For sad, the only one for me is "Have Yourself a Merry Little Christmas," by any artist who uses the actual lyric instead of that "shining star upon the highest bough" BS.

For sad, there's just the one: "Where Are You Christmas?" By Mariah or Faith Hill

My Personal Top 3:

1: Christmas With the Devil by Spinal Tap
2: Christmas at Ground Zero
3: The Night Santa Went Crazy

both 2 & 3 are by Weird Al Yankovic

The Christmas Song by Mel Torme when he was 19 years old!

also love the Nat King Cole version, but no others!

Justin Bieber and Busta Rhymes "Drummer Boy"

Kelly Clarkson "favorite things"
Also the Brian Setzer Orchestra does this, it's a cool arrangement

Oh Holy Night

Carol of the Bells by the transyberian orchestra

I wish more original songs would come out.

Christmas Canon? And the on ex out skating away on a river

Anonymous wrote:Mahalia Jackson's version of O Holy Night: https://www.youtube.com/watch?v=KVxI7Ul4lnk

Her Christmas albums are just gorgeous.

OMG. beautiful. I'm the complainer about Josh Grobin about waiting for the climax, and this song satisfies me

Anonymous wrote:Wham! Last Christmas, even though it doesn't make any sense

I love this song unironically. And the video is so ridiculously 80s. I also love The Waitresses' "Christmas Wrapping."

More recent songs I've liked:
Weezer, "O Holy Night"
Bare Naked Ladies and Sara McLachlan, "God Rest Ye Merry Gentlemen/We Three Kings"
Dido, "Christmas Day"
Sufjan Stevens has some great Christmas songs.

I really love Advent and Christmas hymns, especially "O Come, O Come Emmanuel," "O Come All Ye Faithful," "Joy to the World," "Hark the Herald."

Anonymous wrote:most of the Christmas with the Rat Pack CD

I LOVE Baby It's Cold Outside. Hilarious!

Also, the SNL version:

http://www.nbc.com/saturday-night-live/video/baby-its-cold-outside/n44614

Here's a list I googled for 100 Christmas songs --
http://digitaldreamdoor.com/pages/music0_christmas.html

Santa Baby by Eartha Kitt

most of the Christmas with the Rat Pack CD

I LOVE Baby It's Cold Outside. Hilarious!

The Christmas Song by Nat King Cole

The entire album with the Muppets and John Denver.

Wham! Last Christmas, even though it doesn't make any sense