Good topic. I can't stand to watch movies more than once generally.
A few good ones, I can watch again much later.
Off the top of my head, pretty much picking from the posts above:
Dr. Strangelove (a few times, very rare)
Platoon x2
Lord of the Rings several times because of commentary tracks
2001 a few times
Alien a couple times
Blade runner x2
Just watched Big Trouble in Little China a second time.
The Corporation twice.
James Bind movies once every so often.
I could watch some more again, Hitchcock classice like North by Northwest, Seven Samurai, Roshomon. The Koyanisqaatsi series.
Hard to think of one I'd watch a second time soon after seeing it.