Undercover Blues. I could list others, but they’re all on other people’s lists. This is my little rewatchable gem.
Oops, wrong thread.
Here to mention The Blues Brothers.
I second “The Man Who Would Be King.” Another great soundtrack 
The ones that I get out at least once a year:
**Reality Bites **[months go by and then I think, it’s time for Reality Bites again]
**Love Actually **[at Christmas]
Something New [months go by and then I think, it’s time for Something New again]
The one I’ll watch any time I can rope someone new into experiencing it:
Gallipoli
The ones that I watch whenever they come on TV, and I get roped in:
Sweet Home Alabama
How to Lose a Guy in 10 Days
Pretty Woman
**Blues Brothers
Mean Girls
My Neighbor Totoro
Shaun of the dead
Anchorman**
Strange collection of movies. True though.
I should also put down some others that I watch a lot that I don’t actually like that much:
Against All Odds
Sphere
I’ve gotten into the habit of studying in front of the TV set, and I need something to serve as white noise in the background to concentrate. Against All Odds and Sphere are fairly brainless thrillers that don’t engage me that much, and I managed to get them dirt cheap, so when I have a lot to get through, I plug them into the DVD player and just concentrate on what I’m studying. When one’s over, I take a study break, and then I just plug the other one in.
Of course, I don’t really wind up watching them that much, so these might not count.
Shakespeare in Love.
Most of the movies I watch over and over again have bad, suggestive puns for titles. 
You mean you just keep putting them in and out, in and out of the VCR/DVD player?
It’s A Wonderful Life
A Christmas Story
Forrest Gump
Platoon
We Were Soldiers
Hamburger Hill
Star Wars Original trilogy
Rear Window
North By Northwest
To Catch a Thief
Psycho
and, to get away from Hitchcock,
Anatomy of a Murder
The Manchurian Candidate (do you even have to ask which?)
Bell, Book, and Candle
and, of course
The Princess Bride.
Pride and Prejudice the Colin Firth version and the Keira Knightley version, I have watched probably around 75 times. It is a very good movie to knit too.
Ocean’s 11 and 13 12 was crap. Another very good listening too film. At least 50 times. Each.
Snatch. Pulls me in every time. at least 5 times a year.
**Harry Potter ** all of them. I get in a mood and just watch them in order. Can’t wait for 6. Lost count of how often I’ve watched them.
One hand on the fast-forward button and one hand…
If I come across any of the following movies while channel surfing, I am obliged to watch them to the end:
**The Blues Brothers
The Fifth Element
Airplane
Cars (if my son is watching too - he’s crazy for it too)
Jaws (but only until the Kitner kid gets it 22 minutes in)
Aliens**
Armageddon - I’ll always stop to watch that one.
Die Hard - Yippie Kay-Yay!
Terminator - Love the original.
Princess Bride - The motherload of geek quotes.
And almost any episode of Phineas and Ferb.
Pretty in Pink
Bride & Prejudice
Pride & Prejudice (the Colin Firth version)
Grosse Pointe Blank
Shrek
Back to the Future trilogy
Original Star Wars trilogy
Let us know what ya think.
Yup.
Jaws
Star Wars (and that includes the awful newer ones, that we watch marvelling at the awfullness)
The Matrix
Excalibur
Merlin (mini-series with Sam Neill)
Edward Scissorhands
What’s Eating Gilbert Grape
Chicago (for the musical numbers)
All Harry Potters
All LotR
A Christmas Story
The last three I would, if left to my own devices, sit and watch from beginning to end, and A Christmas Story I would sit and watch for all 24 hours.
Ben Hur
King of Kings
The Ten Commandments
…and…when babysitting, I bring along Homeward Bound (the newer one) to keep the kiddies entertained, and I end up crying for happiness at the end, every single time.
Oh, and Beauty and the Beast, the black and white French one with sub-titles.