A musical comedy con game: The Music Man.
Now that family-friendly caper comedy movies have been broached, Disney put out quite a few in the '60s & '70s. For example:
That Darn Cat!
The Apple Dumpling Gang
No Deposit, No Return
Candleshoe
Comedy, with music, and multiple capers: O Brother, Where Art Thou?
Courtroom comedy with defendants mistaken for caper culprits: My Cousin Vinny.
I think you should give Bedtime Story a try, with David Niven and Marlon Brando.
I don’t remember Three Kings having much humor in it at all. There was some banter at the beginning (“Is this the proctology tent?”) but the movie got serious very fast and stayed that way until the end.
Marvel’s Ant Man was funny throughout and is a heist movie.
What’s wrong with the remake of The Italian Job? I thought it was a great cast, good humor throughout and lots of action.
Ehh, not really a caper/heist since the two “yoots” were charged with murder – unless you count their plot to shoplift a can of tuna. 
:dubious:
Dude, they blew up a cow.
The scene where the reporter, Adriana Cruz (Nora Dunn) chases Walter (Jamie Kennedy) around while driving a jeep screaming “where is he, bitch?” is hilarious.
Also:
Archie Gates: Sit down. What do you see here?
Chief Elgin: Bunkers, sir.
Archie Gates: What’s in them?
Troy Barlow: Stuff they stole from Kuwait.
Archie Gates: Bullshit. I’m talking about millions in Kuwaiti bullion.
Conrad Vig: You mean them little cubes you put in hot water to make soup?
Archie Gates: No, not the little cubes you put in hot water to make soup.
And:
Troy Barlow: I’m gonna buy a set of Lexus convertibles in every color.
Chief Elgin: I told you, Lexus don’t make a convertible.
Troy Barlow: I’ll bet you a Lexus they do.
Chief Elgin: Alright, but it won’t be a convertible.
Also:
[Walter’s wearing night-vision goggles in broad daylight]
Troy Barlow: Hey, would you take those fucking things off?
Walter: I never got to use night-vision.
Troy Barlow: They do not work during the day!
Walter: Yeah, they kinda work.
This movie is by turns hilarious, deadly serious and as tense and intense as a room full of people holding hand grenades without pins; it’s one of the best war movies ever made IMO.
I nominate : A Fish called Wanda & Fierce Creatures
*The In-Laws*with Peter Falk as an undercover CIA operative with a son planning to marry a super-conservative dentists daughter (Alan Arkin). Hilarious action with South American warlords.
Let me guess, you simply read the title and skipped “Courtroom comedy with defendants mistaken for caper culprits”?
IOW: I know it’s not really a caper/heist movie. It’s a courtroom movie which explores what could happen if a caper/heist goes bad where people with a similar appearance to the culprits had been minutes earlier.
The one Woody Allen movie I’ve watched entirely, not in bits and pieces, and in turn REALLY liked, more than fits the bill here: Small Time Crooks
I’l go so far as to say the remake is much better than the original. I put the original The Italian Job and Butch Cassidy and the Sundance Kid in the same category. They are remembered as being a LOT better than they really where. Or, more accurately, they don’t hold up well under the test of time and people remember them as being a lot better than they were.
“Serpentine! Serpentine!”
Also see Take the Money and Run. Good stuff.
Tower Heist was a pretty good heist comedy.
I found it to be totally forgettable. I can hardly remember a single thing about it, except that most of it was set in America, which makes the title itself pretty silly.
Heist
Safe Men
Happy, Texas
Welcome to Collinwood (a remake of Big Deal on Madonna Street)
I remember a couple of things about The Italian Job. First, it was like a commercial for the Mini-Cooper. Second, I got to look at Charlize Theron for about two hours.
Agree with others that Quick Change is one you need to see.