The Hills Have Eyes remake - 7 times
LOTR: The Fellowship of the Ring - 5 times
LOTR: The Two Towers - 2 times
LOTR: The Return of the King - 2 times
The Hills Have Eyes original - 2 times
I Spit on Your Grave - 8 times
28 Days Later - 6 times
Mercy Streets - 3 times
There are many more, and some movies I've seen so many times I can't count them.
The Parent Trap(the one with Lindsay Lohan), from the time I was about seven to the time I was twelve, I watched this movie almost EVERY NIGHT. We had recorded it on to a Video, and by the time I was twelve, I couldn't watch it any more because it had developed so many lines and the dialouge was off.
Sister Act, Sister Act 2, Father of the Bride, Father of the Bride 2, Cheaper by the Dozen, Cheaper by the Dozen 2, When Harry Met Sally, You've got Mail, Sleepless in Seattle, Grease, Grease 2.... I can watch just about all of these any time...