Check out The Forbidden Room (it's on Netflix). I don't know about this "strangest of all time" business, that's a tall order, but it definitely deserves a mention in the conversation. Also, it's pretty great.
shareDog Tooth is up there for sure.
shareGummo, probably
shareBrazil was strange and pretty entertaing...
shareZardoz was another weirdo one
Man...James F'ing Bond in hooker boots and a red 'mankini as the last gun toting/female screwer in the universe...not joking, thats what it was about...pretty goddam oddball stuff...and great!
Mine isn't the strangest , but it's differently weird. Rubin and Ed.
share"Enemy" ... Not strangest, but strange enough... Worth checking out
share