Because I was watching Dylan Baker in a Kings episode from last night, and he's in one of these, and I felt like a listy...
Notorious (1946)
I watched this film one day while cat-sitting at a friend's house. Alfred Hitchcock, Ingrid Bergman, and Cary fucking Grant in a familiar romantic AU fanfic plot done to perfection. I fell madly in love with Cary Grant after this movie. MADLY. I think it was filmed after his 2nd divorce, when he was in love with his stepson and newly over his 12-year affair with Randolph Scott. He's never looked better. And yes, that's saying a lot.
Happiness (1998)
Dylan Baker plays a pedephile in this Todd Solondz movie. I've probably seen it more than any other movie because I wanted to show it to everyone I know. It's that good. Funniest. Relationship. Movie. Ever. And possibly one of the reasons I'm a total commitment-phobe. CLASSIC.
Taxi Driver (1976)
I watched this one every day for one month when I lived in Philadelphia.
Apocalypse Now Redux (1979)
This one too.
Mulholland Drive (2001)
And Twin Peaks and Lost Highway and every little David Lynch thing.
Barton Fink (1991)
This movie will kick your ass. If you are a writer, you MUST watch it. And watch the whole thing. The Coen brothers' best movie, IMO. Also, The Big Lebowski, Miller's Crossing. Coen brothers, yes.
The Thin Red Line (1998)
Terrence Malick does poetry on film.
Velvet Goldmine (1998)
But since hopefully everyone's already seen that one, go check out Breakfast on Pluto (2005) because it has Cillian Murphy in drag and Liam Neeson as a priest and who doesn't love that. Also, it's Neil Jordan. Oh, also Sunshine (2007) is great.
The Graduate (1967)
Plastics.
Reservoir Dogs (1992)
Possibly the slashiest movie ever, in retrospect.
And two crazy ones...
Superman Returns (2006)
My biggest guilty pleasure. My sister won me a blow-up Superman doll at the fair that summer because I was so in love with Brandon Routh. And I think I'm the only person who loved this movie.
Tras el Cristal (1987)
Marisa Paredes in an Augustin Villaronga film. (Oh crap, there's no Almodovar on this list... or Woody Allen... or Ingmar Bergman. Ok, um, All About My Mother, Annie Hall, and Hour of the Wolf?) About as Spanish and Gothic as you can get - the filming location was haunted, the mysterious star went blind. It's impossible to find info on this film. And it gets creepy if you do. Possibly the darkest movie on my list - a boy returns to reunite with his Nazi doctor torturer in something out of crazy dark!fic plot. Gorgeous like a dream. But, WARNINGS GALORE.