-Sense and Sensibility
-High Fidelity
-Love Actually
-Tombstone
-Lord of the Rings
LA Story
Quest for Fire
The 5th Element
Stargate
Bliss
Blade Runner
The Devil’s Backbone
Haiku Tunnel
The Fisher King
Enemy Mine
Nightbreed
Oh Brother Where Art Thou
To name a few.
OH, and I forgot Pushing Tin.
Ferris Bueler’s Day Off
SAVE FERRIS!
I like to rewatch movies in which knowing the ending will require you to re-watch it to get those “Aha!” moments, like The Sixth Sense and The Others.
Other than that:
Office Space
The Jerk
Talk Radio
Groundhog Day
Shawshank
Donnie Darko
Memento
Boogie Nights
Ghost World
This is Spinal Tap
Willy Wonka
Grease
and like jjimm, Rocky Horror was re-watchable, but I haven’t seen it in a theater since 1989. The DVD can’t compare to that experience.
I too just re-watch my favorites:
The Elephant Man
Amelie
The City of Lost Children
2001: A Space Odyssey
Amadeus
Beetlejuice
Pee-Wee’s Big Adventure
Most Pixar movies like Toy Story, Monsters, Inc., etc.
And I also love to re-watch visually stunning movies where you can always catch something new every time you watch it, like the Harry Potter movies.
Neither of these are deep & meaningful but if I’m flipping channels & happen on these, I’m usually stuck till they’re over-
CARRIE (the original)
HIGHLANDER (only the first)
Rain Man
Office Space
The Back to the Future trilogy
Planes, Trains and Automobiles- I watch this one every year on the night before Thanksgiving.
National Lampoon’s Christmas Vacation- I make it a point to watch this every holiday season the way others like to watch It’s a Wonderful Life, Miracle on 34th Street and other Christmas classics.
The Breakfast Club
Lethal Weapon- At least the first two, not familiar with 3 and 4, though.
I saw it 17 times when it was in the theaters, and I’ve lost count of how many times I’ve viewed the DVD.
It is the greatest movie of this millennium, after all.
Cool Hand Luke
Fight Club
To Kill a Mockingbird
Bottle Rocket
Tapeheads
South Park: BLU
Field of Dreams
Hoosiers
Rudy
Life is Beautiful
Rocky
Schindler’s List
Saving Private Ryan
The Breakfast Club
Ferris Bueller`s Day Off
Deuce Bigalow - Make Gigalo (funniest movie ever… so far)
Highlander
Stand By Me
Dead Poets Society
Evil Dead 3
Pretty Woman
Saving Private Ryan
Ben Hur
Spartacus
Gladiator
Das Boot (in the original German, with subtitles)
Risky Business
American Pie (any of the 3)
Goodfella`s
Platoon
Back to the Future (don`t know why, but still watch it again on tv… strange)
Poltergeist
Return of the Living Dead (cos its sooooo funny)
Romper Stomper (Aussie movie with Russell Crowe… he`s a racist skinhead)
American History X
The Abyss (director`s cut, not the shortened hack job the producers rushed out to the cinema thereby ruining the whole point of the movie).
Aliens
Predator
Toy Story
Finding Nemo
Ghost
Dirty Dancing
An Officer & A Gentleman
The Good The Bad & The Ugly
The Outlaw Josey Wales
Butch Cassidy & The Sundance Kid
Rocky Horror Picture Show
Watership Down (mainly because of the brilliant story… it desperately need`s to be re-made though).
Star Wars
Indiana Jones (Raiders of the Lost Ark)
Pirates of the Carribean
Porky`s
Home Alone
Footloose
Jeepers Creepers
Shrek
LOTR trilogy
These are some of the movies I can watch every year or so and not get too bored.... probably think of alot more later. Not too many recent movies though, or very old ones… kinda stuck in the 80s/90s I guess. Would have liked to have added Troy to the list but it ended up being not too good :( Pity some movie producers dont take up a David Gemmell book… any of them would be brilliant.
Oh, absolutely. If you only watch this movie once, you’re going to miss so much! It’s a lot more fun the second time (and third, and fourth…).
Movies that merit periodic re-watching?
Airplane!
Airplane 2!
Some very good movies in these lists. Allow me to add:
Repo Man
And dropping further back into the past:
Some Like It Hot
High Noon
The answer to this, like so many movie-oriented questions, is:
The Iron Giant
In addition, and not mentioning the many that others have mentioned:
Wayne’s World
Bring It On
Run, Lola, Run
Terminator 2
A lot of the best are already up there. If I had to take only one movie to a desert island, it’d probably be “The Princess Bride.”
My other choices:
Cold Comfort Farm
Sirens (a personal weakness, but I love it)
The Shining
The Piano
Casablanca
Mulholland Drive
Room with a View
Crouching Tiger, Hidden Dragon
David Copperfield
The Harry Potter movies
Apocalypse Now
Thanks to RealityChuck for remembering “The Fatal Glass of Beer.” My God, that thing’s funny.
I will now fill in the blank you have all left out:
Harold & Maude
You are welcome! 
[QUOTE=dwc1970National Lampoon’s Christmas Vacation- I make it a point to watch this every holiday season the way others like to watch It’s a Wonderful Life, Miracle on 34th Street and other Christmas classics.[/QUOTE]
Me too!
And, in addition to the other great ones (particularly my all-time favorite, Amadeus that have already been named that I like to re-watch:
Boogie Nights
Gone With the Wind
Magnolia
Stealing Harvard
Austin Powers
Dr. Zhivago