the Palme d’Or at Cannes.


Casino (Martin Scorsese, 1995)

Before Martin Scorsese found another muse in Leonardo DiCaprio, the Queens, N.Y. director kept up his run of gangster films his eighth collaboration with De Niro — Casino. Like Goodfellas, the script for Casino was an adaptation of a Nicholas Peliggi novel. In the film, Ace Rothstein becomes involved with the Italian mob in Vegas, and of course things don’t go terribly well. Joe Pesci, who also stars in the film, didn’t repeat his Goodfellas nomination with Casino, but Sharon Stone managed to grab a nom for her role as Ginger McKenna, Ace’s wife.


City of God (Fernando Meirelles, Kátia Lund, 2002)

With one of the bleakest tagline in recent memory — “If you run, the beast catches you; if you stay, the beast eats you.” — City of God depicts the growth of organized crime in Cidade de Deus suburb of Rio de Janeiro in the 1960s through to the 80s. The film is narrated by Buscapé (Alexandre Rodrigues) who, throughout his life, cannot escape the overwhelming influence of rival gang leaders Li'l Zé (Leandro Firmino da Hora) and Mané (Seu Jorge). Yes, that Seu Jorge — the handsome Team Zissou member singing David Bowie songs in Wes Anderson’s The Life Aquatic. Don’t expect another ukulele rendition of “Changes” in City of God though.


Election I & II (Johnnie To, 2005 & 2006)

Much like The Godfather and its follow-up, Hong Kong filmmaker Johnnie To’s Election and its 2006 sequel are both staggeringly good (and the sequels are just a little bit better). Starring Tony Leung Ka-fai, Simon Yam, and Louis Koo, Election focuses on the power struggles within Triad societies — Hong Kong’s equivalent of the mafiosa — during an election process for the new head of the Wo Shing society. The film’s brutal, gorgeous, sometimes funny, and everything you’d need in a gangster film.


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