My favorite caper films have already been covered, so I’ll mention another book instead:
Bridge of Birds, by Barry Hughart. It’s a sort of ancient Chinese fantasy adventure, but it features several hilarious capers planned by Master Li (a sage with a slight flaw in his character) and related by Number Ten Ox (his client and muscle).
No, he’s not a con man. He never has an ulterior motive and he never misrepresents who he is or what his intentions are.
He’s an unlikely and unorthodox sheriff, but there is no “con” anywhere in the movie.
Having rewatched both of those films recently, I disagree 100%. The remake of Italian is a particularly tedious, joyless experience (when it’s not being overtly stupid).
Now, I will agree with your argument if applied to the original Ocean’s 11 (and to a lesser degree, The Thomas Crown Affair). I prefer the remakes of both.
Looks like we’ve moved away from “heist” films to con game comedies in general, so the granddaddy of them all–often duplicated, never equaled–is Ernst Lubitsch’s magnificent Trouble in Paradise, officially the best movie to now appear in this thread.
Also worth mentioning (it was on TCM this morning) is the bank robbery caper Larceny, Inc., a reminder that Edward G. Robinson was terrific at comedy, too.
Support Your Local Gunfighter, OTOH…
That is without a doubt the wrongest thing I’ve read today, and I’ve been reading Trump’s internet postings!
I agree, Support Your Local Gunfighter is the con job movie.
If you want to count TV, damn near every episode of all four seasons of Blackadder, plus the specials. Bald-faced con jobs and funnier than a rubber crutch. Plus Baldrick!
First movie I thought of was The Pink Panther–one of my favorite movies, ever since seeing it when I was 10.
Shoot 'Em Up is funny, but does qualify as a “caper/heist” film?
Would Miyazaki’s The Castle of Cagliostro count enough as both “caper” and “funny”?
If those don’t work then, technically, it’s also sort of the only Castlevania movie.
I suggest “Capers”, which is also know as “The Brooklyn Heist”. That right there tells me you were meant to see this movie.
A poker buddy of mine wrote and directed it. I was half terrified to attend a screening, simply because I am a pretty tough audience for comedy. BUt I knew that my buddy was a very funny guy, and I ended up very pleased with the film. I was just reading some of the imdb reviews and was pleased to see that other people really loved it and appreciated the creative and off-the-wall aspects. It won the jury prize for comedy at a Florida film festival.
So check it out.
Widow’s Peak Widows' Peak (1994) - IMDb You have to watch it all the way to the end to get it though.
Really leans a bit more to caper than comedy, but still…
Burn After Reading almost fits in this category.
I really liked Once Upon a Crime.
Another funny and unusual one is The Maiden Heist, starring Morgan Freeman, William H. Macy and Christopher Walken as art museum guards, each of which is obsessed with a particular painting or sculpture. They decide to steal the art (replacing them with forgeries) when these pieces are to be shipped off to another museum.
Caper, not heist, and based on a true story Sea Wolves.
Which, by the way, is great. This is a genre I’m apparently even less knowledgeable about than I thought. 
Hey–wanted to thank you for this recommendation. It’s the first film listed here that I was able to get my hands on and I really enjoyed it. The pacing’s a bit weird but that adds to it.
You’ve only seen one Woody Allen Movie?! Really?
You should see one from when he was funny, like before 1978.
I cannot second/third/millionth time enough! It was immediately what I thought of. It’s part of a perfect Bill Murray trifecta consisting of What About Bob?, Groundhog Day and Quick Change.
The plot and the pacing weren’t the movie’s strengths. It relied on the charisma of its performers and they delivered.