Besides the usual movies like A Christmas Carol and other holiday themed films. I would have to say The Shawshank Redemption...I watched it 4 times before I actually read the Stephen King novella, which the movie stayed true to almost every sentence. Jaws probably comes a close second.
I know a lot of people rewatch that but IMO it bites.
For me, most watches at the top, all at least 5 viewings:
Jerry Maguire
Casablanca
Jurassic Park
Pulp Fiction
The Matador
Robocop
The Godfather
Titanic
It's a Wonderful Life
Unforgiven
Office Space
Fargo
L.A. Confidential
Most likely Office Space. I think I've watched it at least 30 or 40 times.
I bought it twice, 2nd time to get a better edition. Yeah, one of the greatest. Just brilliant. The beginning of that movie is perfect, the scene on the freeway.
How do you remember, up to 153, how many times you have watched a movie?
Myself, when I watch a movie I enter that watch into my movies database... also the date, long as I remember to. I blow hot and cold. Sometimes I watch a few movies a week, but I can go weeks without watching any movies.