Oh man.. So many come to mind..
Kentucky Fried Movie (70's or so, bunch of skits that were great, excellent 70s era natural bewbs shown)
Envy (Jack Black, and Ben Stiller, funny ass weird movie must've went straight to DVD)
The Holy Land (Another $2 from Blockbuster special, good luck finding this one.. It's about a hasidic jew falling in love with a suicide bomber, or something like that.. yeah)
Anything by Wes Anderson - Darjeeling Limited, Life Aquatic, Royal Tennenbaums Rushmore, Bottlerocket - these movies must be viewed numerous times to really appreciate how ridiculous they are.