Seen this movie a couple handful of times and it is still funny (just watched again tonight). What are the movies that turn your crank like this one turns mine? I'm looking for funny movies that can use repeated viewings.
Scott Pilgrim vs The World is on my list, though I am led to believe there are some people out there that didn't like it (heathens). Also: Doctor Strangelove and anything by the Marx brothers.
Unfortunately, most of popular Python has become so oft-quoted as to ruin it for me. I still find much enjoyment in the lesser known stuff, though, primarily because I either haven't seen it before, or I've only seen it a few times (the shock value is higher).
The Princess Bride seems obvious to add to the list, though it's perhaps been seen by me a few times too many at this point. Once you have an entire film memorized, you should probably pick up something else.
My little brother was obsessed with A Christmas Story one summer when he was little, and watched it at least once a day for around a month. Despite this, that movie still makes me laugh. It holds up pretty well, all things considered.
Most of the films I've watched again and again, apart from the one's already mentioned and the one that is the title of this thread, are Jane Austin-y or musicals. So I guess I'll leave it at that.
The Life Aquatic With Steve Zissou. If you appreciate the movie's foundational gag, it stands up extremely well to multiple viewings. It's even better if you enjoy the music of Devo and Bowie.
I generally hate watching any film more than once, unless I put at least a couple of years between viewings. Exception to that rule: Kiss Kiss Bang Bang.
@Morac: I agree about Python. I think the Holy Grail stands up better than Life of Brian though, because people only qoute a couple of bits maybe?
The Big Lebowski's already been mentioned, but I would also throw O Brother, Where Art Thou? into the ring. The "...And people who say we come descended from mon-kays!" line always kills me, without fail.
I'm no doubt breaking the rules here by sidling into the world of television, but I could happily watch Yes Minister and Yes Prime Minister on continuous loop for weeks without ill effect.
Well, I'm not much of one for a lot of comedies and most of my favorites have already been listed, but I find Snatch is always good for a laugh - very quick dialogue and ridiculous scenes. More recently I must admit that Your Highness was stupidly amazing and holds up much better than it should.