The Fist of Legend - 30+ times
Kung Fu Hustle - 20+ times
Transformers - 20+ times
Tommy Boy - 20+ times

each of lord of the rings six times.

terminator 2 40+ times
Day of the Dead 40+ times
Land of the Dead 30+ times
Shaun of the Dead 30+ times
The Last Man on Earth 20+ times

Of all time?

Probably, Harold and Kumar: Escape from Guantanamo Bay.

Also see Titanic, Shrek 2, Nightmare on Elm Street, Child's Play, Carrie, Pokémon: The First Movie, James and the Giant Peach, First Blood, Dead Presidents, Tommy Boy, Black Sheep, The Nightmare Before Christmas, Jack Frost, Big Daddy, Heartbreak Kid and Forrest Gump

EDIT: Forgot a few, Taken, The Little Mermaid, Bad Boys, Cabin by the Lake, The Simpsons Movie, Final Destination 3 and Zoolander.

The Princes Bride and Gladiator

Movies I've watched a lot of (not in order):

1. Adam Sandler's Eight Crazy Nights - Probably 10 times

2. Pirates of the Caribbean - At least 5-6 times

3. Star Wars original trilogy - 5+ times

4. I've watched each bond movie at least twice. The good ones like Goldeneye/Tomorrow Never dies probably at leats 5 times each.

5. Billy Madison & Happy Gilmore - Probably close to 10 times each

Asspocalypto
Beaver and Buttface
Malcolm XXX
Rambone
Sasha Grey's Anatomy
Sex Trek: The Next Penetration
Sperminator
Star Whores
The 69th Sense
The Slutty Professor
Womb Raider

what.... those are movies too...

I watch Pixar movies loads of times. Also, Groundhog Day which I must have seen a dozen times.

I don't count the number of times I watch a movie but some good guesses are:

-Star Wars trilogies (a bajillion times) -Yes. Even the Prequels
-Memento
-Terminator 2
-Aladdin
-Finding Nemo (when you have kids, you'll see why)
-Metal Gear Solid 4
-The Color Purple

Couldn't possibly give you a number.

But I've watched some movies well over 100 times throughout my life.

I watch a lot of movies but in the cinema and at home.