I’m sorry, but all I can think after reading the lyrics to the song is that the narrator was a victim of a scam. “Oh no, I can’t get my dying mother a pair of shoes! How will she die happy now?” The kid was probably back in the store an hour later, returning the shoes for a cash refund. Ah well, I’ve still got my retail loss prevention instincts to keep me warm.
blue christmas by elvis presley
Prayer of the Children never mentions Christmas, or even winter, but the hauntingly beautiful four-part men’s choir version of it is on the playlist of the local Christmas Music station.
I’ll second “Christmas Shoes”. The one line that always gets me is “If Momma meets Jesus tonight”. The worst is when it plays at work and I start tearing up in front of the customers.
Try listening to it sung by a high school choir performing at your company’s Christmas luncheon. The table behind me was full of IT guys and they were sniffling like mad by the end. One lady (who lost her mom a year before said luncheon, to the day) had to leave the room and sob in the hallway. Seriously, WTF?
Dangit…almost forgot about that one. I kinda wish I had—thanks for tearing open old wounds. ( 
)
Anyway, how about…El Vez’ Christmas Wish? Possible SPOILER-ey details in this post. A sample from iTunes really wouldn’t do it justice…it’s the last ten seconds or so that turn it from “vaguely melancholy” to outright spooky.
Pardon me but the OP wants depressing songs, not glurge.
Okay that did it.
I’ll be back later. I need to go hug my cats and try not to get them all wet. 
You did warn me. Why oh why oh why did I click that link?
If I throw up, I wonder if the cats would eat it…
Please, Daddy (Don’t Get Drunk This Christmas) - John Denver
“I don’t wanna see my momma cry…”
and
Same Old Lang Syne - Dan Fogelberg
not too depressing until the final lines:
“Just for a moment I was back at school,
And felt that old familiar pain…
And as I turned to make my way back home,
The snow turned into rain…”
This is one of two Christmas songs that has made me cry. The other is Santa I’m Right Here by Toby Keith. And I like sad Christmas songs - Coventry Carol and Christmas(Baby Please Come Home) are two of my favorite Christmas songs.
I’m always surprised to hear of otherwise rational people who are so “moved” by this song. It just chokes me up in that “gotta find a barf bag” way.
Did you know they’ve got a book based on the song now? Blegh.
Nothing says “holidays” like a hit-and-run on an elderly woman!
Yeah, yeah, I know. Pure and utter schmaltz.
But I’m powerless against sad cat-related schmaltz. I can’t help it.
And a movie. With Rob Lowe.
Usually I am, too.
But I don’t want my cats curling up with mice in the spirit of Christmas. I want them to kill and eat the buggers, the way cats are supposed to do.
I really don’t want to think that my cats might do anything with mice or rats other than kill them. If I assume they would kill any rodents they found, I can say that the fact that I’ve never seen them with a dead rodent must mean that my house is rodent-free. If my house isn’t rodent-free… :eek: If I find a mouse or rat in the house, I will scream loudly enough that people in Australia will be saying, “Keep it down”.
“I’m Walkin’ Through Your Town Tonight” – just heard it on Prairie Home Companion. I looked for the lyrics but couldn’t find them, darn it. Lonely old hobo, looking for someplace warm to spend Christmas.
Well, of course John Cash is gonna have a sad Christmas song… “Christmas As I Knew It”, from his album “The Christmas Spirit”. Bittersweet depressing, as it wasn’t just schmaltzy writing about Christmas situation, but true from Mr. Cash’s experience. It’s about making do, but then the last lines kinda crush the bit of joy found: