The Ten Most Depressing Christmas Songs Ever Recorded

The holidays are a bummer. At least Tom Waits knows it.

Tom Waits

By Jessica Gentile

Do you find the forced cheer of Christmas songs perversely depressing? Here are ten gloomy Christmas songs that may, in fact, cheer you up.

1) The Pogues and Kirsty MacColl, "Fairytale of New York"

Nothing says Christmas like youthful hopes and dreams crushed by alcoholism and drug addiction. Sung from the points of view of former lovers, the song features equal parts regret, melancholy and vitriol, whirling like raging snow. It's one of the most emotional holiday anthems of all time. "Happy Christmas your arse / I pray God it's our last." Amen.

2) Casiotone for the Painfully Alone, "Cold White Christmas"

Envision bleak twenty-something circumstances, then add a holiday. Dead-end job at a fast-food restaurant? Check. Complete absence of family and friends? Check. Moldy Minnesotan apartment and collect calls on Christmas? You bet. But, hey, at least you get to have beer for breakfast.

3) Okkervil River, "Listening to Otis Redding at Home During Christmas"

What better time to wax nostalgic for the one that got away than the holidays? Over plaintive chords, Will Sheff pines for snow days and Christmas cards from the girl who could have been more than just a friend. We've all got dreams to remember.

4) Sufjan Stevens, "Did I Make You Cry On Christmas Day? (Well, You Deserved It!)"

Trapped in an unhealthy and dysfunctional relationship? No better day to end it than Christmas. Well, that's what Sufjan claims to have done. True or not, only someone as adorable as he could get away with it. Coldhearted-ness rarely sounded so charming.

5) Aimee Mann, "I Was Thinking I Could Clean Up For Christmas"

Christmas is usually full of festive drinks — champagne, egg nog, etc. But it looks like Aimee Mann will stick with a Shirley Temple this year. This dour ode to sobriety sure puts a damper on the open bar.

6) Tom Waits, "Christmas Card From a Hooker in Minneapolis"

Granted, this Waits classic only references Christmas in its title. But the holiday context takes this tale about a destitute, pregnant prostitute from depressing to downright devastating. Throw in Waits' been-around-the-block-too-many-times rasp and you've got a weeper for the ages.

7) The Boy Least Likely To, "Blue Spruce Needles"

The Boy Least Likely To

It's easy to get overly sentimental during the holidays. The sight of a lone spruce needle swept under the couch from last year's Christmas tree is enough to bring tears to your eyes, especially if you're single — because the same time last year, you weren't.

8) John Denver, "Please Daddy (Don't Get Drunk this Christmas)"

Here's one Christmas song John Denver never sang with the Muppets (no one wants to see their mother cry, especially not Kermit). The title of this twangy tune just about says it all.

9) Prince, "Another Lonely Christmas"

It's hard to imagine someone as notoriously sexy as Prince spending Christmas alone, let alone multiple Christmases alone (as implied by the title), let alone "drink[ing] banana daiquiris 'til [he's] blind" in an effort to dull the pain. (Although that probably is what Prince would drink.) If he's not even immune to the holiday blues, then we're all doomed.

10) King Diamond, "No Presents for Christmas"

"No presents for Christmas" could probably serve as a shock-rock anthem for Ebenezer Scrooge, or the Grinch, or your stingy aunt. Hail Santa!

Commentarium (39 Comments)

Dec 13 10 - 1:41am

Joni Mitchell's "River" needs to be added to this list.

Dec 13 10 - 3:42am
Mr. Gentleman

As does Frightened Rabbit's "It's Christmas So We'll Stop". There's a little bit of hope in it, but like most Frightened Rabbit songs, it's hope in the face of crushing depression.

Dec 13 10 - 8:53am

"Grandma Got Run Over by a Reindeer" anyone?

Dec 13 10 - 9:25am

Where's The Ramones' 'Merry Xmas (I Don't Want to Fight Tonight)'? Surely that deserves a mention!

Dec 13 10 - 9:37am

Thank you so much for every music column you do, and in which you include the songs. I have found so much good music by reading your website, and since I am old and go to bed early and I don't date the music boys anymore, it has been hard to know where to score the good music. Your columns are greatly appreciated.

Dec 13 10 - 9:47am

No "Christmas Shoes"?

Dec 13 10 - 10:16am

No, because no one should ever listen to Christmas Shoes, even to mock it!

Dec 13 10 - 11:14am
Vinegar Bend

Well, I thank you for showing me some songs I didn't know, but "Fairytale of New York" is actually my favorite Christmas song, period, and I don't consider it depressing. I consider if heartwarming and moving. Maybe it's just me.

Dec 13 10 - 11:27am

I understand that a list like this could only really have one Sufjan Stevens song on it, but I would have nominated "That Was The Worst Christmas Ever" instead.

Dec 13 10 - 5:39pm

They missed Billy's Christmas... mid dies in Santa's arms on the way to heaven to visit hi dead father. Yikes's_Christmas_Wish_by_Red_Sovine

Dec 13 10 - 8:10pm

Sorry but none of these songs are anywhere near as depressing as Christmas Mourning by Type O Negative... not even close. What other Christmas song is complete with children crying and bottles smashing?

Dec 13 10 - 8:26pm

This song is really depressing.

Dec 13 10 - 8:30pm

"The Late Great Johnny Ace" Paul Simon

Dec 13 10 - 8:30pm

"The Late Great Johnny Ace" Paul Simon

Dec 13 10 - 9:36pm
Monica Morales

"Hard Candy Xmas" by Dolly Parton. Look it up!

Dec 13 10 - 10:16pm

"Brick" It's become forever associated with the Modern Rock stations for Xmas....

Dec 14 10 - 12:52pm

Oh! But what about The Waitresses' "Christmas Wrapping!?!?!?" Quite melancholy, especially in light of the idea that the singer committed suicide. I don't know if that's really true - I've never researched it - but it it is, then the song is doubly sad!

Dec 14 10 - 1:39pm

"Have Yourself A Merry Little Christmas"

Through the years
We all will be together,
If the Fates allow
Hang a shining star upon the highest bough.
And have yourself A merry little Christmas now.

Dec 14 10 - 8:15pm

"Christmas at Kmart" by Root Boy Slim absolutely needs to be here.

Dec 14 10 - 8:20pm
Root Boy on YouTube


Dec 15 10 - 3:26am

The Greatest Xmas Ever from The BIg Rock Show:

Dec 15 10 - 5:47am

Winter Song by Sara Bareilles & Ingrid Michaelson.
So. So. So. So. Sad.
The fucking chorus goes
"Is love alive?"

That and
The Heartache Can Wait by Brandi Carlile.

Awesome songs but so sad. Both off of The Hotel Cafe's compilation Christmas album.

I'm gonna go cry now....

Dec 15 10 - 6:01pm

What, no Red Sovine, for shame. Try the song, "What does Christmas Look like Daddy". Also check out the Fools "I'll spend Christmas with a bottle and a jukebox". You can't forget the wartime song, "Christmas in the Jungle". Freddy Fender, "If Christmas comes to your house, can I come over for a while".

Dec 16 10 - 2:16pm

"Blue Xmas (To Whom it May Concern"" by Miles Davis. Pretty clearly recorded at Columbia's insistence and under protest.

Dec 16 10 - 9:56pm

What about "Hang Myself From the Tree" by the Vandals? Most depressing one I've ever heard.

Dec 17 10 - 10:57pm

I made a great Christmas blues playlist on YouTube:

Dec 18 10 - 2:00am

Canceling Christmas, Michelle Featherstone
For those depressed from the loss of or missing a loved one this year

Dec 18 10 - 1:15pm
lil momma

"Same Old Lang Syne" by Dan Fogelberg

Dec 18 10 - 2:21pm
Bicycle Bill

Simon and Garfunkel did a version of "Silent Night" entitled "Seven O'Clock News/Silent Night". As the song played a voiceover began to be heard, reading the current news (actually the news of August 3, 1966 in that it mentions the death of comic Lenny Bruce). It gradually became louder and louder until the voiceover totally drowned out the song. It found as the final track of their "Parsley, Sage, Rosemary and Thyme" album.

Dec 18 10 - 4:12pm

There's the Father Christmas song by ELP- surprised it didn't make the list...

Dec 18 10 - 6:50pm

Speaking of Father Christmas, how did the Kinks' Father Christmas not make it?

Father Christmas, give us some money
We got no time for your silly toys
We'll beat you up if you don't hand it over
We want your bread so don't make us annoyed
Give all the toys to the little rich boys

Dec 18 10 - 6:54pm

BTW, Have Yourself a Merry Little Christmas is a little sad but check out the original lyrics:

Have yourself a merry little Christmas, it may be your last,
Next year we may all be living in the past

It was written for a musical in 1944 during WWII. Fun huh?

Dec 19 10 - 1:00am
Chris Hertzog

I think Randy Newman's Christmas in Cape Town might be just about the most depressing song, not so much for personal reasons but for the picture it paints of racial inequity

Dec 19 10 - 5:37am

364 days by murder city devils.

Dec 19 10 - 9:47am

Hang Myself from the Tree - The Vandals

Dec 19 10 - 2:07pm

"First Christmas" by Stan Rogers and "Christmas Croaker" by John Weldon deserve mention.

Dec 20 10 - 4:42pm

"I'll Be Home For Christmas" is actually horribly depressing once you know the meaning and history of the song. It is written from the point of view of a WW1 soldier who thought the war was going to be over fast once the US got involved. It was not. Hence the line; "If only in my dreams".

Dec 21 10 - 10:28pm

What about Cat Carol by Meryn Cadell?

Dec 06 11 - 11:57pm

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