**1776
Singing in the Rain **
I’m going to try not to repeat any that others have listed, because there’s a lot of overlap.
The Bad Seed
What Ever Happened to Baby Jane?
The Mark of Zorro (the Tyrone Power version)
Muriel’s Wedding
Cabin Boy
Psycho
One Flew Over the Cuckoo’s Nest
Clueless
To Wong Foo, Thanks for Everything, Julie Newmar
A lot of picks already mentioned, so I’ll try not to do too much “Me too!” on my list.
My rewatchables:
John Carpenter’s The Thing - the tension, paranoia, etc, never gets old. I really like the 2011 prequel, too, warts and all.
The Big Lebowski - “Nihilists? Fuck me. I mean, say what you will about the tenets of National Socialism, Dude, at least it’s an ethos.” That line alone is worth the price of admission. John Goodman got robbed of a Best Supporting Actor award.
Raising Arizona - Hang on Junior, we’re going to get Daddy!
O Brother, Where Art Thou, No Country for Old Men, Burn Before Reading, Miller’s Crossing, True Grit, and Fargo (yah, you betcha!) all go on the list.
The Coens are just great film makers.
Buckaroo Banzai - crazy zany wacky fun every time I see it.
Alien & Aliens - Aliens especially can still elevate my pulse during the fight scenes.
Master and Commander: FSOTW - as a Patrick O’Brian fan, this movie is not only a spot-on perfect adaptation, it’s maybe one of the best “Wooden Ships/Iron Men” movies ever.
Open Range - I’m not a big Westerns fan, but this is one of my few; good plot (even if it is recycled), great dialogue, great chemistry, and a final showdown that’s epic.
That’s about all I can think of at the moment.
All good suggestions so far… a little light on the “why” so far, which is what I was most interested in (re-reading my OP yeah it looks like a throwaway comment). I agree with Namekcalb that movies with a good twist make good for repeat viewing (seems counter-intuitive since the twist is no longer a surprise) because you can look to see what clues are subtlety dropped early on.
So suppose I was a writer/director/producer (I’m not) and was making a movie and I decided for some reason that my main goal was to make a movie that people want to watch over and over again. What elements should I include? Or is it more of a je ne sais quoi property of the final product that can’t be planned?
Oh and,
Dances with Wolves
Eight Crazy Nights
As for the “reason(s) why,” they include great story, wonderful dialogue, and perfect casting. All of the movies I mentioned (and many more I can think of) were far greater than the sum of their parts, and therefore memorable.
Twister
Groundhog Day
National Lampoon Christmas
Most of the Marx Brothers movies
The Monty Python films
I’ll add:
Ronin
The American
The Professional
Blade Runner
Goodfellas
Heathers
The Cook, the Thief, His Wife, and Her Lover
and Bambi
Rope. The why is on the second and subsequent viewings you can enjoy Hitchcock’s unique long takes. It really is like watching a play and it is one of Hitchcock’s finest films, in my opinion.
The Bridge on the River Kwai. It is well worth a second watch simply to enjoy the great cinematography. This assumes you’re watching it on a large tv and preferably on blu ray.
Primer
Many of my favorites have been mentioned already, but not my very favorite: The Sting. I saw that five or six times when it was in theaters as a first run (paying 75 cents each time), and I’ll watch it again whenever the opportunity presents itself.
I just saw Gosford Park for the fourth or fifth time. On repeated viewing, you start to pick up clues about the later events in the film and a better understanding of the relationships among the characters. Actually, many mysteries/whodunits are interesting to watch a second time, to see if you can pick up clues.
The Shawshank Redemption
Apollo 13
Saving Private Ryan
LOTR trilogy
Goodfellas and Casino
Rewatch reasons:
Really good or classical actors “slumming it” in otherwise silly plots or hammy dialogue, but still applying their craft at the highest level:
Clue
Avengers/Thor/Iron Man
Galaxy Quest
Princess Bride
Legend (for Tim Curry as Darkness, pretty exclusively)
Any of the Harry Potters with a high Snape quotient
My Own Classics - I know them so well that they’re like comfort food for the mind - just lay back and quote the movie as it goes along.
Star Wars (original trilogy only)
Clue again
Fantasia
Labyrinth
Dark Crystal
Blazing Saddles
The Producers (either old or new - I like both for different reasons)
Beauty and the Beast (disney animated)
Robin Hood (disney animated)
Princess Mononoke
Laputa, Castle in the Sky
Howl’s Moving Castle
Spirited Away
Babe (the pig movie)
Oceans 11 (but only 11)
The Incredibles (animated)
Anything with Shirley Temple (I’m not proud of this, but it is what it is)
Mindless Action with Pretty People:
Transporter (any of them, really)
Thor, Thor Dark World
James Bond (mostly Pierce Brosnan, but I won’t turn down Connery or Craig either)
Oceans 12 and 13
Riddick movies
Zorro duo (with Antonio Banderas)
I’m a Sucker for Apocalypses:
Independence Day
Armageddon (the “nuke an asteroid” movie)
The Day After Tomorrow
2012
Pacific Rim
"Bad" movies I imprinted on, and I really don’t have an explanation:
Tron (not the reboot, the original)
Logan’s Run
The two live-action Ewok movies (I hate myself every time, but I can’t stop…)
Zorro: the Gay Blade
The Stepford Wives
Princess Diaries