Originally Posted by
BootSlick55
Obscure but good, eh?
Try the Gus Van Sant trilogy:
Elephant (this one especially)
Gerry
Last Days (not so good)
or
Dead Man
(by Jim Jarmusch starring Johnny Depp)
or
Donnie Darko.
Owning Mahowney (with Philip Seymour Hoffman) is also unknown but good. As is Love Lisa with the same actor.
It is the golden age of documentaries, so:
Crumb
Bus 174
Murderball
Born Into Brothels
Crazy Love (this one is a must-see)
Touching the Void (this one is probably well-known)