I tire of Christmas music pretty quickly, but I do have some lasting favorites:
Wham’s “Last Christmas.” Seriously. I don’t know why.
Sarah McLaughlan’s version of “Song for a Winter’s Night.” It’s lovely and occasionally gives me goosebumps.
Amy Grant’s “Little Town.” I love her different melody.
Bruce Springsteen’s “Merry Christmas Baby,” mostly for the nostalgia (my family played that Very Special Christmas tape over and over and over when I was little) and partly for the sassy saxophone.
WOW!
just… wow.
you were RIGHT.
I am mostly a traditionalist. I especially like Nat King Cole. I like Mindy Smith’s and Sufjan Steven’s Christmas albums, which contain some originals. I think I am the only person who actually likes Grandma Got Run Over By A Reindeer. My favorite might be Merry Christmas From The Family by Robert Earl Keen. Finally, I recently discovered the world of Xmas mashups. The first one I heard was Roxanne vs. Rudolph (“Rudolph, you don’t have to turn on the red light…”) Utterly brilliant.
The Night Santa Went Crazy - ‘Weird’ Al Yankovic
Oh Holy Night. The first time I heard it sung by an operatic tenor it brought tears to my eyes. I’ve only had that reaction to a few voices.
Also, O Come All Ye Faithful, Riu Riu Chiu (my cousin’s rendition), and Silver Bells because it reminds me of driving home from my grandparents house and seeing the city all lit up.
Lennon’s Happy Xmas (War Is Over). It is about the only song I know of that manages both to be a true Christmas song, and still have some edge to it.
Putumayo World Music have an array of Christmas music with novel arrangements, unfamiliar instruments, world music songs that is a refreshing change. Even the boring old standards sound good. Listen to the track samples.
I buy them for my sister-in-law. She is a school principal and plays them for the kids each year.
Christmas Wrapping by The Waitresses, 1981. That video link includes a relatively outrageous light display.
The intricate lyrics make it an impossible sing-a-long, but it’s a thoroughly catchy pop-rock number, and the horn section is fantastic.
The song starts off mildly cynical, but it’s actually a rambling love story.
Can I count the one about feeling like “the only kid in town without a Christmas tree”? Something about how “you don’t need ‘Deck The Halls’ or ‘Jingle Bell Rock’…”
Christmas Time is Here, as done by Dave Benoit
Carol of The Bells, by most anybody
Hey, Santa Claus, by The Platters
If you like Weird Al, try Christmas at Ground Zero.
My sister just sent me a link to the Christmas Can Can, and it’s a hoot.
God Rest Ye Merry Gentlemen by the Ian Anderson Band.
mmm
I hard a live version of this by Tull on satellite radio (Deep Tracks, where else) the other night and loved it. Less flashy than the version you linked to.
Christmas Must Be Tonight by The Band.
O Holy Night is good, but ONLY if sung by a male. (yes it’s sexist, but women can’t sing the song for crap).
I’ll second “Christmas Wrapping” by the Waitresses, and add everything from The Ventures Christmas Album. Between the Ventures and Tis The Season for Los Straightjackets, my christmas cheer just comes bubbling up to the top.
Also, John Lennon’s So this Is Christmas gets to me everytime I hear it. I absolutley love it, and can not listen to it all the way through withought tearing up.
I mostly go for non-traditional ones, like “Fairytale of New York,” both Weird Al X-Mas tunes, etc…
Even the “traditional” ones I prefer to be a little off-kilter…I mean, everyone knows the single best Christmas album ever is John Denver and The Muppets.
Rolf the Dog and John’s rendition of “Have Yourself a Merry Little Christmas” is damn near perfect…it captures a weird sadness and essence of loneliness…every time I hear it, I imagine an old soul, by himself on Christmas, staring into the fireplace and slowly sipping a scotch, wondering where all the time has gone and why everyone has passed him by. 
I actually like most of them, new and traditional. About the only ones I don’t like are “Have Yourself a Merry Little Christmas” and “Chestnuts Roasting on an Open Fire.”
I rather liked Stephen Colbert’s “Another Christmas Song.” Very clever and cynical. And even though I’m not what you’d call much of a fan of rap music, Run-D.M.C.'s “Christmas in Hollis” has a nice groove to it.
The Sufjan Stevens Christmas album, in particular his renditions of O Come, O Come Emmanueland Hark the Herald Angels Sing.
I also like the Christmas Song by Dave Matthews and Christmastime is Here (aka, the theme from the Charlie Brown Christmas Special) by Vince Guaraldi.