Turning to the people with the best taste on the internet.
I’m attempting to put together a list of the most bestest Christmas or winter holiday music out there. What would be the recommendations? Genre doesn’t matter…I’m kind of looking for superior versions of any individual song, even if there’s more than one great version, so recommend anything you can think of: country version, instrumental version, whatever.
For me, the standard is Elvis’ version of Blue Christmas.
Might as well get the titans of the genre out of the way:
“White Christmas”, Bing Crosby
“The Christmas Song”, Nat “King” Cole (aka colloquially as “Chestnuts Roasting Over an Open Fire”)
“Rudolph, the Red-Nosed Reindeer”, Gene Autry
“O Tannenbaum”, Johnny Mathis
“Silver Bells”, Burl Ives
“Little Drummer Boy/Peace on Earth”, Bing Crosby & David Bowie
“Feliz Navidad”, Jose Feliciano
Trans Siberian Orchestra - Wizards of Winter
Manheim Steamroller - Deck the Halls, God Rest Ye Merry Gentlemen, Carol of the Bells to name a few.
Joan Jett - Little Drummer Boy
Enya - Silent Night (Irish)
Kathleen Battle singing Lo How a Rose E’er Blooming if you can find it.
John Denver - Noel, O Holy Night if you can find them.
Also, believe it or not, The Monkees - Riu Chiu isn’t bad.
Jussi Bjorling - O Helga Natt
Obligatory Carols for a Cure plug. Great music, great cause, great prices.
the Ventures Christmas Album is one of my favorites, and in the same vein, Los Straightjackets have a Christmas album that is simply awesome!
Carpenters - “Christmas Collection”
The entire album is just wonderful, but most lovely is Karen Carpenter singing “I Heard The Bells on Christmas Day.” Her voice in that song is so pure, so clear, so…I don’t know, it’s just particularly resonant and beautiful.
sigh I really miss her.
There’s a lovely album of John Denver and the Muppets doing Christmas carols. Denver has a lovely voice, and there’s something so plaintive about a Muppet singing about peace and love that it’s irresistible. Also, Peter, Paul and Mary do a very nice Christmas (well, holiday, I suppose, because there’s some wonderful Chanukah songs as well) album with the Mormon Tabernacle Choir.
For individual songs? The Nitty Gritty Dirt Band has a beautiful song called “Love Has Brought Him Here” that really defines the season for me.
Jars of Clay does a great Little Drummer Boy. I like it, anyways…
Brendon Small
My favorite “What Child Is This” is Joan Sutherland’s. It has appeared on other collections. She also does hit a high E flat (AFAICT) at the end of “O Holy Night”.
“A Robert Shaw Christmas - Angels On High” and “Songs of Angels” (also Robert Shaw) are the very good Christmas carol CDs. If you can get his “Christmas with the Robert Shaw Chorale” (issued by the Musical Heritage Society, a re-issue of an LP), CD 2 has earlier recordings of the carols on “Songs of Angels”, and IMHO the performances are a tad better.
Best and worst Christmas songs Best And Worst Christmas Songs - Cafe Society - Straight Dope Message Board
What is your favorite Christmas CD? What is your favorite Christmas CD? - Cafe Society - Straight Dope Message Board
Recommend some holiday music for me! Recommend some holiday music for me! - Cafe Society - Straight Dope Message Board
I love everything on Leon Redbone’s Christmas Island, which includes a lot of standards and two originals, Christmas Ball and That Old Christmas Moon, which may be two of my favorite Christmas songs ever.
The Waitresses – “Christmas Wrapping”
Bruce Springsteen – “Santa Claus is Coming to Town”
David Bowie and Bing Crosby – “The Little Drummer Boy”
Don’t forget “Walkin’ 'Round in Women’s Underwear.”
This one gets stuck in my head:
http://www.santasearch.org/music.asp?PID=2&AudioID=1763
(John Lenin “Happy Christmas”)
Not being religious:
Second “christmas wrapping” the waitresses.
any of the Charlie Brown Christmas tunes by vince guaraldi
"a christmas song’’ and “solstice bells” Jethro tull
“Greensleeves/what child is this”
“carol of the bells”
You mean THIS song? 
My standard answer to this question is
“Fairytale of New York” by the Pogues.
It’s hands down the best Christmas song I know.