The Marx Brothers movies. Obviously. 
All numbers are rough but fairly accurate guesses.
Jeremiah Johnson - 20, it’s who I’d like to have been 150 years ago.
Fandango - 25, hilarious, quotable, know the writer/director, hits home.
Holy Grail - 30, what’s to explain? Funniest movie of all time.
Dr. Strangelove - 15, smart, perceptive, amusing.
Bullitt - 15, the chase scene… probably closer to 40.
The Thing - 12, everytime there’s something new to wonder about. How were Carpenter’s other movies so bad and this so good?
Reservoir Dogs - 12, Simply badass.
King Kong (the 1933 version, of course)
**Forbidden Planet
2001 ** The two best science fiction movies made.
**A Man for All Seasons
Spartacus
The Seven Samurai ** My favorite historical dramas
**The Seventh Voyage of Sinbad
Star Wars
The Empire Strikes Back
Return of the Jedi
The Day the Earth Stood Still
The Day of the Jackal** – my all-time favorite thriller
The Guns of Navarone – you can’t sleep through it.
… a couple more to add.
To Live And Die In L.A. - 10, first movie to see either Petersen or Dafoe in, a fan of both ever since.
Predator - 12, perfect movie to demo home theater with.
I’ve no idea how many times I’ve seen bits of all the spaghetti westerns, Joe Kidd, Pale Rider, etc. (dozens) but, strangely, rarely ever saw one start to finish.
Disney’s The Little Mermaid. Why? Cuz I love it.
I was one of those geekazoids who saw the original Star Wars in the theater over 100 times. I just couldn’t get enough. That was back in the days before VCRs and I just had to see it over and over because I thought it would go away and I might never see it again when I wanted. Who knew when they were going to play it on TV, and then only once. My son was a big fan too, but he became a fan because I took him so often. I was the obsessed one.
For a more recent obsession, I saw The Matrix in the theater over 30 times. I lost count. Strangely, we’ve owned the DVD since the day it was released and I haven’t watched it once, but if I see a revival of it playing anywhere, I’ll be first in line. There’s just something about seeing it on the big screen that I dearly love.
I saw The Fellowship of the Ring at least 12 times in the theater. More if you count several theatrical viewings of the Extended edition.
There are many dozens of movies I’ve seen more than 10 times, including
**Brazil
The Cotton Club
The Godfather
A Clockwork Orange
Moulin Rouge ** (another theater experience, because I’ve only seen it a couple of times at home)
Local Hero
Raising Arizona
Oh Brother, Where Art Thou?
The Big Lebowski
The Princess Bride
Never Cry Wolf
Life of Brian (my favorite comedy)
Real Genius
Galaxy Quest
Too many more to think of at the moment
I love some of your choices. There are so many little gems that I’ve seen several times too, like
I also love seeing movies like Elizabeth and House of Games on your list tdn! I’ve only seen them once each and it’s good to know they survive multiple viewings.
Yellow Submarine Brilliant animation, sight gags, silly humor, and the music. A certain, uh, state of mind unlocks this one.
My Favorite Year I just love it.
Raiders of the Lost Ark Perhaps the perfect action flick.
Bullitt The brooding McQueen, and the best chase ever. Anytime I can catch the last part on TV, I do.
Young Frankenstein I tried to read the book Frankenstein, but it depressed me terribly; I empathized with the monster. When I saw YF, I wept and laughed. Then I could go back to the book. The movie is simply perfect.
Other great Mel Brooks works: Blazing Saddles, The Producers, The Twelve Chairs.
The Holy Grail I don’t need to explain.
The following are movies I have seen too many times to count:
Raising Arizona
Moonstruck
Brokedown Palace
Star Wars (Episodes 4, 5, and 6, hereafter referred to as “The Ones That Count”)
The Breakfast Club
Disney’s Cinderella, The Little Mermaid, and Sleeping Beauty
What About Bob?
Why I like the movies I listed in my previous post posted here because I failed to read the OP in its entirety:
Raising Arizona- because it’s funny
Moonstruck- because of Olympia Dukakis
Brokedown Palace- because it’s the only movie that makes me cry every single time I see it
Star Wars (the ones that count)- no reason necessary
The Breakfast Club- it’s the first movie I memorized and drove my mother nuts reciting it all the time
Disney’s Cinderella, The Little Mermaid, and Sleeping Beauty- they are beautifully made
What About Bob?- because it’s funny
Last year at Christmas, I saw “the Polar Express” 4 times.
I watch Indiana Jones over & over, as well as Labrynith.
I can’t even begin to think of how many times I’ve seen some films on TV/DVD/VHS, so I’m not going to list them. The list would include such titles as The Godfather, Moulin Rouge! (a particular favorite of my daughter and mine), Jaws, The Manchurian Candidate, and a host of others.
Then you get into the question of what really constitutes “watching” a movie - does catching the last half of Jaws while channel surfing count? If you fast forward through the sequence where Nicole Kidman is writhing on the floor (or the Roxanne tango) in Moulin Rouge! 'cause it’s something that your three year-old doesn’t need to see, did you really “watch” it?
Regardless, when it comes to paying to see movies in the theater my easy #1 is Titanic, which got me in the doors no less than 6 times during its first run and a couple more when it finally hit the dollar theaters. I love big, sappy epic romances (to which I am just THRILLED that the 3-4 disc SE is finally coming out this September (or October), replacing the crappy 1 disk job they released back in '99, 2000.) I am so there! 
#2 is the recent War of the Worlds which I’ve already seen 4 times. I think I saw ET another 4 times in the theater as well.
Big Lebowski for sure. I’ve probably watched that over 20 times.
I watch Night of the Hunter a lot. It’s my favourite.
Bridget Jones’s Diary. That’s a bit embarassing and spinsterish of me but it hits the spot when you’re feeling blotchy, drunk and alone.
Stuart Saves His Family. That’s good for when you’re feeling sober, blotchy, and alone and you know you have to see your family in a few hours and they’re going to be mean to you.
Elf. That’s good for when you feel alone in your love of Will Ferrell.
My top five would be:
The Princess Bride
Blazing Saddles
The Breakfast Club
Pulp Fiction
Groundhog Day
I have know idea which is the winner, I’ve seen them all at least 20 times.
In the “at least ten times” chategory:
Star Wars
The Money Pit
Plains, Trains & Automobiles
The Never Ending Story
Iron Giant
The Ref
The Long Kiss Goodnight
Indepence Day
Airplane! This one probably should have been in the over 20.
Raising Arizona
Die Hard Cone to think of it, this one is probably an over 20 too.
The Matrix Also a probable over 20.
The War of the Roses Because I find Kathleen Turner’s voice hot!
Looking at my list, I’ve watched three of those in the last week. Five in the last two.
What movies have you heard the most times?
With a little girl in the house, I’m sure I’ve heard Pocohantas and The Lion King dozens of times. And we’ll not even go into that bizarre fascination with Baby Einstein: Mozart, which had her watch the same tape 15 times in a row (not at the same time, but for a 3, 4 day period that was ALL she wanted to watch.)
Many parents here can likely say the same about these and other films. 
- Star Wars - Because I’m a geek.
- The Usual Suspects - Love the film, but have also written several (unpublished, unlikely to be published) papers on it.
- Tron - I’m not really sure why.
**Ghostbusters
Airplane
Phantom of the Paradise
Rocky Horror Picture Show
Star Trek ** (all of them)
**The Wizard of Oz
Finding Nemo ** (mine! mineminemine!! mine!!! mine!mine!mine!)
Beetlejuice
Don’t know if this counts, but:
Pink Floyd Live at the Berlin Wall
I’ve probably seen Back to the Future near 100 times. If not more.
My brother and sister and I, who all had (and still have) very different tastes in movies (Him: Schwarzenegger, Me: P.T. Anderson, Her: anything mainstream and big-budget), were all obsessed with the story of Marty and the Doc. Since it was the one movie we all agreed on and loved, it was on constantly. We had a separate copy of the film in our van, which had a VCR. We knew all the little trivia in addition to the complete script, which we could recite together while playing different characters.
It became a sort of comfort food, and when I went off to college, I’d put the VHS tape in whenever I was feeling blue. Two years ago, our parents bought each of us the DVD set of the BTTF trilogy, with all the commentary. We had watched II and III somewhat, but not nearly as much as the original–which is still my favorite all-time movie.
No other repeat viewings of mine can even compare. I’m a big dork. :o
The Rocky Horror Picture Show - at least 100 times , I stopped counting . I often saw it twice a week at midnight showings when it was still playing , and now watch it on video on occasion for ‘old time’s sake’ .
A Knight’s Tale - It is my pick-me-up-feel-good movie . I have seen it so many times I can quote the dialog right along with the movie . (Besides , Heath Ledger looks HOT in it . Yeah , yeah , yeah … I’m old enough to be his mama . And if that makes me a dirty old woman , so be it 
)
All 3 LOTRs - gotta love them !
Wayne’s World
I’m not quite sure why, as I don’t really identify with either Wayne or Garth, but the humor in that movie TOTALLY struck a chord with me. I saw it 7 (I believe) times in the theaters, then bought the VHS tape the day it was released, watched it over and over again until the tape actually wore out, bought another tape, and then bought it on DVD the day it was released. All in all, easily 100+ viewings.
Diggstown
Noises Off!
Mystery Science Theater 3000, The Movie
High Strung
The Shawshank Redemption
Down Periscope
Dirty Rotten Scoundrels
The first two are definitely faves, but I never seem to get tired of any of them.
On the list of “heard/seen it thousands of times because the kids love it,” the number one spot has to go to Three Men and a Baby. I truly enjoyed the movie the first time I saw it. But when my daughter was about 2 years old, she decided it was her favorite movie and watched it incessantly. I grew to hate it, and only now, about 8 years later can I stand to watch it!