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The Greatest Heist Comedies of All-Time

Written by on August 23, 2017 

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There’s nothing revelatory or new about adding a dose of the comedic to a crime picture, but the heist comedy is just a small corner of a vast and beloved cinematic landscape, as of recently, dominated by one filmmaker: Steven Soderbergh.

Responsible for four acclaimed entries in the genre, including Out of Sight and the Ocean’s 11 trilogy, Soderbergh has thankfully ended his so-called retirement and returned to film and the world of heist comedies with his newest, Logan Lucky, now playing in theaters. The film’s plot follows Jimmy Logan (Channing Tatum) a family man who plans to rob the Charlotte Motor Speedway in North Carolina, only to find he and his crew (Adam Driver, Daniel Craig and Riley Keough) must do the job while a NASCAR race is underway.

To celebrate Soderbergh’s return with Logan Lucky, we’ve decided to look back at the greatest heist comedies of all-time. Please enjoy and suggest your own favorites in the comments.

A Fish Called Wanda (Charles Crichton and John Cleese)

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Often, the hardest part of a heist is not the execution of the robbery, but getting away with the money. In A Fish Called Wanda, a hilarious crime caper from the mind of Monty Python member John Cleese and Ealing Studio veteran Charles Crichton, the heist is a success, save for the arrest of one member of the crew, the only one who knows the location of the diamonds. While Wanda (Jamie Lee Curtis) tries to seduce their defense lawyer (Cleese) in the hopes of finding the loot, the animal-activist Ken (Michael Palin) attempts to kill the only eye witness to the heist. Soon, the crew’s plan spirals out of control, ensuing burglaries, divorces and even few dead fish before they ever get their hands on the diamonds. Finding humor in the twisted personalities and moral bankruptcy of its characters, A Fish Called Wanda delivers a biting, nasty comedy classic, a film well aware that it’s more fun to laugh at jerks, albeit lovable ones.

After the Fox (Vittorio De Sica)

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Akin to cinematic candy, Vitorrio De Sica’s After the Fox is an aggressively ridiculous farce from screenwriter Neil Simon, which skewers the heist genre by way of the old film-within-a-film gag, turning the arrogance and vanity of its characters into dazzling comedy. Peter Sellars plays Aldo Vanucci, known as The Fox, a daring international thief capable of breaking out of any prison in the world. Planning to smuggle a shipment of stolen gold into Europe, Vanucci and his team disguise themselves as filmmakers, shooting a neo-realist film in a small coastal town. The heist plot is merely employed as clothesline upon which Simon, co-screenwriter Cesare Zavatinni and Sellars to hang their hilarious material. You can get a glimpse of the film’s tone in the world-weary exchange between aging movie star Tony Powell (Victor Mature) and his agent, played by Martin Balsam: “What’s neo-realism?” “No money,” the agent replies.

Bottle Rocket (Wes Anderson)

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Wes Anderson’s feature debut, the slyly comedic Bottle Rocket, positions its heroes, three young wannabe criminals with an eye for small-scale robberies, as blind innocents, lost in the unfamiliar world of adulthood. As part of his 75-year plan, Dignan (Owen Wilson) forms a gang, consisting of himself, Anthony (Luke Wilson) who’s fresh out of a voluntary psychiatric hospital, and Bob (Robert Musgrave) who becomes the getaway driver simply because he has access to a car. Their dreams of criminality stem from a boyish sense of boredom and malaise, inspiring them to cross the line into what they think of as a life of crime. After their maiden heist at a local book store, the gang hits the road, hiding from the law that clearly isn’t chasing them: “On the run from Johnny Law,” Dignan says. “Ain’t no trip to Cleveland,” a touchingly quaint portrait of lost youth.

The Dion Brothers, or The Gravy Train (Jack Starrett)

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A whimsically Southern take on the heist film, The Dion Brothers follows the two titular rednecks (Stacy Keach and Fredric Forrest) in their plans to rob an armored car. With the money, they hope to open the fanciest seafood restaurant in Washington D.C., where they’ll rub elbows with the politicians and socialites, or at least, that’s the dream. Their innate vulgarity and crassness dooms their aspirations, while their lack of self-awareness still pushes them to move forward with the robbery, an air of dread hanging over the entire operation. When the heist goes awry, the Dions are left running for their lives, pursued by police as they fight to get out with their money. Co-written by an uncredited Terrence Malick, the film has the distinction of being one of Quentin Tarantino and David Gordon Green’s favorite films.

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