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does Weird Al's 'Nature Trail to Hell' count? After all, it opens with,

"Coming this Christmas to a theater near you..."
None of them belong on the same list with 'Christmas Shoes'

http://www.youtube.com/watch?v=GJcPVB-we7g

I've never heard a more manipulative piece of deliberate heartstring yanking. Unlike 'Bells for Jim', there ain't no happy ending. Anything else I could say would be spoiler.
I have disliked, nay despised, "Christmas Shoes" since the first time I heard it. What young(ish) child is going into a store - alone - with a pocketful of change to buy shoes for his dying mother? How did he get there? How is he getting to the hospital after? I can't check my brain at the door. The whole scenario screams "SCAM" and the cashier/other customers as being "marks". This is one song on my "turn the radio off, I'm gonna heave" list.
When The Pogues teamed with the late, great, and dearly-missed Kirsy MacColl to record "Fairytale of New York", a class was born:

http://www.youtube.com/watch?v=NrAwK9juhhY

"You scumbag, you maggot, you cheap lousy ******, happy Christmas my arse"
I too fully expected to see this one on the list.
"Christmas eve in the drunk tank ..." starts the song out. There are threads of hope, but it is an emotional roller coaster, mostly down.
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Great list! I just listened to John Prine this weekend. I got a strange thrill out of it.
Also good: "Please Daddy Don't Get Drunk This Christmas." This song may be funny for some people; for others, it's a page from the family photo album. I have to agree about "Christmas Shoes" too.
"Christmas In Jail" 1956, The Youngsters. Probably on youtube, but not sure.
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Best of set
josmyth 12th Dec
I vote for John Prine.
Christmas is near and I found this; http://www.youtube.com/watch?v=dtszN3TkQsI

Or not..

Merry Christmas
"Christmas Gets Worse Every Year" by The Other Ones
http://www.youtube.com/watch?v=9YvZn1hgIvo
"Chipmunks roasting on an open fire" is a nice change of pace from the saccharine as well.
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"Chiron Beta Prime". Ah, Christmas and Soylent Green, is anything better?
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John Lennon
RipVan Updated - 14th Dec
What about "And So This Is Christmas?" At least I think that's the title. Nothing like hearing that to bring you down. Sux.

And that Paul McCartney attempt at a Christmas song "Simply Having A Wonderful Christmas Time." It isn't supposed to be a downer, but the synthesizer and his mindless pop lyrics and singing take all of the humanity out of the song. It rings as empty as the opening notes and never brought me any joyl It just sounds so empty! Don't worry if you don't agree with me on that one, I have mentioned that lifeless song to others and they don't feel the same way. Oh well...

Edited for speeling.
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For me that song (simply having a wonderful christmas time) is vacuous, tedious and mediocre. Not only is it not joyous, it actively removes joy from my soul when I hear it.

It may as well be a washing powder jingle or lift (elevator) musak
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"And So this is Christmas" has been rumbling around in my head as well. Quite depressing, blues without the blues.
This is the ultimate Xmas downer song - http://www.youtube.com/watch?v=cnRmHszDaa0
By Miles Davis and Bob Dorough
Sample Lyric Blue Xmas:
you see right through,
All the waste, all the sham, all the haste
and plain old bad taste
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This weekend on a radio show, American Routes, I heard an interview (and this song too) with Bob Dorough. Notably, I learned that he is the same guy behind all of the old Schoolhouse Rock songs.
Nat: http://www.youtube.com/watch?v=UePxqqNGsNw "He's the little boy that Santa Claus forgot"

Stan: http://www.youtube.com/watch?v=chTMOuuUZi4 "First Christmas away from home"
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And we shouldn't forget Jethro Tull's "A Christmas Song". "How can you laugh when your own mother's hungry? How can you smile when your reasons for smiling are wrong?"
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Oh, bawls!
RipVan 21st Dec
I should have included that in my list above. HOWEVER, I have the excuse that they play the other two songs on the radio every season. I don't hear Tull's song at all anymore, but I think I'll give it a listen, since it has been so long. But I agree, and put this one right next to John Lennon...
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Merle Haggard -- "If We Make It Through December" should top your chart as the tear-jerker of all time. A classic gut-wrencher with that glimmer of hope that those in such a position cling to. If you want to feel sad (and sometimes, right? That's what this article is about so admit it!) this is a "go-to" country song.
is conspicuous in its absence, if you ask me. It was on a blues/R&B X-mas compilation in the 70s....I think it was by Freddie King. It's still part of my set this time of year (along with Chuck Berry 'Run, Run, Rudolph', J. Prine 'Christmas in Prison'---see above, and Royal Guardsmen 'Snoopy's Christmas'). Remember to tip your waitresses and bartender, and enjoy the rest of the show......
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You should be as good at what you do as Tom Waits is.
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Seems there should be recognition of the "stealth downer" songs.... the ones that get played over and over as if they happy, uplifting songs; that is, until you listen to the lyrics. I'm thinking of....

"Last Christmas" by Wham!
"We Need A Little Christmas" from Mame (lyrics: "Put up the tree before my spirit falls again....For I've grown a little leaner, Grown a little colder, Grown a little sadder, Grown a little older")
the abovementioned "So This Is Christmas" (or is it, "Happy Xmas (War Is Over)"?)

Back to the un-stealthy ones, "Do They Know It's Christmas" is worth mentioning.

And coincidentally enough, all the above have been on Glee Christmas albums. Hm.
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Every time I hear that song, I cannot help but think "Do they CARE it's Christmas?". Christmas is a Christian tradition. To the Muslim, it's a pagan holiday. Not only do they not participate in it, they avoid it altogether (well, the Muslim I know, at least, my next door neighbors included).

In mostly Muslim areas, Christmas must be like Ramadan for Christians: if they know it's the Season, they certainly don't care. This attemp at tear jerking is supposed to entice generosity, but to me it simply shows utter ignorance of other cultures.
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My favs: "Christmas at Ground Zero" (W. Al), and "It's hard to be a Jew on Christmas" (Southpark)
"The Night Santa Went Crazy", although that one won't get any play this year due to current events.
I borrowed Shuggie54's suggestion of Miles Davis. Tom Waits and "Little Boy that Santa Claus Forgot" were carryovers from the last mix. Also new this year is the song by Donovan, which I only recently heard for the first time. The mix is simply titled Anti-Xmas 2012, and it's mostly alt-punk and comedy themed, with eclectic variety. A mix CD is a cheap gift for acquaintances, and more lasting than a card.

This year's track list:
01 Father Christmas by Action Action (The Kinks cover, original is better)
02 The Season's Upon Us by Dropkick Murphys, (released this year)
03 Merry Christmas I don't Want To Fight by The Ramones
04 I Won't Be Home for Christmas by Blink-182
05 Yule Shoot Your Eye Out by Fall Out Boy
06 You Ain't Getting S**t For Christmas by Red Peters
07 Homeless on the Holidays by Bob Rivers
08 A Christmas Carol by Tom Lehrer
09 Another Christmas Song by Stephen Colbert
10 I Don't Believe In Christmas Anymore by Donovan
11 Blue Xmas (To Whom It May Concern) by Miles Davis & Bob Dorough
12 Christmas Without Weed by Phish
13 I Wish You Would Roll a New Blunt by Afroman
14 December Is for Cynics by The Matches
15 Christmas Sucks by Tom Waits & Peter Murphy
16 This Time of the Year by Project 86
17 It's A Wonderful World by Nick Cave & Shane Macgowan
18 The Little Boy That Santa Claus Forgot by Unknown (Perhaps Nat King Cole?)
19 Silent Night/Christmas Card from a Hooker In Minneapolis by Tom Waits
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Is one of those yours?
by ELP

They said there'd be snow for Chrsitmas
They said there'd be peace on Earth
But instead it just kept on raining
A veil of tears for the virgin birth

It's my favorite cynical/see thtough the BS song.

Then there's the Pretender's version of "Have Yourself A Merry Little Christmas" wherein Chrissie Hynde comes as close to crying as I've ever heard her.

A couple more
River by by Joni Mitchel (or anyone else)
Christmas In Vietnam by Johnny & Jon
Christmas Eve Can Kill You by The Everly Brothers
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