Also Bruce Cockburn and Jorma Kaukonen.
Simon and Garfunkel: Silent Night/7o’clock News
Another anti-vietnam war xmas song from around the same time (novelty type):
We have the very first one, and play it every year. It’s a perfect combination of tunes we like matched with artists who do a great job with their chosen song. Particular favorites are the Stevie Nicks version of ‘Silent Night’ and Madonna’s ‘Santa Baby’.
I also like The Gift, Mannheim Steamroller Christmas and Trans-Siberian Orchestra’s Christmas Eve and Other Stories (which is kind of cheesy, but in a good way).
Funny stuff:
Dr. Demento Presents: The Greatest Christmas Novelty CD Of All Time
My faves: “I Want A Hippopotamus For Christmas” and “I Saw Daddy Kissing Santa Claus.”
Pentatonix’s “That’s Christmas To Me” album, one of the biggest selling albums of last year (and again this year already).
Straight No Chaser has a couple good holiday albums too - I have the first one.
Contains such classics as:
I Am Santa Claus
Walking 'Round In Women’s Underwear
I Came Upon A Roadkill Deer
and many others.
From the sublime, The Medieval Babes:
The Holly & the Ivy
In Dulce Jubilo
Coventry Carol
to the ridiculous, Rudolph the Red-nosed Reindeer sung to the melody of Free Bird by Rocket Park
Kate Miller-Heidke covering Tim Minchin’s White Wine In The Sun.
Tripod’s I Hate Your Family. Jump to about 35 seconds in.
I came in here to recommend Gary Hoey’s “Ho! Ho! Hoey: the Complete Collection.” That is the best rendition of “You’re A Mean One, Mr. Grinch” you’ll ever hear.
Also, everyone needs to hear King Diamond’s No Presents For Christmas. Although it’s not very cheery.
I’d say Trans Siberian Orchestra, too, but they’re hardly below the radar.
Loreena McKennitt has recorded plenty of non-standard Christmas songs…Midwinter Night’s Dream is one of my favorite albums.
And because there’s no tradition like a new tradition, how about the acapella chorus version of (Let’s Have) A Patrick Swayze Christmas?
Some from the other side of the Pond:
Jonah Lewie - Stop the Cavalry: bit of an oddity, an anti-war Christmas song with a video set in the WW1 trenches released on a label better known for bands such as The Damned and The Pogues, and artists as diverse as Elvis Costello and Bob Marley. An oddly bouncy number considering the sentiment.
The Pogues - Fairytale of New York: Ahh, Kirsty MacColl. Bless.
Steeleye Span - Gaudete: If plainsong sung with an occasionally West Country accent* is your thing.
Wizzard - I Wish It Could Be Christmas Every Day: 70’s British Glam Schlock at its “finest”.
The Darkness - Christmas Time (Don’t Let The Bells End): Serious rock band, or massive piss-take of 70s American hair metal - you decide.
- Think British version of “redneck”.
I love good music, of all types. The only thing I cannot stand is standard Christmas music. My sister in law and a woman who sits near me at work both play this dross for weeks each year. So I introduced them both to the fine works of Putumayo World Music and we are all happy now.
Jazz and Blues Christmas, New Orleans Christmas and plenty of others are on youtube.
The Harry Connick, Jr. Christmas album is great. So is the one by Yo Yo Ma and friends.
I have posted a link in other years to this experimental piece from Mom and Daddy. It is a bit abrasive in the middle, but listening to it loud just blows me away every single time. When I used to do a radio show on the local public station, I would play this every year on my last show before Christmas and it never failed to get a response— sometimes positive and sometimes negative. If you like Christams music and are not opposed to something very out of the ordinary… give it a listen.
The late Tommy Thompson of the Red Clay Ramblers wrote “Hot Buttered Rum”
When chimney smoke hangs still and low across the stubbled fields of snow
And angry skies reach down and seize the sorry blackened bones of trees
In the dead of winter when the silent snowbirds come
You’re my sweet maple sugar,honey, hot buttered rum…
Moody rather than cheerful; YouTube has versions. If you don’t own any Red Clay Rambler albums…
Brave Combo, that Nuclear Polka Band from Denton, has It’s Christmas, Man. Their first Christmas album. Listen to some of the tunes here. Or find out when they’ll play your town.
Not too obscure–Joan Baez’s Noel. With music arranged by Peter Schickele–AKA P.D.Q Bach. Released in 1966, the album surprised many because of its simple beauty…
My initial reaction was “70s?? Duh, it’s an 80s song!” but Wikipedia quickly informed me that I was heretofore only familiar with the 1984 re-release. I distinctly remember watching it on Top of the Pops that year, as a young teen.
It will always be an 80s song to me. 
Charles Brown - Please Come Home For Christmas
The Eagles do a great cover of it too.
Charles Brown - Merry Christmas Baby and it sounds great when Bonnie helps him out.
Snow Angels by Over the Rhine is probably the best all-originals (i.e., no standards) Christmas album I’ve ever heard. (Well, there’s a tongue-in-cheek reworking of “Jingle Bells,” but close enough.) “Darlin’ (Christmas Is Comin’)” is one of my all-time favorites.
The Spirit of Christmas by Ray Charles: also stellar. Every track kills. He even makes “Rudolph the Red-Nosed Reindeer” enjoyable, and I hate that song.
Paste magazine’s Christmas comps are usually good, and the 2012 one in particular was killer.
Christmas Remixed - Holiday Classics Re-Grooved. Sounds like it would be cheesy, but really very good.
Merry Christmas by Johnny Mathis, for when you want to go old-school with the master. Better than Nat King Cole for my money.
And what would Christmas be without James Brown to make it funky?
That takes care of the albums; here are some single tracks worth adding to your holiday mix:
“All That I Want” - The Weepies
“Christmas After All” - Maria Taylor
“Why Can’t It Be Christmas Time All Year” - Rosie Thomas (her album is good, if not quite a classic)
“Peace at Last” - Hem (almost unbearably beautiful)
“Thanks for Christmas” - XTC
“Uncle John” - Jonathan Coulton & John Roderick. Hilarious.
“Everything’s Changed at Christmas But You” - Drew Holcomb & the Neighbors. What Christmas means as you get old. Prepare to weep into your egg nog.
I may post more if I have time. I’m a bit of a Christmas music fiend.