So many good contenders:
Donnie Darko
Repo Man
Fight Club
Time Crimes
Harold and Maude
A Clockwork Orange
Andy Warhol's Dracula
Fear and Loathing in Las Vegas
Heathers
Dead Ringers
Man Bites Dog
I only saw part of these two movies, but they looked weirder than anything I listed above:
Being John Malkovich
some japanese movie that was so weird that I couldn't figure out what it was about, except that it eventually is about the end of the world. Don't know the title.
Good decisions come from experience. Experience comes from bad decisions.