What’s the key to pulling off a successful heist? Having a competent and quick-witted team, for starters. But, as many heist movies have proved, it’s not as easy as it looks. In the new black comedy Seven Psychopaths, Sam Rockwell and Christopher Walken play professional dog-thieves hired to snatch the beloved Shih-Tzu of a violent, angry gangster (Woody Harrelson) willing to do anything to retrieve his adorable pooch. Written and directed by acclaimed playwright Martin McDonagh (In Bruges), the impressive cast also includes Colin Farrell, Olga Kurylenko, Tom Waits, Abbie Cornish and Gabourey Sidibe.

Seven Psychopaths, which has garnered positive early reviews, opens October 12, but before you check it out, join MM as we take a look at some of the quirkiest heist teams in recent movie history.

Quick Change (1990)
directed by Howard Franklin and Bill Murray
Based on the book by Jay Cronley, Quick Change stars Bill Murray (who also receives his first and, to date, only directing credit for the film) as sardonic crook Grimm, who robs a bank with his partners in crime, girlfriend Phyllis (Geena Davis) and dimwit buddy Loomis (Randy Quaid). The movie’s memorable opening features Grimm sticking up a New York City bank dressed as a clown, much to the bafflement of the hostages. While the heist seemingly goes according to plan, the getaway turns into a nightmare, as Murphy’s Law prevents the thieves from getting to the airport and escaping. (It doesn’t help that a relentless police chief, played by Jason Robards, is in hot pursuit.) This goofy comedy is filled with hilarious physical humor and slapstick situations. And, of course, our quirky list would be remiss without the surreal sight of a clown robbing a bank.

Reservoir Dogs (1992)
directed by Quentin Tarantino
While Tarantino’s smash debut isn’t a comedy (unlike the other heist movies on this list), there’s no denying that the fast-talking thieves of Reservoir Dogs are pretty damn quirky. Heck, the movie opens with them discussing the merits of Madonna’s career. What makes Reservoir Dogs so ingenious is that it’s a heist movie… that never shows the actual heist. Instead, we see the bloody aftermath of a botched diamond robbery, as the surviving thieves begin to suspect that one of their crew is actually a police informant. Featuring a brilliant ensemble cast that includes Harvey Keitel, Steve Buscemi and Michael Madsen, Reservoir Dogs is a classic that’s lost none of its shock value (watch out for that notorious ear-splicing scene!) or originality.

Bottle Rocket (1996)
directed by Wes Anderson
This deadpan comedy marked the debut of idiosyncratic moviemaker Wes Anderson. The film centers around three slacker friends—Dignan (co-writer Owen Wilson), Anthony (Luke Wilson) and Bob (Robert Musgrave)—who devise an elaborate plan to pull off a simple robbery. However, the three of them, led by the idealistic Dignan, prove to be hilariously inept criminals. You know someone’s not made out to be a crook when they rob their own house as practice. The central set piece of the film—in which the guys attempt to rob a safe at a storage facility—is a perfect example of comic escalation, with the situation hilariously going from merely bad to outright disastrous. With its likable cast (also including James Caan as a cunning businessman), Bottle Rocket remains as sweet and funny as it was 15 years ago.

Palookaville (1996)
directed by Alan Taylor
Like Bottle Rocket, the New Jersey-set Palookaville is about three ordinary guys (played by William Forsythe, Vincent Gallo and Adam Trese) struggling (and failing) to become successful thieves. A key example: The movie opens with the gang attempting to rob a jewelry store at night only to realize that they’ve made a mistake and have actually broken into the adjacent shop, a bakery. Once they hatch a scheme to rob an armored car, things get even worse. With its eclectic cast (which also includes Frances McDormand as a local prostitute) and offbeat sense of humor, Palookaville is a lot of fun, and it never loses sight of the three good-hearted, likable losers at its core. Director Alan Taylor has since gone on to become one of the most sought-after directors in television, helming episodes of such notable series as “The Sopranos,” “Mad Men” and “Game of Thrones.”

Three Kings (1999)
directed by David O. Russell
In this gritty dramedy, George Clooney, Mark Wahlberg, Ice Cube and Spike Jonze (director of Where the Wild Things Are) star as four soldiers who attempt a gold heist at the end of the Gulf War. Along the way, the unlikely quartet encounters a group of Iraqi rebels in desperate need of their help and decide to make a heroic journey to help them reach the Iranian border. By turns funny, disturbing and unexpectedly moving, this unconventional heist movie effortlessly transitions from dark comedy to gory action-thriller to uplifting drama.

Welcome to Collinwood (2002)
directed by Joe & Anthony Russo
This caper comedy is a remake of Mario Monicelli’s 1958 Italian classic Big Deal on Madonna Street (also a major influence on Palookaville). The story concerns five small-time crooks (living in the Collinwood neighborhood of Cleveland) who try to organize one last big score. The impressive cast includes William H. Macy, Sam Rockwell, Patricia Clarkson, Luis Guzmán and, in a cameo role, the movie’s producer, George Clooney, as a retired safecracker (his grizzled performance here is the opposite of the smooth operator he plays in the Ocean’s Eleven series). Directed with a light touch by Joe and Anthony Russo (who’ve since helmed some of the best TV comedies in recent years, including “Community” and “Arrested Development”), Welcome to Collinwood is a funny, quirky little movie that did little box office in its theatrical release but is still worth a second look.

Have a fave movie heist team that didn’t make the list? Let us know in the comments!

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