What was your gateway movie? The thing that made you say "oh, movies don't have to be what I thought they were?" For pre-color movies it was The Great Dictator for me, for a movie with a sad ending it was Being John Malkovich, for surrealism it was Eraserhead.
I know I'd probably love Eraserhead even more now but as a kid in high school in Kentucky it was just a jarring wtf. And I mean it when I say Being John Malkovich was the first time I realized I didn't have to feel happy at the end of a movie.