[diebitter]

Hmm, this is pretty personal and specific, I'm betting. Films that improve with viewing (or at least seemed better the second time than the first) for me were:

Young Frankenstein (which I enjoyed as silly the first time, but now think is actually pretty masterfully made)

Equilibrium (went from downright hated the first viewing, to pretty okay the second time)

Empire Strikes Back (liked it obviously the first time, but thought ep 4 was way better, but, meh, you live and learn)

Ed Wood, Sleepy Hollow (I've noticed it's often the way with Tim Burton films that they improve with more viewings)

Mallrats