Hedwig and The Angry Inch
Originally a cult performance in the meat-packing district in NY, this film is raw. Hedwig brings fascinating characters, great music, and surprising performances to the table.
I watched this film three times in a row after we bought it... got the soundtrack and watched all of the extras that same week. I got a few others to watch it too, but all seemed confused about my (at that time...) infatuation. There are these angsty animated illustrations that bridge Hedwig's love life, child hood and singing professional life together.
The extras on the dvd are pretty fresh as well.
It's not something to watch with others who are opposed with homosexuality, sex changes, cross-dressing, modern love tales, and rock-operas but who watches cool movies with people like that anyhow? Think Rocky-Horror Picture Show meets... I dunno, Say Anything?... I'm stretching there... watching this one with like-minded people.