We have our usual suspects of more recent cinema like Being John Malkovich and older "cult" classics such as Rocky Horror Picture Show or for the cine-nerd THX 1138.
Theres a few gems out there of strange movies made for weird folks. Here's a few that may have missed Just my top 5 fucked up movies.
1/ Blue Velvet (1986):
Wow where do I start. Quick summation. Man finds a severed ear in a field, tries to figure out how it got there and gets sucked into the evil underbelly of his local town.
Time travel and strange people who dress in metallic bunny masks.
3/ Repo Man (1984):
awesome punk rock sound track, young man becomes a repo man. A repo notice goes out on a car that happens to have a dead alien in the trunk and a slowly dying government scientist (who is also slowly going crazy).
4/ Time Bandits (1981):
young boy travels through time and dimensions with a group of dwarves intent on looting.
5/ In the Mouth of Madness (1994)
An H.P. Lovecraft inspired film by John Carpenter. A book that apparently causes people to go crazy, problem is the places mentioned in the book exist. Or do they? Muhahhahahahaha.
honorable mentions- (with some interesting links)
he Wizard of Oz ( and the "soul" version called The Wiz is a must see) apparently can be synced to Pink Floyd's Dark Side of the Moon. There's a whole group of people out there who spend time and money syncing iconic albums with movies saying they mesh. Dunno but sounds neat.
Rocky Horror Picture Show, any given Tarantino film, Doctor Strangelove, Hellraiser, A Clockwork Orange, Naked Lunch, Monty Python movies, Sleepaway Camp, Requiem for a Dream, One Hour Photo (probably the best thing Robin Williams ever did) , Harold and Kumar movies, Jay and SilentBob, Drug Store Cowboy, Jacobs Ladder, Kentucky Fried Movie.
If I missed any you feel needs to be considered let us know. If I haven't seen it then I just might. -EvS