Personally, The Rocky Horror Picture Show.
I knew it was going to be quite the experience before I went for the first time‡ but it was so much fun I had to keep going back bringing friends each time.
It’s still a fun tradition to do though we haven’t done it since last year, we’re probably going to try and go again in a few weeks.
‡ I had seen it many times before going to see it in theaters for the first time.
Titanic. Saw it 4 times in the theater.
I actually wondered if it was going to sink the first time I watched it. Movie is so well made you didn’t even realize what’s going to happen until it does.