I saw the Iron Giant like 4 times in the theater. Grown man here, too. What can I say? The movie really struck a chord in me. Hadn’t felt that giddy about a movie since I was 7 and went to see Star Wars, some… 24 years ago. (yeeesh!)
I also saw Jurassic Park about 3 times, same reasoning as above, though I’m still more of an Iron Giant fanatic. I think of JP as being more of an “event movie”. Something you gotta see on the big screen.
Other notables: So I Married an Axe Murderer and Galaxy Quest.
Twice each. If only because I had to drag other people to see it, who didn’t believe me when I told them how good they were.
I’ve only seen four movies twice in a theater, but in all four cases it wasn’t because I was in love with the movie (I only REALLY liked one of them), but because I saw it with someone else the second time.
E.T. - caught it on it’s first run, and then in a drive-in with my nephew and niece a year or so later.
The 5th Element - I thought it was dumb when I saw it the first time (by myself), but my girlfriend really wanted to see it so I saw it again with her.
Starship Troopers - I loved the movie, but didn’t need to see it again - but I knew someone who thought she would hate it that I knew would love it, so I took her to see it (and I was right). Unfortunately, I had to agree to watch a movie of her picking to get her to go, and had to suffer through Selena.
Blade - saw it twice with the same person, the first time when it first came out, the second time as a part of a Halloween triple-feature.
There are some movies I have watched a great number of times on cable or video.
Sgt. Pepper’s Lonely Hearts Club Band - I figure I have watched this movie at least 60 times. When I was a child it was in heavy rotation on HBO, and I watched it every chance I got. The only reason I can think of now is my childhood obsession with George Burns. I watched it again recently for the first time in about 18 years and I can’t think of any other reason why I might like it.
Animal House - Another film I watched every chance I got on HBO. I probably saw it about 30 times before I was 10 (I’d see it more but I had to be sneaky about it because of the nudity).
Pink Floyd’s The Wall - This was the only videotape my roommate owned back when I lived in a trailer house outside of town. The TV was used for playing Super Nintendo and watching The Wall, we didn’t get any channels and couldn’t afford to rent anything. I probably saw it about 50 times.
Evil Dead 2 - I probably watched this about 20 times at least. Didn’t own it, just rented it a LOT. Great movie, but I watched it again recently and I can’t see why I would watch it 3 times in one night - but then, I didn’t have any weed the last time I rented it.
Honorable mention goes to ‘Twilight of the Cockroaches’, which I have rented about 5 times and have maybe watched 7 or 8.
I saw Toy Story four times – first time by myself, second time with friends, third time escorting my mother, fourth time with both my parents (Mom insisted on dragging Dad along).
Saw Titanic twice (bleagh :P), first time with my wife, and second time escorting Mom again.
And most recently, I saw Crouching Tiger, Hidden Dragon twice. But that was only because the first time my wife got ill twenty minutes before the end, and we wanted to see how it finished…
All in the theaters, of course. At home, I’ll watch any ol’ thing any number of times.