GRcade

Alien. And then T2, The Matrix and Aliens.

Die Hard is by far the most. I couldn't tell you how many times, must be more than 30. I watch it at least once a year, sometimes 2 or 3 times.

Also, glancing at my old DVD collection..

Commando
Predator
The Terminator
Alien
Aliens
Speed
Leon
The Rock
The Thing
Robocop
Jurassic Park
Pulp Fiction
Reservoir Dogs
Dumb & Dumber
The Big Lebowski
Fargo
Back To The Future
Raiders of the Lost Ark
The Last Crusade
Die Hard With A Vengeance
The Matrix
From Dusk Til Dawn
Titanic
Seven
Heat
are the ones I've seen about 10 times each or more.

Mine are likely Jay and Silent Bob Strike Back, South Park: Bigger, Longer and Uncut, the original Star Wars trilogy and Evil Dead 2.

It's quite sad to admit now but at one point I knew most of the script to the South Park movie

Transformers the Movie (1986)
Back to the Future Trilogy
LOTR Trilogy
Hot Fuzz
Terminator 2
Alien and Aliens
Rocky 1

No Escape (the 1994 film, not the new one).

It was the first VHS movie I owned, and I strawberry floating loved it. It's got Ray Liotta and Lance Henriksen in it, and has pretty much everything a 15 year old kid would love in a movie. I must have watched it like fifty times. Haven't seen it in years, but it's probably awful.

These days I don't tend to rewatch movies that often, Die Hard or Star Wars probably have about four or five views each I guess.

EDIT - I tell a lie, I've seen Cars (the Pixar movie) at least 20 times thanks to my lad.

Die Hard
Aliens
Terminator 2
Commando
Predator

Easily watched all of those at least 20 times each. Best films eva IDEMT xx

Actually, my top 2 and 3 may need to change, I've seen the original The Evil Dead at least 3 times.