3 Depressing Holiday Songs

There are numerous places to go for happy holiday songs about snowmen, toys, and good cheer. But the holidays are often a depressing time of year for many, in part, because the songs and movies create such high expectations of perfection in our lives. So, to counter those expectations, here at Chimesfreedom we revisit three of the best depressing holiday songs, brought to you by Tom Waits, Joni Mitchell, and the Pogues. Because these songs lower one’s expectations, maybe they provide a source of joy for this time of year better than some of the syrupy happy songs.

The title of Tom Waits’s song, “Christmas Card from a Hooker in Minneapolis” sums it up. The song starts off with “Silent Night” to give the Christmas setting of the song, and then the “hooker” describes her life to Charley. She spins a tale about a husband and her memories, but at the end she confesses:

I don’t have a husband
He don’t play the trombone
And I need to borrow money
To pay this lawyer
And Charley, hey
I’ll be eligible for parole
Come Valentines day.

Then the singer goes back into “Silent Night,” evoking the hidden sadness that underlies that melancholy song, which is about the birth of a savior born into a fate of suffering. If you are not a Tom Waits fan, I realize his voice takes a little getting used to, but his gravely voice highlights the sadness of this tale.

From the first notes of the piano introduction to “The River,” on both Joni Mitchell’s original and Sarah McLachlan’s cover, you know you are in for a depressing song even if the initial notes are from the happiest of holiday songs, “Jingle Bells.” Like the two other songs here, “The River” begins by setting the scene for Christmas: “It’s coming on Christmas/ They’re cutting down trees / They’re putting up reindeer / And singing songs of joy and peace.”

But then, the song centers on memories of a failed relationship. “Now I’ve gone and lost the best baby / That I ever had /Oh I wish I had a river /I could skate away on.”

I prefer the Joni Mitchell version, but I could not find an actual video performance of the song (and what I did find was too full of depressing comments). So here is the McLachlan version of “The River,” which is also a good recording. But you are warned. It is depressing.

The Pogue’s “Fairytale of New York” (1987), featuring British singer Kirsty MacColl, is probably my favorite depressing holiday song. Despite the depressing lyrics, the joyous Irish tune lifts my spirits, in much the same way we find joy in other sad holiday stories like “Blue Christmas.” You know it is not a typical Christmas song from the first line: “It was Christmas Eve babe/In the drunk tank.” The singer then turns to memories of his “Queen of New York City” as he “can see a better time/When all our dreams come true.”

Then the band kicks in and the song features an exchange between a couple who are down on their luck.  They reflect on their hope in coming to America (“They got cars big as bars / They got rivers of gold”), tinged with dashed dreams (“But the wind goes right through you/It´s no place for the old”).

The couple fight and curse each other.   They exchange several barbs, referring to “an old slut on junk” with the holiday wish, “Happy Christmas your arse/ I pray God it’s our last.”  I have read a few different interpretations of what is going on in the song — whether it is a current relationship or a past relationship.  Despite the broken dreams of the song (“You took my dreams from me”), I like to think the song ends with a tiny sparkle of hope, “Can’t make it all alone/ I’ve built my dreams around you.”

Finally, we’re pulled back to the police station and the drunk tank,

The boys of the NYPD choir
Were singing “Galway Bay”
And the bells were ringing out
For Christmas day


Bonus Video Information: Recognize the police officer at the beginning of this video? He’s Matt Dillon.

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    5 thoughts on “3 Depressing Holiday Songs”

    1. so, like, I believe we both love Sprinsteen alot, right? but man-oh-man Tom Waits. He is living proof that sometimes the usual formula for awesome does not compute. Thanks so much for that video!

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