The entire Saw series! I don't care what the haters say or think, I love these flicks and continue to watch them all over and over.
I think Frailty might be the best movie to come out since 2000. Not sure how many watches it has total, 3 since I started keeping track in 2004.
Cabin in the Woods will be there, watched twice and I've only owned it a month! Plus it was just as good on second viewing even knowing what was coming!
Innkeepers did not hold up well to a second viewing in a month for comparison.
Jason X! 5 times since 2006, at least 4 before that. It might be my favorite Friday just for replay value and good silly fun.