Here's a list of movies that tickle programmers, with their (programmerly) commentary on them):
Laugh 'Til You Pee in Someone Else's Pants:
Airplane! - routinely tops "funniest movie of all times" lists, and routinely places in "best movies of all times" lists. It will ruin the entire gritty self-important melodramatic 1970s big-star disaster flick genre for you. "You can let yourself out the back. There's juice in the fridge."
God of Cookery - Steven Chow's mind boggling Hong Kong style Iron Chef.
Fierce Creatures - John Cleese (et al from A Fish called Wanda). In order to make a profit a (former) petting zoo must house only fierce creatures. Excellent British-like humor.
DarkstarFirst feature by JohnCarpenter?. Definitive SF parody. "congratulations, you have chosen to clean the lift. Please stand clear of the explosive bolts."
WagTheDogPolitical satire with Robert Di Niro and Dustin Hoffman
Raising Arizona an early Coen Brothers film. Wacky funny, but pales in comparison with The Big Lebowski
The Big Lebowski a hilarious bowling film by the Coen Brothers. Every time you think you know where it's going, it heads in another direction completely.
O Brother, Where Art Thou? The Coen Brothers take on a jail break. Very funny and a great soundtrack.
The Pink Panther Strikes Again(uneven, but the "questioning of the estate staff" scene is rather hilarious and perhaps worth the price of admission, alone; many other amusing scenes, just a little more tiredly acted than the former) http://www.rabbitw.com/wavs/panther/clous004.wav
Dogma (Don't miss the cameo by Betty Aberlin of MisterRogersNeighborhood?!)
ClerksMovie (anything by Kevin Smith exceptJay and Silent Bob Strike Back. Goddammit, that was terrible.)
TheGodsMustBeCrazyStarts off with very dry humour, but had me rolling in the aisles later. Some (Bill Cosby) thought it was racist, but that's pretty narrow-minded.
The Iron Giant <-- a brilliant lampoon of the ColdWar hardware fetish (trivia bit: based on 'TheIronMan?', a book by Ted Hughes, who was British Poet Laureate and Sylvia Plath's husband.)
Wait for Cable:
Charlie's AngelsA helplessly camp big-screen adaptation of that popular TV show, The Power Puff Girls.
I disagree - this is a wonderfully funny, while campy (sor of like StarWars, or maybe SpaceBalls? in that, eh?) movie definitely worth renting.
Don't Listen to the Critics:
Chasing Papi this poorly-named tidbit was widely panned as a bad sitcom full of latina stereotypes, like watching Telemundo or Univision. I find those comedies insipid and I found this a delightful antidote. It sets up all the typical tired "cat-fighting over a hunk" themes and twists them to attempt to show character development. "Attempts" being the operative word, but the ensemble acting (yes, real ensemble acting & not clever editing) and the minor pratfalls between the major attempts are a scream. During a moment of reflection on one woman's life story we see an insert of another woman listening intently. But her toy dog picks that moment for an enormous yawn.