Dirty Dancing: Only film I ever saw at a drive in, still a personal favorite, I grew up going to Jewish resorts like the one in the film, oh and Jen Grey's mom in the film is the gramma from Gilmore Girls, which I love.
To Wong Foo: A personal fave of mine too. A bold choice on his part.
Donnie Darko: Few recall he was in it. A disturbing cult classic.
Point Break: Kinda silly but first time I heard the words "bodhi" and "Bodhisattva" (which I discussed in Religion in Anime & Manga" panel.