These 5 best comedy heist movies maintain a fine balance in order to work for audiences. The protagonists are criminals, which makes them, by definition, somewhat unsympathetic characters, so, some redeeming and endearing traits are necessary. There has to be some danger and suspense, but, the situations can't be dangerous enough to ruin the fun. These 5 best comedy heist movies manage to bring together great stories and characters to make exciting and enjoyable watching experiences:
- "A Fish Called Wanda". John Cleese, Jamie Lee Curtis and Kevin Klein all turn in fantastic performances in this classic comedy heist. Curtis's character's foreign language obsession leads to some of the movie's best dialogue, plus an unforgettable dancing scene performed by Cleese.
- "Lock, Stock and Two Smoking Barrels". In one of Guy Richie's best movies, a group of bar buddies get themselves further and further over their heads with a series of "can't miss" schemes, including a robbery that should be a piece of cake. It can be hard to follow the movie's many twists and turns, but that just makes it even more fun to rewatch.
- "Ocean's Eleven". Both the original and the remake deliver great dialogue and amusing twists. If you're on an "Ocean"'s kick, give "Ocean's Twelve" a miss, but check out "Ocean's Thirteen". It's arguably the funniest of the bunch.
- "The Maiden Heist". When the distributor went bankrupt, it prevented this film from getting the wide release it deserved, but, "The Maiden Heist" is well worth seeking out. This museum robbery movie is one of a comedy heist is worth watching for its cast alone, which includes William H. Macy, Christopher Walken, and Morgan Freeman. The highly comedic scenarios and surprisingly touching ideas about beauty, art and aging all make it even better.
- "After the Sunset". It's sort of amazing to ponder that Pierce Brosnan never played a jewel thief before appearing in "After the Sunset". The role seems made for him. The cat and mouse game he plays with Woody Harrelson involves a lot of clever dialogue and some extremely funny physical comedy. Salma Hayek is beautiful and magnetic as ever as Brosnan's lover and accomplice.