Movies I've seen a lot and still watch fairly regularly:
Miller's Crossing, Batman Returns, Donnie Darko, Unforgiven, Yankee Doodle Dandy. ("One of these things is not like the others...")
Movies I've probably seen as many times, but not in the past decade:
Back to the Future, Aliens, original flavor Star Wars, Bladerunner, Heathers, Raiders of the Lost Ark.
Runners-up:
Tapeheads, Casablanca, Star Trek 2, Buckaroo Bonzai, A Fish Called Wanda, The Private Life of Sherlock Holmes, Shadow of a Doubt.
It occurs to me that I've seen
The Secret of My Success
an unholy amount of times.
I've watched The Haunting (the Wise version), The Day The Earth Stood Still, and Nosferatu quite a number of times, too.
Now that it's been more than ten years, can I expunge the near-daily viewings of Encino Man from my record?
Someone needs to check the rule book for Jesse.
I think I saw Ferris Bueller five or six times the week it came out. We were on half days at school that week for exams.
Others -
Blues Brothers
Rosencrantz & Guildenstern
Henry V (Branagh)
Top Gun, ugh. (That was on pretty much constant replay at my house for a whole summer. Not by me.)
Romeo + Juliet
Three Kings
Strange Brew
Friday
Branagh's Henry V is something I love to pop into the DVD player when I start cleaning the apartment. I can just recite along with some of those speeches while dusting/doing dishes!
Rosencrantz & Guildenstern
Oh yeah! That!
Heh. I was just thinking I needed to add that to the shelf of comfort movies.
Also, Velvet Goldmine.
That's
already
on the shelf of comfort movies.
The movie I've most watched in the theater is probably
Grease,
which I saw 5 times when it first came out (between friends and babysitting and the fact that we only had one local theater). Although
Willy Wonka
played there every year for awhile so that might be a close second.
Movies I've watched most on TV/DVD:
Caddyshack, Chitty Chitty Bang Bang, Dirty Rotten Scoundrels, The Thin Man, Heathers, High Society, Monty Python and the Holy Grail, Sound of Music, Wizard of Oz.
Growing up before VCRs, I really racked up viewings of things that showed ritually on TV every year.