This article on high-school films is interesting, although I haven't seen some of them (especially Donnie Darko, which I must get out on video one of these days). I notice "The Virgin Suicides" got an honourable mention. It's true - it's not a terribly good film, but the book is much much better. You should read it if you haven't already. I read it in one big gulp on a long train journey last year, and I barely noticed I'd been sitting in one position for about 3 hours.