My friend and I were discussing sad Christmas songs tonite and the one we both agreed on was “Have Yourself A Merry Little Christmas” by Judy Garland. Whenever I hear that song, I feel like having a good cry.
Another song that makes me a bit sad is “Jingle Bells”. We used to sing that song in Kindergarden and it just makes me remember a time when I was so young and innocent. (LOL) Those days are long gone. 
Any other sad Chistmas songs? Any other unlikely sad Christmas songs?
Eric
“Grandma Got Run Over By A Reindeer” is kind of sad. Poor Grandma…
So is “It Came Upon The Midnight Clear”.
The Pretenders’ version of “Have Yourself A Merry Little Christmas” makes me well up.
This reminds me of the Pretenders song “2000 Miles”. Makes me sad.
“I’ll be home for Christmas”
The ending line (“if only in my dreams”) shows that no, the singer really won’t, but wishes he/she would…
not happy at all.
Same with “I’m dreaming of a white Christmas”
Coventry Carol. It’s about Herod’s slaying of the children after Jesus’s birth, and it never fails to bring tears to my eyes.
The verse about myrhh in “We Three Kings”.
" Myrhh is mine, its bitter perfume
breathes a life of gathering gloom
sorrowing, sighing, bleeding, dying;
sealed in the stone-cold tomb. "
You’re giving this to a baby? Yeah, I know it’s foreshadowing and all, and it doesn’t make me tear up, but it’s depressing.
Nothing comes close. I actually teared up the first time I heard it.
I’ll Be Home for Christmas - people seem to forget that the last line of the song is “Well, maybe next year.”
I just heard that one for the first time a few weeks ago. I didn’t like it because it was so obviously manipulative — a planned tear-jerker.
As for “Have Yourself a Merry Little Christmas” — my Mom always pointed out that it technically is not a Christmas song at all. In the movie it was in, it was sung in the summer time — I think that the sadness was due to the fact that they weren’t going to be together at Christmas, so the message was to “Have yourself a merry little Christmas NOW.” (I’m not really familiar with the movie, so perhaps a movie buff can jump in and explain the exact circumstances.)
It’s from Meet Me In St. Louis, and I think the contradiction is supposed to be that the Christmas is NOT in fact merry, because the Smith family has just learned that they will be moving away from St. Louis. Tootie, the little girl, is crying because Santa won’t know how to find her next year. I’m pretty sure it’s wintertime though, because Judy Garland is looking out over a snowy yard when she sings.
My own pick for saddest Christmas song is Fairytale of New York, first because it is a sad song, and second because it makes me think about poor dead Kirsty MacColl.
It’ll be lonely this Christmas
Without you to hold
It’ll be lonely this Christmas
Lonely and cold
It’ll be cold, so cold
Without you to hold
This Christmas
Always made me cry.
Name me one sad song that wasn’t planned to be one.
All songs that tug at you are manipulative.
I’ve gotta disagree with the nomination for the Christmas Shoes song. The only reason it’s a “Christmas” song is because it mentions Christmas Eve.
The kid’s mom could have kicked off any time of year but I guess the songwriter was trying to write the next “Hvae Yourself a Merry Little Christmas” or something.
I keep hoping a new version will come out telling him “Look, she’s dead, no use in wasting your money on new shoes. Jesus doesn’t care what’s on her feet.”
Christmas in Prison by John Prine
It was christmas in prison
And the food was real good
We had turkey and pistols
Carved out of wood
And I dream of her always
Even when I don’t dream
Her name’s on my tongue
And her blood’s in my stream.
Chorus:
Wait awhile eternity
Old mother nature’s got nothing on me
Come to me
Run to me
Come to me, now
We’re rolling
My sweetheart
We’re flowing
By god!
<Middle verses cut for copyright reasons>
The search light in the big yard
Swings round with the gun
And spotlights the snowflakes
Like the dust in the sun
It’s christmas in prison
There’ll be music tonight
I’ll probably get homesick
I love you. goodnight.
<chorus>
Plenty of Christmas songs can make me feel maudlin or induce melancholy, but in terms of making me feel downright sad (and a little bit angry, for some reason) the only one that does it for me is Lennon’s Happy Xmas (War Is Over).
Well, using Tom Waits might be cheating, but… “Christmas Card From A Hooker In Minneapolis”
Then i seem to remember “Shouldn’t Have Given Him A Gun for Christmas” by Wall of Voodoo(Mexican Radio?), 1985 or so, can’t find the lyrics anywhere though.
Although it isn’t meant to be, “Silent Night” always struck me as sad and I f*cking hate that song.
I’m with Reeder on his nomination. That song is the saddest song period. I heard it for the first time two days ago (it’s about 2-3 years old, I’ve been told) and I had to pull the car over because I couldn’t see through the tears.
Probably the fact that my mom died of leukemia earlier this year and this is the first Christmas without her made the song much sadder than it was supposed to be. Any other time, under any other circumstances, and I’d probably be laughing my ass off at the hokiness.
I refuse to allow “Grandma Got Run Over” to be played in my presence. I will very emphatically change the channel or leave the room if I am subjected to that crap. I don’t hate many songs, but that one is top of the list.
The other day I heard Coldplay do “Have Yourself a Merry Little Christmas” and I just got so damn depressed. Ugh, I do not like this holiday season.