Shaun of the Dead
Love Actually

Goodfellas/Casino
Boogie Nights
Silver Linings Playbook (new favorite, already watched the Blu-Ray four times)
Heavyweights
Batman '89
Jurassic Park
Jaws
Annie Hall
Big Trouble in Little China
Nightmare on Elm St
Drive
It's a Wonderful Life
Lethal Weapon
True Romance

My desert island movies:

Star Wars
The Empire Strikes Back
Jaws
Superman: The Movie
Back to the Future / Back to the Future Part II
Rocky / Rocky II / Rocky III
Grease
Goodfellas
Shawshank Redemption
Ferris Bueller's Day Off

Holidays:

Planes, Trains, and Automobiles
The Sound of Music
The Ten Commandments
The Wizard of Oz
A Charlie Brown Christmas

Godfather
Godfather II
Scarface (Pacino)
Goodfellas

Brewsters Millions
Midnight Madness
The Thing

LOTR trilogy
T2
The QT catalog
John Carpenter's catalog

Well, I've taken to the tradition of always watching It's A Wonderful Life for Christmas. Cliched, I now, but I still go with it.

Badder Santa - Every Christmas eve

Holiday:

Love actually
Elf
National lampoon Christmas vacation
Christmas story
Rudolph/frosty
Charlie Brown Christmas, great pumpkin, Charlie Brown

Lawrence of Arabia in 70MM.

E.T. The Extraterrestrial
The Godfather 1 & 2
Field of Dreams
Legends of the Fall
Master & Commander: The Far Side of the World
The Matrix Trilogy
The Exorcist
Halloween
Transformers
The Rock
To Live and Die in LA
Watchmen
Wedding Crashers
40 yr old virgin
Animal House
Caddyshack
Network
Chinatown
Apocalypse Now
Blade Runner
Anchorman
Black Hawk Down
Dark Knight Trilogy
Indiana Jones and The Last Crusade
The Aviator
The Departed
Pirates of the Caribbean 1-3
The Right Stuff
Bugsy Extended Cut
L.A. Confidential
Rio Bravo
The Wild Bunch
Se7en
Sherlock Holmes
Superbad
300
V For Vendetta
Miller's Crossing
There will be Blood
No Country for Old Men

Mr Blandings Builds His Dream House

Terminator 2
Die Hard
Enter the Dragon
The Warriors

That's probably it

More than just once...
Bean The Movie
A Christmas Carol 1999 (Patrick Stewart)
Jurassic Park
Back To The Future
Home Alone/Home Alone 2
Gamera/Gamera 2 (what can I say ? Steven Segal's daughter is hot)
Little Giants
Batman 1989
Terminator
The Thing
It's A Mad, Mad, Mad, Mad World
Tron
Ghostbusters
Matilda
Star Wars

LOTR Trilogy
The Nightmare Before Christmas
Snatch
Raiders of the Lost Ark
Edward Scissorhands
Pulp Fiction

Sorcerer
Goodfellas
JFK
Treasure of the Sierra Madre
The Texas Chainsaw Massacre (74)
This is Spinal Tap
The Exorcist

Pulp Fiction
True Romance
Strange Days (gotta watch it every new years eve)

Die Hard, It's a Wonderful Life, and all three Charlie Brown specials. There are some others that I might not fit in every year.

I usually work in Serenity for one of the challenges as well.

I don't watch any films once a year. I wait several years between viewings of favorites, the better to appreciate them all over again.

Hard Boiled
Irreversible
Predator
Blade Runner
Seven Samurai
First Blood
Wes Anderson films
Malcolm X
Indiana Jones films
Vengeance Trilogy
Goodfellas
Once Upon A Time in the West
Dollars Trilogy
Kubrick films
Taxi Driver
Transformers: The Movie
Superman
The Big Lebowski

These are the films that never get old to me:

Jaws
Star Wars
Empire Strikes Back
Hoosiers
Back to the Future
Field of Dreams
Raiders of the Lost Ark
Rocky
Superman:The Movie
The Terminator
Caddyshack
Slap Shot
Animal House
Ghostbusters

1. Christmas Charlie Brown
2. All of DC's Animated Movies
3. Star Wars
4. White Christmas
5. Lord of the Rings
6. V For Vendetta
7. Hoosiers
8. Superman the Movie

NY's Eve - FOUR ROOMS!

and every 6 months - THE VILLAGE

Halloween - The Boogie Man Will Get You / The Curse of Frank Black (Millennium)

I won't get down to Texas, but some people in the area might want to know where they can see Lawrence in 70mm (and annually?).

There's nothing that I have to watch, I don't plan like that, but I probably end up watching the following close to yearly.

Elf
It's a Wonderful Life
Monty Python and the Holy Grail
Halloween
The Thing
the Charlie Brown animated holiday specials