Successfully pulling off "dumb movie criminal" isn't as easy a task as one might believe. Pulling off dumb is quite easy but unless the dumb criminal is surrounded by good writing, directing, and acting the whole thing falls apart (see: certain Tom Green and Queen Latifah vehicles). In my book the criminal either needs to be lovably dimwitted, humorously deranged, juxtaposed against witty straight men, or a combination of all three.
I think the following collection represents that. It also represents that the Coen Brothers have mastered the art of dumb criminal.
The odyssey of everyone's favorite 1930's escaped Mississippi convicts is beyond brilliant. "Damn, we're in a tight spot" is the official motto of dumb criminals everywhere as far as I'm concerned.
Kevin Kline was so good as pseudo intellectual Anglophobe Otto in A Fish Called Wanda he won an Academy Award. Hating the English and yelling "@sshole!" a lot will do that. The clip below sums that up nicely but has some NSFW audio.
How Out of Sight doesn't have a stronger cult following I'll never understand. It's Clooney at his Clooniest and Don Cheadle absolutely kills it as ex-boxer turned thug criminal leader Snoop Miller. Steve Zahn's Glenn also gets honorable mention on this list. Not to mention it's the only thing Jennifer Lopez-related that I will ever fully endorse.
Below video is awesomely NSFW. "The man just doesn't have to die, Foley. He could fall on something hard..."
Just writing about Lock, Stock makes me sad that part of Guy Ritchie's pre-nup with Madonna involved sacrificing three-quarters of his genius (no family members can be more than half as genius as Madonna, you see). Anyhoo, when the boys get taken in a high stakes game of three card brag it kicks off a series of superb criminal hijinks, and turns Jason Statham into Jason Stathom. You're welcome, world.
I can't get my head around this being the same guy whose last three movies were Sorcerer's Apprentice, Season of the Witch, and Drive Angry 3D either.
If the old "fake kidnapping the wife" scheme has gone worse for anyone in the history film than William H. Macy's Jerry Lundegaard I'm not aware of it. "Aw what the Christ?"
Quick Change is one of a handful of Bill Murray movies that don't qualify as top tier but that I find uber enjoyable, much in part to the killer cast (Tony Shaloub was born to play a cab driver). Randy Quaid's Loomis makes a terrific foil for Murray's Grimm. Randy Quaid would almost definitely rob a bank with you for real today, however I don't think it would be as much fun.
It's hard not to like the criminals or the movie when the premise centers around the bank robbery cover cookie business becoming a huge success even though the bank robbery itself is an epic failure.
Another underrated film, part of a string of good stuff from Brad Pitt after he vowed never to make anything as crappy as Meet Joe Black again. The "Little more Mexican" scene below pretty well sums up why this flick is underrated.
Continually shaking down the Dude for cash is beyond brilliant. "Oh, I know that guy, he's a nihilist." Gawd I love the Coen Brothers.