Movies you watch over and over and over again.

Miller’s Crossing
Collateral
Snatch

Blade II. Works well for a background movie, and I love the first two films anyway.

D2: The Might Ducks (I saw it so much as a kid, and it just stuck with me)
Die Hard: With a Vengeance (I had hbo/cinemax when this would be played all the time and I watched it a lot)
Clueless (same as with Die Hard: With a Vengeance)
Hackers (Mess with the best, die like the rest)
Any Given Sunday (I watched the game scenes once a day for a long stretch when I was in college, but the rest of the movie is great too-- plus the ending is great)
Center Stage (Zoe Saldana’s first movie!! Plus it makes me think I actually understand ballet)
Josie and the Pussycats (almost a perfect movie)
Robin Hood (Disney version)

Sunset Boulevard

Seven Year Itch

Predator

Casablanca
Being There
Apocalypse Now
It’s a Wonderful Life
Groundhog Day
Citizen Kane
Saving Private Ryan
Various Buster Keaton films
Various Woody Allen films, but especially Annie Hall, The Front and Mighty Aphrodite

Based merely on rewatching and not on what’s my favorite per se:

A big me too on:

Stranger Than Fiction
Princess Bride
Gross Pointe Blank
Love Actually
The Fifth Element

Also:
Galaxy Quest is extremely rewatchable
Serenity
Star Trek First Contact
Star Trek (2009) - saw it three times in the theater so I suspect this will be making the list
Delicatessen
Hitchhikers Guide to the Galaxy
Creator
Electric Dreams
Dude Where’s My Car
Fried green Tomatoes
Moulin Rouge
Surf’s Up
Young Einstein

Just when I’m in the mood:
Beautiful Thing
Big Blue
Donnie Darko
Fight Club
Home at the End of the World
Color Purple
The Cell

Rocky
Rocky II
Silverado
The Untouchables
Unforgiven
Stripes
Field of Dreams
Roadhouse
Pulp Fiction

Ok, let’s put a small twist on this thread (and by “small twist” I mean "my actual intention).

Name just ONE movie that you watch over and over. As backround noise, cuz it’s your favorite, whatever one you watch the most and never ever get tired of it.

Mine is the afore (and aplenty) mentioned “Stranger Than Fiction”

I cannot have a movie as background noise, as I find I must devote my fullest attention to it always. We treat watching a movie at home like it was going to the cinema. Lights out, phones off. But if I did have one on much of the time, it would be Casablanca.

The Road Warrior. It’s laconic and brutally efficient, and I never tire of it.

Zoolander. Every time a new Will Ferrell or Ben Stiller movie comes out, I think “Is this it? Could this be the one that finally lives up to Zoolander’s eminent quotability, absurdity, and hilariousness?” Sadly, it never is.

*Willy Wonka and the Chocolate Factory *- loved it since I was a kid, can practically quote the whole thing now.

Jurassic Park. Just the first one, though.

Raiders of the Lost Ark

*The Manitou *- cheesy bad horror movie from the 70s, but I love it.

Harry Potter and the Sorcerer’s Stone

Dogma

Silence of the Lambs

The Sixth Sense

The Langoliers - Stephen King TV movie from the 80s.

Rocky Horror Picture Show

For background noise I either turn on the sci-fi channel or something random from my tivo, because that’s easier and lazier than popping in a DVD. I probably watch Serenity the most for just pure enjoying it as a favorite and a great film. Galaxy Quest and Star Trek First Contact are my more 'randomly filling up time with movies that aren’t super favorites but are extremely rewatchable" or for watching with friends.

As a kid, my most rewatched movies were the typical family films that were ‘events’ on network TV - Sound of Music, Wizard of Oz, and Chitty Chitty Bang Bang.

I can’t really do movies as background noise either. But the movies I watch over and over again are:

Barton Fink - I simply cannot get over how awesome the dialog in this movie is. “I’ll show you the life of the mind!!!”

Millers Crossing

Burn After Reading - I’ll stop with The Coen Brothers here, seeing as I could list almost all their movies.

Stranger than Fiction - I’m with Sir T-Cups on this one, I thought I was alone in liking this movie as much as I did. Also, I mentioned it to a girl I’m dating and she said she hated it. WTF? And she generally has good taste in movies.

Gross Pointe Blank

The Dark Knight

It suffers from the same problem The Truman Show did: a goofy comedic actor in a sometimes-amusing-but-overall-serious role. Folks expect a certain style from the actor, get thrown off, and get annoyed about it.

I really like the suggestions for ‘re-listenable movies’. I need aural stimulation at work to keep my productivity up, and I’ve taken to playing Netflix movies in the background. Their Watch Instantly list gets longer by the day, and they’ve gotten some great movies in there. I’m always looking for new suggestions of movies I’ve seen before (stuff that’s new is too tempting to watch; listening is fine, but watching kills productivity hard).

Session 9. There’s something about it that’s positively hypnotic to me.

I’ll stop what I’m doing and watch the following if I find it channel surfing:

Steel Magnolias
LotR: Return of the King
Fried Green Tomatoes
Dirty Dancing
Jaws
Forrest Gump
Mr. Holland’s Opus
Flashdance
Footloose
My Cousn Vinny
Se7en

and plenty of others…

Shaun of the Dead.

(You’ve got red on you…)

MeanJoe

Add to the above:

Being There
Fargo
Miller’s Crossing

If I was gonna mention a second movie…it would be “Hot Fuzz”