In no particular order:
Smokey and the Bandit
Caddyshack
History of the World Part I
Monty Python and the Holy Grail
Strange Brew
South Park Bigger, Longer and Uncut
Clerks
Chasing Amy
Dogma, and...
Fight Club
(yes, Brad Pitt and Edward Norton, the first time I watched it I thought what a great drama, once I got the joke I immediately watched it again and LMAO)
Fight Club did have some funny moments. The girlfriend’s comment after sex, well, I can’t post it on FR, but you remember.
I'll second this one; it deserves a better showing in this thread.
"The jig is up!!"