Christmas really isn't my holiday, but I dig the spirit and music.
In no particular order, and I'm sure I forgot a dozen or two...
Pretty much any silly, spoof version of a Christmas song gets a thumbs up from me -- Walking 'Round in Women's Underwear, anything.
The Chipmunks - The Chipmunk Song
The Royal Guardsmen - Snoopy's Christmas
Brenda Lee - Rockin' Around The Christmas Tree
Bruce Springsteen - Santa Claus Is Coming To Town
Band Aid - Do They Know It's Christmas
John Lennon & Yoko Ono - Happy Christmas (War is Over)
Elmo and Patsy - Grandma Got Run Over By A Reindeer
Jose Feliciano - Feliz Navidad
Eartha Kitt - Santa Baby
Chuck Berry - Run Rudolph Run
Paul McCartney - Wonderful Christmastime
Spike Jones - All I Want For Christmas is My Two Front Teeth
Burl Ives - Holly Jolly Christmas
Lou Monte - Dominick, The Italian Christmas Donkey
David Bowie & Bing Crosby - Peace on Earth/Little Drummer Boy
Gene Autry or Burl Ives - Rudolph, The Red Nosed Reindeer
Leon Redbone & Dr. John - Frosty the Snowman (Autry and Durante are just "meh" after this)
Cocteau Twins - Frosty the Snowman
Eric Idle - F****** Christmas (NEW Holiday Classic! well not "new," but ya know)
Vince Gauraldi Trio - Linus & Lucy (sometimes, I want a continuous 10-hour loop of this, and that whole album is great)
Stevie Wonder - Someday At Christmas
Stevie Wonder - What Christmas Means To Me
Vince Vance - All I Want For Christmas Is You (not the same song as Mariah's)
Pogues & Kristy MacColl - Fairytale of New York
Kurtis Blow - Christmas Rappin'
Run DMC - Christmas in Hollis
The Waitresses - Christmas Wrapping
James Brown - Santa Claus Go Straight to the Ghetto
The Singing Dogs - Jingle Bells (yup! I'm that guy!)
Mannheim Steamroller - Deck the Halls
Bing Crosby & Andrews Sisters - Mele Kalikimaka
Maybe any of those Bing songs.
Elvis Presley - Blue Christmas (maybe the only time I can dig Elvis)
Jackson 5 - I Saw Mommy Kissing Santa Claus
Jackson 5 - Grown-Up Christmas
John Cougar Mellencamp - I Saw Mommy Kissing Santa Claus (that whole first A Very Special Christmas album)
Jon Anderson - Three Ships
Wham - Last Christmas
She & Him - Christmas Waltz, Wish... that whole album
Cee Lo & Muppets - All I Need Is Love
Ramones - Merry Christmas (I Don't Want To Fight Tonight)
Slade - Merry Xmas Everybody
Pretenders - 2000 Miles
Louis Armstrong - Zat You Santa Claus
Baby It's Cold Outside (it's been done so many times I've stopped caring which version)