Dr. Caligari (1989)

If the makers of the original 1919 silent German classic (which I'm also a fan of) knew about this long belated sequel, they'd be rolling in their graves. 70 years later, Dr. Caligari's lusty granddaughter has apparently gotten her medical license, and she upholds the family tradition by bending over backwards to make the patients in the asylum she runs feel even more insane. With its low-budget, '80s music video look, porn-quality actors and non-plot, this grotesquely perverse and surreal film feels like an overlong, bad dream. May possibly top the list of the weirdest movies I've ever seen... and by my reckoning, that's a huge compliment.