Favourites :
White Christmas
Stop the Cavalry
Last Christmas
Santa Claus is Coming to Town
Silent Night
Driving Home for Christmas
Not much of a fan of Little Drummer Boy, though.
There’s nothing in this song that denotes Xmas, but, “Little Altar Boy,” is on the Carpenters (revised) Xmas album and Karen sings the pants off it.
Not really being into that whole Christmas thing, I can only think of one choice for best: Christmas with the Devil.
This is my new favorite Christmas song. “Oh, yeaaahhhh.”
I’m going against the grain, but:
Worst: Do They Know it’s Christmas?
It’s a forced follow up to We Are The World which was great and a poke in the eye to the billions of non-Christians around the world.
“We’re thinking about you one day out of the year!”
Edit: Best: Merry Christmas Darling
My favorite? Christmas in Dixie by Alabama.
Wrong way around: Do They Know It’s Christmas? came first in the UK (recorded November 1984), then Michael Jackson and Lionel Ritchie cranked out a US version in January 1985.
And they’re both terrible songs.
Best: “Carol of the Bells”. Sometimes I prefer vocalists singing a capella, sometimes I prefer a carillon with no vocals at all.
Generally, I prefer traditional arrangements, with choirs and orchestras; or with one or two singers, accompanied by a few acoustic instruments.
I am generally less fond of the jazz/rock/pop versions.
Although “We Wanna See Santa Do the Mambo” is too jaw-droppingly silly to be offensive (to me, anyway).
I only like ‘Baby Its Cold Outside’. WTF. And ‘O Holy Night’ by about anyone, especially Celine Dionne and Mr. Michael Crawford. I had the Trans-Siberian Orchestra on a CD in the car which literally saved my sanity on Christmases past with my horrible family - I would go out to ‘get some air’ and listen to ‘Carol of the Bells/Sarajevo’ and regain the will to live again…Oh, and ‘White Christmas’ by Mr. Clyde McPhatter still sends waves of luv through me, and Annie Lenox ‘God Bless You Merry Gentleman’ - the video! A hurdy gurdy and pagans and the horned god at the end, I watch it on youtube every year, how I love it.
Just heard some shittery on a Pandora commercial, as trite as trite can be, ‘Piece of My Heart’ by Steven Maglio. Extremely stupidly boring and cliched, written with a rhyming book in one hand. .
The one with some goober in a truck drivin’ on home for Christmas, I hate it so much, I can’t think of the title.
Jingle in the Jungle surely fits on one of those lists.
Best - Frosty the Snowman by Leon Redbone and Doctor John, although the Jimmy Durante TV version is good also.
Worst - Tina Sinatra doing ‘Santa Claus is Coming to Town’. How Frank’s kid could have so little soul, rhythm and ability to sing on key is a marvel of genetics.
Last night in a restaurant, I heard a version of “All I Want for Christmas is My Two Front Teeth” which was sung by a grown man with perfect enunciation. 
Bizarre.
BEST
Wassail Song
O Holy Night (when done properly)
(another O Holy Night also done properly)
I Wonder as I Wander
Mary, Mary
Coventry Carol
WORST
Rudolph the Red Nosed Raindeer (any version)
Jingle Bells (any version)
Last Christmas
Ten Thousand Joys
We Need a Little Christmas
All-time worst: Jay North as Dennis The Menace singing Silent Night
Current best: Davy Jones singing Mele Kalikimaka
The best is more of a reading than an actual song, although there is background music. The Mark and Brian radio show would have a Christmas special in which The Polar Express would be read by a different celebrity each year-This is a compilation of some of the best readings.
Another holiday recording I listen to every year is a half hour radio play from the Rick Emerson Show that used to air here in Portland-Santa Claus: Behind The Christmas
I mention this most years, Christmas Must Be Tonight by The Band doesn’t get the play it deserves.