Well, I guess I’ll put Stranger Than Fiction in the queue.
I always end up watching at least part of Beetlejuice, The Princess Bride, Swingers, Office Space, Stand By Me and Clueless when they’re on TV. Or at least every fourth or fifth time. So every month or so.
Blood Simple
Good Will Hunting. About twice a year.
I don’t think I could stand doing that with any other movie, but Will Hunting? Can’t get tired of it.
Cyrano de Bergerac, the 1990 version with Depardieu.
The Court Jester, a wonderful Danny Kaye romp. “The pellet with the poison’s in the vessel with the pestle…”
OMG, nobody’s mentioned The Princess Bride yet???
I was elated to discover just yesterday that it recently became available on Blu-Ray; upgrading to HDTV shortly, and this will be one of a very very few movies I will buy on Blu-Ray.
Jaws
Aliens
Alien
The Abyss
The Matrix
Glengarry Glen Ross
The Hunt For Red October
Caddyshack
My Cousin Vinny
The Blues Brothers
**Forbidden Planet
Spartacus
The Seven Samurai
Day of the Jackal
Star Wars
The Empire Strikes Back
Return of the Jedi
The Day the Earth Stood Still
Metropolis** (The Giorgio Moroder version)
**The Seventh Voyage of Sinbad
On Her Majesty’s Secret Service
The Matrix
Fantasia
Fantasia 2000
MST3K the Movie**
I feel the same about Rounders…I’m not entirely sure why I have to watch it whenever it’s on. I mean, I’m not really into poker and while the acting is great, it’s not something that would draw me in time after time.
Grosse Point Blank and the Blues Brothers. I can watch them over and over again. Not even my favorite movies, but they just don’t get boring.
The Man Who Would Be King is the big standout. I watch it easily 5-6 times a year. My son insists on watching The Spongebob Squarepants Movie at least once a month.
I’ve lost count of the number of times I’ve seen The Third Man, but it’s several dozen. I’ve seen it more than any other movie, and continue to watch it 2 or 3 times a year.
Trainspotting*- about 5 times a year since it first came out on VHS 
Lonesome Dove- at least twice a year
Rounders- whenever it’s on TV
Office Space- Ditto
Most of the Jane Austen type flicks- especially:
Sense & Sensibility (Emma Thompson version)
*Persuasion *(BBC version with Amanda Root).
Pride & Prejudice (BBC version with hot Colin Firth scene)
Seen these way too many times and still watch
Aliens
Mystery Men
Anything starring Barbara Harris
I’ve pretty much used these up
Real Genius
Repo Man
The Incredibles
Forbibben Planet
Nashville
Blade Runner
Casablanca
My Man Godfrey
They Were Expendable
Thirty Seconds Over Tokyo
The Duelists
Crossroads (the Ry Cooder one, please)
Galaxy Quest
The Incredibles
Last of the Mohicans
North by Northwest
Any of the Monty Python movies
This Is Spinal Tap
The Blues Brothers
Office Space
Airplane! (best watched with my brother and his friend, who can recite every line)
Trainspotting
Ferris Beuler’s Day Off
Rocky
Clueless
Legally Blonde
The Godfather I & II
Apocalypse Now
Blazing Saddles.
The Princess Bride.
The Usual Suspects.
Something I just not realized in this thread…
There are a crapload of people who simply adore Stranger Than Fiction. I seriously thought I was the only one who liked this movie as much as I do. I know others who have seen it, but I never knew so many people liked the thing as much as I.
*It’s a Wonderful Life *- Is that one so obvious that nobody felt the need to list it?
The Princess Bride. - The second most perfect example.
Stranger Than Fiction. I really don’t know why because I could do without Will Ferrell. That movie just works somehow.
Aliens
Zulu
So many more, a lot of them list by others. There are a lot of movies I never think aobut until I walk into the room and they are on TV. I can sit down in the middle and just go from there.
Bad Santa