Many that I would've listed have already been. I will add my others and give my nods to those mentioned.
For yuck-yuck type "caper's", I will agree with Shell on "Maverick", very, very fun. I will add "Fargo" and as previously mentioned "Burn After Reading". I long ago had the hot's for Brad Pitt, not so much anymore, but he was what I laughed at the most, perfectly dumb.
I'll have to disagree with Daniel, I own and think the re-make of "The Ladykiller's" is a great caper film. I admit, I am an unabashed Tom Hanks fan but I think his performance was only so-so, and yet I still love the movie overall. If your sense of humor fit's with the movie, you'll love it.
For my contribution as far as "heist" film's go, I can't believe no one has mentioned "Reservoir Dog's". My second pick has already been listed, "The Usual Suspects". Both have small element's of humor but are for the most part serious. My third is "A Simple Plan" with Bill Paxton and Billy Bob Thornton. Not really a heist movie but along the same lines.
Lastly, I will nitpick Shell on "Bonnie and Clyde". It's been many years since I've seen Dunaway/Beatty's movie. There may be comic elements added into the movie but in real life, there was nothing comedic about the duo that were a public enemy. Maybe I need to watch it again, it might have been filmed as a "caper". If so, then my appologies Shell.
