Oh, I just remembered another I watch repeatedly. I love Tombstone (Kurt Russell and Val KIlmer). There's one line in that movie that my husband uses to describe me when I get really ticked off about something --'You tell 'em I'm comin', and hell's comin' with me!" Strangely enough, if you find a picture of Wyatt Earp he & Kurt Russell look a whole lot alike
The Shawshank Redemption
Meet the Parents
One Flew Over the Cuckoo's Nest
The Big Lebowski (gets better with every watch!)
Dirty Dancing
Gone With the Wind
Happy Gilmore
So I Married an Axe Murderer
Zoolander
When I was a teenager, my best friend and I watched 'Aliens' every time he came over. I think we watched it ~40 times that summer and could pretty much recite the whole thing.
I've watched the original Star Wars trilogy dozens of times (like Coolcat, not the 'improved' versions they're showing now.)
I watched Star Trek II and IV a bunch (there's that weird even-odd thing with them).
I probably watched A Knight's Tale 10 times back when I had HBO.
More recently, I've watched Serenity 4-5 times, and Office Space probably 6-8.
I tend to be weird with repeating movies. I'll have the DVD sitting on my shelf and have no interest in watching it, but it will come on cable and I'll sit through the whole thing (commercials and all).