I'll start:
Jingle All The Way (I know, it's horribly cheesy, but I love it!)
Elf (When the taxi hits Buddy, it slays me every time!)
Scrooged
Christmas Story
Fred Christmas
Charlie Brown Christmas (technically not a film, but...)
Arthur Christmas (Just started this year with this one.)
Christmas Vacation (By far the best of them all!)
Happy Holidays, everybody!!!
"Come on, Skip. It's go-go, not cry-cry!"
One under the radar Christmas movie is While You Were Sleeping. I love the Christmas party scene.
Sound of Music
Love Actually
Christmas Vacation
Charlie Brown Christmas
The Grinch
I try to make an effort to see all of these each December:
Christmas Vacation (Family Tradition for Christmas Eve).
Scrooge (1951) (I usually watch this late 24th/early 25th before I go to bed, on BBC's annual airing.
A Muppet's Family Christmas
Home Alone
White Christmas (Whether I plan to watch it or not, if it's played I sit down and watch it, every year)
I watched A Christmas Story every year for a long time and have gotten kind of sick of it.
These are my favorites to watch every year:
Jingle All the Way
Christmas Vacation
Bad Santa
Polar Express
The Santa Claus
The Grinch
Cartoons - How the Grinch Stole Christmas, Frosty Returns, Frosty's Winter Wonderland, Charlie Brown, Family Guy Christmas
Christmas Vacation
It's a Wonderful Life
Miracle on 34th Street - original
White Christmas
Holiday Inn
The Bells of St. Mary's
A Christmas Story
Bad Santa
Holiday Affair
The Santa Clause - only the first one
Christmas With The Kranks
Christmas in Connecticut - prefer the remake
The Bishop's Wife
Cartoons:
Garfield Christmas
Will Vinton's Claymation Christmas (these two have been a Black Friday tradition since 1993 in my family, first movies watched once the Tree is up and decorated).
Charlie Brown, and the DVD bonus feature, "It's Christmas again, Charlie Brown"
The Grinch
The Small One
Rankin Bass:
Santa Claus is Comin' to town
Rudolph (most of the Rankin Bass stuff is drivel, but these two are top notch)
Christmas Carols:
George C. Scott
Reginald Owen
Muppets
Mickey
Mr. Magoo
Albert Finney
Alistair Sim (Christmas Eve, just before going to bed)
Other Live Action:
Christmas Vacation
Miracle on 34th street, (original, of course)
White Christmas
The Night They Saved Christmas
How you can make the world a better place:
Don't shop at Wal-Mart.
-It's A Wonderful Life
-A Christmas Story
-Christmas Vacation
-The Family Stone
-While You Were Sleeping
-Elf
-The Polar Express
-Miracle on the 34th Street
-Christmas with the Kranks
-Deck the Halls (not the best but I'm a big Kristin Chenoweth fan)
-The Santa Clause series (but I'm not crazy about the third one)
-Home Alone
-Home Alone 2
TV Shows & Made for TV movies:
-A Charlie Brown Christmas
-Frosty the Snowman
-Rudolph the Red Nosed Reindeer
-Mrs. Miracle (Hallmark movie)
-Comfort and Joy (Lifetime movie)
-Holiday in Handcuffs (ABC Family movie)
-A Diva's Christmas Carol (originally a VH1 movie)
-The Christmas List (ABC Family movie)
-Christmas Every Day (ABC Family movie)
-"I'm flying high defying gravity"
-"Moo with me"
Christmas Vacation
A Christmas Story
Jingle All the Way
Elf
Saturday Night Live Christmas
Rudolph the Red-Nosed Reindeer (1964)
A Christmas Carol (1984)
Home Alone 1 and 2
The Year Without a Santa Claus
The Santa Clause
It's a Wonderful Life
Christmas Vacation
How The Grinch Stole Christmas (Jim Carey)
Bad Santa
A Christmas Carol
Love Actually
A Christmas Carol
I feel a Christmas Story is the most overrated Christmas movie ever.
I have two dollars...and a Casio.
CHRISTMAS VACATION
HOME ALONE
SCROOGED
JINGLE ALL THE WAY
MIRACLE ON 34TH STREET
A CHRISTMAS STORY
WHAT A WONDERFUL LIFE
FRED CLAUS
THE SANTA CLAUSE
Scrooged
How the Grinch Stole Christmas (Animated & film versions)
A Charlie Brown Christmas
Christmas Vacation
Frosty the Snowman
Lethal Weapon
Die Hard
The Santa Clause
Home Alone
Gremlins
A Christmas Story (I watch it every year on tv during it's 24-hour run)