“You’ll be doin’ all right,
with your Christmas of white,
But I’ll have a blue, blue Christmas.”
Always made me think of Elvis, at home by himself, drugging himself into oblivion on Christmas Eve.
-lv
As we’ve been discussing over here, “Christmas Time is Here,” by Vince Guaraldi and Lee Mendelson, from A Charlie Brown Christmas, is, if not exactly the saddest, has a certain melancholy tone that I find quite fitting for the season. The lyrics by themselves are not sad at all, but Guaraldi’s music with its complex harmonic structure (it’s in a major key, but uses lots of ninths and major sevenths) make it just about the only Christmas song I like, and certainly the only one I can play on the piano.
How about Joni Mitchell’s “River”?
It’s coming on christmas
They’re cutting down trees
They’re putting up reindeer
And singing songs of joy and peace
I wish I had a river
I could skate away on
They sold me a dream of christmas
They sold me a silent night
And they told me a fairy story
’till I believed in the israelite
And I believed in father christmas
And I looked at the sky with excited eyes
’till I woke with a yawn in the first light of dawn
And I saw him and through his disguise
They said there’ll be snow at christmas
They said there’ll be peace on earth
Hallelujah noel be it heaven or hell
The christmas you get you deserve
Circle of Steel by Gordon Lightfoot: http://www.corfid.com/gl/Albums/Gords_Gold/Circle_Of_Steel.htm
Pretty Paper, Pretty Ribbons. 
And the cynic in me is warring with the reasonable person in trying not to rain on the Christmas Shoes people’s parade, but it’s tough. That song is the musical equivalent of e-mail glurge.
Man- so many things to comment upon…
RE the Myrrh verse of WE THREE KINGS- actually, the reality isn’t that bad but not much more appropriate. Frankincense & myrrh were ingredients in the royal & priestly anointing oils AND in the Song of Solomon, they are spoken of as scents used in …
The Royal Bedchamber! :eek:
Now try on the second verse of What Child Is This?
Why lies He in such mean estate
Where ox and ass are feeding?
Good Christian, fear: for sinners here
The silent Word is pleading.
Nails, spears shall pierce Him through,
The cross be borne for me, for you;
Hail, hail, the Word made flesh,
The Babe, the Son of Mary.
Whew… now, there are some songbooks & even hymnals that just repeat
“This, this is Christ the King, Whom shepherds laud and angels sing”. I consider
that chickening out.
I’d love to hear Coldplay’s “Have Yourself…”
Not a fan of “Christmas Shoes”- love Abbie’s comment “Jesus doesn’t care what’s on her feet” 
However, to be fair, I think the kid’s Mom was still alive, wasn’t she?
Casey1505- thanks for sharing the other perspective. Good luck to ya.
Kythereia- I only paid attention to the lyrics of Coventry Carol a few years ago- YIPES!
Father Christmas by the Kinks
It is more of an angry song but it is sad to think of people feeling that way about Christmas.
I always Do they know it’s Christmas a bit sad.
Of course standards like Blue Christmas and Pretty Paper are sad and there is a folk song called They Don’t Have Christmas in Kentucky, (IIRC).
Check out the Rhino compilation Bummed Out Christmas, containing one of my all-time favorites, “Christmas in Jail” by the Youngsters (1956). To hear the song click here, then go down to the December 8 RADD (Reindeer Against Drunk Driving) link.
On the same LP as “Grandma Got. …” is a song titled “Here’s to the Lonely” which is a mix of melancholy and hopeful generosity. It’s a pretty good song.
OK, what kind of crack was I on when I posted this? I think I heard that variant once, but the line is actually “If only in my dreams.”
Mad World by Gary Jules & Michael Andrews,our last year’s Christmas #1
They’ve taken the Tears for Fears song and stripped it down to just a piano and haunting voice.Makes you want to go find a cliff to leap off
Please, Daddy, Don’t Get Drunk This Christmas. “I don’t wanna see my momma cry.”
“O Holy Night” just shreds me. It was my grandmother’s favorite, and she died during the holiday season. 22 years later, and I still fall apart every time I hear it.
Well delphica and loach stole both of mine.
Though I think Fairy Tale of New York is sadder, if only because that seems to be the arc that MY relationships take!
Greg Lake’s Father Christmas is something else too
A local radio station starts playing holiday music starting just before thanksgiving, so I’ve come across a few that’ll choke me up:
Colorado Christmas. Mainly the chorus, the change from a driving beat to a wistful tone in just four lines is quite effective. And the fact that I usually hear this in my car and can glance over at the snow covered Rockies probably helps.
Little Drummer boy. From “I am a poor boy, too” to “then he smiled at me” always gets me.
The Gift. Probably as intentionally heart-wrenching as Christmas Shoes, but the combination of the story and music almost made me have to pull over the first time I heard it. And I didn’t realize until I just now searched for the lyrics that it’s a Garth Brooks song.
Same Old Lang Syne by Dan Fogelberg.
When I first heard this song in High School, I thought it was sad. The older I get, the more bummed out I get when I hear this one.
There’s this song called “Rudolph the Red Nosed Reindeer”.
It’s about this reindeer, Rudolph, at the North Pole who had a shiny red nose.
Well, turns out the other reindeer didn’t like him very much because of it. . . called him names, wouldn’t let him play with them. I get misty.
It turns out all right, though. He gets a little black cap that slips over his nose, so he looks like the rest of them. It carries a nice message to children that they should be like everyone else.
Not really a Christmas song, but “We Need a Little Christmas” can either make me happy or bawl, depending on my mood when I hear it.