Crime Doesn't Pay - Rotten Tomatoes
Unlike a lot of the bumbling criminals on this list, you can't fault Dignan (Owen Wilson) for being underprepared. In fact, perhaps he's planned out his big score a little too thoroughly ("Here are just a few of the key ingredients: dynamite, pole vaulting, laughing gas, choppers -- can you see how incredible this is going to be?"). Unfortunately, Dignan's co-conspirators, Anthony (Luke Wilson) and Bob Mapplethorpe (Robert Musgrave), are significantly less enthusiastic about his criminal ambitions, and his mentor, the sinister Mr. Henry (James Caan), may have ulterior motives.