Life is too short on wasting your valuable time watching a movie again and again.
I have made a point of trying to find movies that I want to watch multiple times, even many times. But I have never gotten the bug like a lot of people. There's no movie that I've watched more than a dozen times.
Jerry Maguire I've watched 12 times. Partly because a certain person I met online said she watched it at least once a month. The next most times I've seen a film is 8 times, Casablanca. Saw Jurassic Park and Pulp Fiction 6 times. About 8 movies 5 times. I keep this info in a data table with other info.
Some movies really do work well in mulitiple watches, even close together. I forget a movie, many I can watch a few years later and not remember what happens and it works for me again. But I don't rewatch as much as many people do, favorite movies. Many movies just suck the first time. Occasionally I'll rewatch it later thinking maybe I was in the wrong frame of mind the first time, but usually I still dislike it... not always!
These are the movies I've seen more than 3 times, in descending order, the most at the top:
Jerry Maguire (Cameron Crowe, 1996)
Casablanca (1942, Bogart)
Pulp Fiction (Tarantino, 1994)
Jurassic Park (Steven Spielberg, 1993)
L. A. Confidential (1997)
Titanic (James Cameron, 1997)
It's a Wonderful Life (1946)
Unforgiven (1992, Clint Eastwood)
Fargo (Coen Brothers, 1996)
Office Space (Mike Judge, 1999)
The Godfather (Coppola, 1972)
Robocop (Paul Verhoven, 1987)
The Matador (2005)
Lawrence of Arabia (David Lean, 1962)
When Harry Met Sally (Nora Ephram with Rob Reiner, 1989)
Groundhog Day (1993)
Easy Rider (1969)
The Big Lebowski (Coen Brothers, 1998)
Eternal Sunshine of the Spotless Mind (Kaufman, 2004)
Nashville (Robert Altman, 1975)
Airplane! (1980)
Ghost World (Terry Zwigoff, 2001)
Indiana Jones and the Raiders of the Lost Ark (Spielberg, 1981)
The Terminator (Cameron, 1984)
The Departed (Scorsese, 2006)
Apocalypse Now (Coppola, 1979)
Juno (2007)
The Pink Panther - A Shot in the Dark (1964) (in Collection) Not for a long while!