The 25 Best Crime-Comedies

Crime should be no laughing matter. Movies like The Godfather, Scarface, and L.A. Confidential revel in crime's capacity for destruction and moral corruption. But spend any time reading news of the weird and you'll see that, with the correct perspective and distance, illegal activities can be hilarious—desperate people doing desperate things, and with awful results. Thus, the crime-comedy.

This Friday, a new film joins the genre. Stand Up Guys, starring, Al Pacino, Christopher Walken, and Alan Arkin, revolves around betrayals and hired killers, but with the light touch directors like the Coens and Tarantino have perfected. Stand Up Guys might not prove to be one of the genre's enduring works, but it does offer the perfect opportunity to talk about the 25 Best Crime-Comedies.

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As a series, the Ocean’s franchise is no real thing of beauty, but don't let that tarnish the reputation of the first installment, which is, admittedly, pretty damn fresh. Steven Soderbergh's cool eye and a cast of greats, including George Clooney, Brad Pitt, Matt Damon, and Don Cheadle, gave this movie more style than a glossy GQ cover.

The plot, you may remember, revolved around Danny Ocean recruiting a squad to help him rob the Bellagio, The Mirage, and the MGM Grand in Las Vegas—at the same damn time, of course. It was pure Hollywood, but also vintage Hollywood—the dialogue was sharp, but flowed from the actors like smooth silver.

And then the franchise turned into a mess no one could salvage. We'll always have Eleven, though.

The ‘80s were a highpoint for crime-comedies, and director Frank Oz delivered one of the decade's classics with Dirty Rotten Scoundrels. Starring Steve Martin and Michael Caine as con artists swindling their way through the French Riviera, DRS works in large part because of their perfect performances.

The bloodless crime element takes a backseat to the comedy here, following in the tradition of The Sting, and other character-driven, joke-heavy caper comedies.

In this classic Audrey Hepburn comedy, the beloved star plays the daughter of a man who forges famous paintings and statues for a living. After Daddy sells a fake statue of Venus to an art collector, he’s horrified to find out that, in the small print of the contract, the buyer has demanded it be inspected by an expert.

Worried that her father will be publicly exposed as a forger, Hepburn's character enlists the help of a thief who once tried to rob her house to help her rob the statue back from the museum.

Hijinks ensue during the screwball attempts at stealing of the statue back from the museum. Though it’s not the most sophisticated or sharply-written crime-comedy ever made, Hepburn is undeniably charming, fueling the fun in this playful riff on the heist flick.

Don't act like you didn't howl through Robert De Niro and Billy Crystal's mob farce when it hit theaters. Unfortunately, De Niro has starred in so many misguided comedies since this movie, the reputation of all his lighter work has been thoroughly tarnished. Still, his neurotic mobster works.

Don't dwell on the plot, which sleepwalks through the crime clichés like assassination attempts, bodies in car trunks, hovering FBI agents, and the like. Just bask in the light of a Bobby De Niro that seemed poised for a glorious rebirth as a comedic actor.

Color us surprised—Richard Linklater’s Bernie is so dark and wildly funny that it trumped nearly every other comedy in 2012. Jack Black plays Bernie Teide, a real-life mortician who kills the wealthy widow that he recently befriended. But Teide isn’t caught right away; instead, he makes excuses to the townsfolk as to why she's no longer around, and uses her large fortune to donate to people in need. When Teide is put on trial, the town comes to his defense, claiming that the old woman was hated by everyone and deserved to die.

More than a pitch-black comedy, Bernie is a study in perception, and how people view murder when it’s perpetrated by someone they like against someone they despise. It also contains the performance of Black's career.

The ‘90s and early 2000s were a time of greater misses than hits for Woody Allen, with Small Time Crooks acting as a welcome exception. Allen's character Ray, his wife, Frenchy (Tracey Ullman), and their friends (Michael Rapaport and John Lovitz) buy a restaurant that they convert into bakery to sell cookies. But that business is only a front, as their real plan is to tunnel from the basement into a nearby bank vault.

Since this plan requires Woody Allen to perform manual labor, it's no spoiler to say that the tunneling operation fails spectacularly, even as the cookie business turns out to be huge. It’s an oddball premise that's reminiscent of the director’s earliest work.

An adaptation of an Elmore Leonard's novel of the same name, Get Shorty came out during a time when every studio was searching for the next Pulp Fiction. Like Tarantino, Leonard writes incredible dialogue, but his approach is more classic when it comes to story. In other words, he's not a kid who grew up in a video store, and despite the shots this film takes at Hollywood, it's not looking to deconstruct anything. It's just good.

John Travolta stars as a mob leg-breaker named Chili Palmer who'd love to rid himself of his underling position, but with a string of incompetent bosses above him, is convinced he’ll never get out.

However, after he goes to Vegas to collect some money from a deadbeat B-movie producer from Hollywood, he pitches him a movie idea and quickly finds himself in show biz. The movie serves up its fair share of twists and turns, but it always manages to be engaging. It’s not often that we see members of the mob portrayed as such sad sacks, yet it completely works here. The deadpan humor, mixed with the notion of an enforcer-turned-movie-producer, is more than enough to make Get Shorty stand out.

Shot through with dark Scottish wit and guided by the manic hand of director Danny Boyle, Trainspotting shines a wry light on the small-time drug dealers and addicts of Edinburgh. There's no specific score, no job to be pulled, just the grim-yet-comic details of life as a junkie.

Everyone in Trainspotting is either a user, dealer, or a thief, and they all aim to sell enough drugs or steal enough money to be able to afford their addictions. Of course, nothing works out. Characters OD, shit flies, and one toilet in particular sees too much action. When people talk about Danny Boyle's gifts, they're talking about Trainspotting.

Meet Professor Marcus, a gentleman rents a room in a house owned by an eccentric old woman. Disguised as a musician, he tells her that his friends will routinely come in and out with their instruments to rehearse. Only, they aren't rehearsing anything—they're pulling a heist.

The cast of the original The Ladykillers—not to be confused with the Coens' misstep—features comic greats like Alec Guinness and Peter Sellers, filling the picture with the kind of British humor that borders on the insane.

A send-up of pulpy detective stories, Kiss Kiss, Bang Bang stars Robert Downey Jr. as a career thief who inadvertently stumbles into a movie audition, only to find himself cast as the star. To research the role, he begins to shadow a real private eye. And then they stumble upon a murder, and things really get frantic.

Downey's self-aware narration provides humorous distance for the madcap situations unfolding onscreen. It's postmodernism-lite, and a lot of fun.

A throwback to '60s cotton candy-colored capers like Charade, Steven Spielberg's Catch Me If You Can is a light and quirky romp about identity and—obviously—fathers and sons. Leonardo DiCaprio plays Frank Abagnale, a young con man making millions through sheer charm and street smarts. On his tail is FBI agent Carl Hanratty, played to perfection by Tom Hanks.

These two bring a deadpan hilarity to a cartoonish ‘60s. Hanks, in particular, keeps the chuckles coming by playing Hanratty stiffer than a taxidermied deer. He just can’t understand how this 19-year-old swindler keeps getting the best of him. He's frustrated, the audience is charmed, and DiCaprio gets to steal another movie.

Through all its misery and crudeness, it’s easy to forget that Bad Santa is really a comedy at heart. Billy Bob Thorton is the titular department store Santa, an alcoholic who takes scores with a partner named Marcus; the pair works malls in order to rob them. It's a Christmas movie for the jaded masses.

Unlike a lot of crime-comedies, Bad Santa is character-driven rather than obsessed with the nuts and bolts of the scheme. You don't watch for the ingenuity of the plan, you watch because Santa is harassing women, drinking heavily, and vomiting. Director Terry Zwigoff is the master of the misanthrope, and there are very few crime-comedies that can match the cynicism of Bad Santa.

After retiring his timeless Little Tramp character, Charlie Chaplin surprised audiences everywhere in Monsieur Verdoux by playing a criminal who marries wealthy widows and then murders them for their dough. It’s not often that murder is a laughing matter, but Chaplin is forever a master—turning such a repugnant human being into a star remains one of his most impressive accomplishments.

Chaplin performs all of the physical gags from his Modern Times and Great Dictator days, but here they're accomplished with poison in his hand and malice in his heart.

Wes Anderson's droll debut introduced viewers to a group of characters, notably including Luke and Owen Wilson, who have absolutely no idea how to pull off a heist. Problem is, they really want to.

It probably wasn’t a great idea for a guy who just left a mental asylum (L. Wilson) to enter the world of crime, but you can't blame him for wanting to try something different. From the first scene, Anderson's fixation on composition and sand-dry jokes is made explicit. Audiences haven't been able to get enough since.

Oftentimes, when super-recent films make “Best Of” lists, it’s because they’re still fresh in people’s minds, but we’re predicting that Seven Psychopaths will be regarded as one of the great crime-comedies for decades to come. The premise is simple: Two losers (Christopher Walken and Sam Rockwell) kidnap dogs from all over L.A. and then claim the reward money.

Unfortunately, they steal a Shih Tzu named Bonny that belongs to a vicious gangster (Woody Harrelson) and things quickly spiral out of control.

The second film from masterful Irish playwright Martin McDonagh, Seven Phsycopaths was poorly marketed, meaning lots of people missed out on it last year—don't continue to make that mistake.

The Coen brothers have always worked aspects from multiple genres into their films, with Fargo being a prime example. Some may see it as a simply a crime drama, but that would ignore the supremely deadpan humor that twists the movie into something far more unsettling.

A pregnant police chief (Francis McDormand) is investigating a series of murders around the town of Fargo, North Dakota, while also following the exploits of a man (William H. Macy) who's hired two criminals to kidnap his wife. Peter Stormare and Steve Buscemi play the hired help, who couldn't be any lousier at their jobs.

The tragic pair brings humor out of the mundane macabre, like in the scene where they bicker like a married couple over how to split their newly-stolen car. Buscemi nurses a gunshot wound the entire time. Should you feel guilty about laughing? The Coens remain stone-faced, daring you to react.

In Raising Arizona, Nicolas Cage plays a criminal who falls in love with a policewoman, played by Holly Hunter, while having his mugshot taken. Unable to conceive a child together, and unable to adopt because of his criminal history, the couple decides to steal a baby from a fresh batch of quintuplets born to a wealthy furniture salesman.

This is as over-the-top as anything the Coens have ever made, full of bizarre characters and even stranger situations. A screwball comedy about a stolen baby—they just don't make 'em like this anymore.

Boasting one of the funniest casts in history, A Fish Called Wanda is a tale of crime and betrayal as the four participants in a jewelry heist all plot different ways to keep the loot for themselves. Everything comes unhinged via increasingly cartoonish stunts and set pieces, like Kevin Kline torturing Michael Palin by eating all the fish in his aquarium. Palin later responds by running Kline over with a steamroller. All of this is to say nothing of John Cleese prancing in his underwear.

Kline won an Oscar for his performance, but the entire cast shines. This is the epitome of new screwball comedy.

Every rough-and-tumble British gangster picture to find success in the states in the 2000s owes everything to Guy Ritchie's Lock, Stock and Two Smoking Barrels. This movie tells the story of a group of friends who try to rob a gang that lives next door after they lose a small fortune during a card game with another powerful crime boss.

Where's the comedy? It's all in the words. These are some sarcastic, mean-spirited sons-of-bitches who can't help but be hilarious, even when they're trying desperately to play the tough guys.

Martin McDonagh's first feature casts Collin Farrell as a a hitman who's accidentally killed a young boy during a job gone wrong. Along with his partner, he's sent by his boss to the city of Bruges where he is to await orders. To say more would spoil the surprises of one of the best-written movies of the last ten years.

Farrell is easily at his best here, especially during his fight against a drug-addled dwarf that signals the film's swerve into absurdist humor. In Bruges is so dark, it's nearly a tragedy. But the threat of tears make the subversive laughs all the better.

Not only is Take the Money and Run one of the earliest examples in the crime-comedy genre, it’s also one of the first full-fledged mockumentaries to ever hit the screen. Woody Allen's feature follows the life of Virgil Starkwell, a career bank robber, across his various sprees and stints in jail. Like most of Allen’s early films, the humor comes from classic slapstick and sight gags.

From asking a sheriff for sex advice while on a chain gang, to his ill-fated attempt at being a cellist in a marching band, Starkwell's misadventures form a collection of brilliant gags. The crime elements aren't as important as the straight-up laughs in this one, but that doesn't stop it from being one of the best.

A love letter to Raymond Chandler, The Big Lebowski is the funniest film in the Coens' body of work, a fact that can get lost among the fervent (and irritating) cult following it's attracted. The plot is all confusion, with mistaken identities, stolen rugs, pornography, bowling, Vietnam, lots of pot, and kidnapping. And embezzlement too, if memory serves. But the plot is just an excuse for quirky characters and incredible dialogue.

The Dude. Walter Sobchak. Donny. Jesus. No summary can contain all the wonders of The Big Lebowski, a film that confused the hell out of critics and audiences when it was first released. Though the cult is tired, we owe it thanks for saving the film from obscurity.

If this list teaches you anything, it’s that the British do crime-comedies better than anyone. In Snatch, director Guy Ritchie saturates every frame of the movie with the criminal culture, from thieves gunning to steal a rare diamond to a crooked boxing promoter (played by Jason Statham). And with a mix of A-list stars, like Brad Pitt and Benicio del Toro, and sleazy character actors, like Vinnie Jones and Dennis Farina, this movie brings cynical comedy to the world of organized crime.

What really makes Snatch stand out, though, is the style that Ritchie brought to it. Similar to Danny Boyle’s raw, filthy approach to the underworld, Ritchie’s quick cuts and innovative camera shots give the whole thing a twisted energy that most movies can only hope to recreate. Add in some sharp dialogue and memorable set pieces—like del Toro’s Hasidic Jew jewel heist in the film’s opening moments—and you have a crime-comedy that packs in some style, as well laughs.

One of the purest examples of the crime-comedy to ever hit the screen, The Sting is also a must-see for anyone interested in taking a tour through great works in Hollywood history. The story spotlights two professional grifters (Paul Newman and Robert Redford) who attempt to swindle a mob boss. The complicated plot these two hatch up is secondary to their chemistry on screen, as both bring an undeniable comedic charm to each con they pull off.

You can look at what director George Roy Hill managed in The Sting and confidently claim that this is the movie that began the whole crime-comedy genre as we know it today. Scenes like Newman's poker game with Lonnegan sum up the film's unique tone perfectly: It’s never too jokey, nor does it depend on blood and gore; it's simply a sharp, classy comedy that succeeds on the strength of a great script and even better performances.

Could any other movie have taken the top spot besides Pulp Fiction? Some people might not consider this a crime-comedy in the traditional sense, but when you deliver non-stop laughs while also showering audiences with robberies and murders on the screen at a rapid-fire pace, you fall comfortably into the genre in our opinion. From the opening scene with Tim Roth and Amanda Plummer making small talk before robbing a diner, to Jules and Vincent Vega executing some two-timing underlings, this movie is filled with banter and dialogue that isn’t just hilarious but highly quotable as well.

What makes Pulp Fiction work so well is that it is played completely straight; never once do you believe that the characters on screen are meant to make you laugh. But the quotes are so sharp and the actors are all so brilliant that it’s almost impossible to keep a straight face for more than five minutes. Even scenes as mundane as the one between Travolta and Uma Thurman at the 1950s-themed restaurant is brilliantly funny, simply because you have the criminal world juxtaposed with slice-of-life rants like you would see in Curb Your Enthusiasm.

Pulp Fiction is a movie that doesn’t neatly adhere to just one genre, but that doesn’t stop it from being the best crime-comedy that we have ever seen.