Top 10 Depressing Holiday Songs

The previous post on Three Depressing Holiday Songs got us started thinking about the best depressing holiday songs.  So, this post features Chimesfreedom’s Top Ten Depressing Holiday Songs.  We selected these top 10 based upon three categories. Points were given for (1) deep depression and sadness; (2) quality of song; and (3) familiarity of the song.

(1) Fairytale of New York” – The Pogues: Scored high in all three categories.  Discussed in previous post in more detail, but all you really need is the opening line of the song: “It was Christmas Eve, babe,/ In the drunk tank.” Score:  97 points.

(2) “Blue Christmas” – Elvis Presley, etc.: Gets high on the list because very familiar and a good song, but the music is not that sad. For more, we discussed the story behind Elvis Presley’s most famous performance of the song. Score:  93 points.

(3) “The River– Joni Mitchell (and covers): Received most of its points from the deep depression category with both depressing lyrics and music.  Discussed in previous post in more detail.  Score:  91 points.

(4) Pretty Paper” – Roy Orbison:  The lyrics to “Pretty Paper” are a little vague, but a guy is alone on the sidewalk hoping “that you won’t pass him by.” “You’re in a hurry” so you leave him there crying as people laugh in the distance. You suck. Anyway, it has Roy Orbison’s voice, which automatically puts it high on the sounding-sad scale.  If he sang “Jingle Bells” it would make this list. Score:  89 points.

(5) Do They Know It Is Christmas?” – Band Aid: Very famous and depressing: “Where nothing ever grows/ No rain or rivers flow.” And then there is Bono wailing, “Tonight thank God it’s them instead of yooooooooooooo!”  “Do They Know It’s Christmas” would be higher on the list, but by the end we are happily singing “Feed the world” and letting people know it is Christmas Time whether they want to know it or not.   But while it did raise money for a good cause, the song has an extra tinge of sadness because it also reminds us that we did not find a solution to hunger in the 26 years since the song was released.  We mock, but we love the song. Just avoid the two remakes from 1989 and 2004. Score:  88 points. Trivia Question: Who sings the Bono part in the 2004 Band Aid 20 remake?

(5) “Christmas in Prison” – John Prine. We like John Prine and the quality of “Christmas in Prison,” so we are putting it above some other songs even though you may never have heard it. Plus, you got prison: “The search light in the big yard / Swings round with the gun / And spotlights the snowflakes / Like the dust in the sun.” Check it out below.  Score:  84 points.

(7) “Christmas Card from a Hooker in Minneapolis” – Tom Waits: Scored high on the depression scale, but not a song for many repeated listenings and not as famous as some of the above songs.  Discussed in previous post in more detail.  Score:  79 points.

(8) I’ll Be Home for Christmas” and “White Christmas” (tie) – Bing Crosby and others: Familiarity got these two into the top ten. The music sounds depressing, but the person is missing one Christmas and seems to still have family they will see again. For “I’ll Be Home For Christmas,” the guy who wrote the lyrics was thinking of a homesick kid in college.  C’mon kid, there are people starving in Africa.  At least “White Christmas” gets bonus sad points from its popularity being connected to WWII soldiers missing home.  These songs are sad, but not hooker-in-prison sad.   Score:  78 points.

(9) “Billy’s Christmas Wish” – Red Sovine: “Billy’s Christmas Wish” may not be as well known as the other songs here, but the song is unbeatable on the depression scale so it makes the list on that alone. Consider: (1) the little boy’s father is in prison for shooting the mother’s boyfriend; (2) the mother works in a bar and lives with an abusive “Mr. Brown;” and (3) then the little boy dies on Santa’s lap at the end. Seriously, that is the song. And then Santa has the nerve to tell us not to be sad because the boy wanted to live with God so “now everything’s alright.” That makes us think that Santa killed Billy.  Score:  72 points.

(10) “The Rebel Jesus” – Jackson Browne. The Top Ten List must have room for a song that gets to the heart of Christmas and how the spirit of it gets corrupted, calling us out for our hypocrisy. Everyone may not know this song, but it is a beautiful song of the season. Score: 68 points.

Well we guard our world with locks and guns,
And we guard our fine possessions.
And once a year when Christmas comes,
We give to our relations.
And perhaps we give a little to the poor,
If the generosity should seize us.
But if any one of us should interfere
In the business of why there are poor,
They get the same as the rebel Jesus

I went shopping today and bought a present for my mom, and then I sang along to “Do They Know It’s Christmas” without doing anything about the poor.  I am a worthless human being.  Thanks Jackson Browne for making me feel like crap.   If you need to feel a little better, you may use the charity of your choice or use these links for CARE, Oxfam, or UNICEF.

Honorable Mention: “Please Daddy Don’t Get Drunk This Christmas” – John Denver: You do not hear this one a lot, and I just discovered Alan Jackson covered the song. The song is sad with the kid worrying whether daddy will be drunk again this Christmas, but it is played as a clap-along song so not as depressing as it could be. Plus, the kid has it good compared to Billy in the Red Sovine song.  Score:  54 points.

Bonus Recent Excellent Sad Holiday Song: Mike Ireland and Holler‘s “Christmas Past.” I found this song last year and really like it, and when you hear it, the melody sounds like a song you have heard many times before. The song features various memories floating by and ends with: “The only company I keep exists in memories / Leaving me alone on Christmas Day.” Sad, but a pretty song.

Bonus Links: In preparing this post, I did some googling and saw that others had compiled similar lists that you may see and compare here, here, here, and here.

What’s your favorite depressing holiday song? Post a comment.

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    9 thoughts on “Top 10 Depressing Holiday Songs”

    1. You missed that awful pop-country song about a kid who wants to buy his dying mother some red shoes. Depressing not so much for the lyrics, but for the image of countless drunken losers crying in strip mall parking lots listening to the song.

    2. How did I miss “Christmas Shoes” by NewSong? It was made into a NY Times Bestselling Book and then a TV movie seen by “nearly 17 million people” according to Wikipedia. But it still does not make The Top Ten Depressing Holiday Songs. As you note, it is not really a great song, and everyone is happy at the end: the kid gets the shoes and the singer feels better because he helped a kid buy the shoes for his sick mom. It is like “The Christmas Carol,” except the Scrooge narrator (“Trying to buy that last gift or two/Not really in the Christmas mood”) does not have to go through the nightmares to enjoy Christmas again when he realizes, “God had sent that little boy to remind me what Christmas is all about.” Too bad the little boy might lose his mother, but the narrator believed it was worthwhile because it helped him enjoy the rest of his Christmas shopping.

      There is video of the song made by someone in film school that has been watched almost two million times:

    3. oh I guess as long as the narrator feels better about shopping it’s okay. Much like the a**holes listening in the car who aren’t even buying shoes for cancer-ridden dying women. . . It’s not a depressing song at all. Just don’t view it from the soon-to-be-orphan son’s point of view.
      Seriously, I liked the John Prine song a lot. So thx.

    4. On Twitter, someone responded to the previous Chimesfreedom post with the sad holiday song “7 o’clock News/Silent Night” (1966) by Simon & Garfunkel. The song starts out with the two singing “Silent Night” and then a simulated newscast of the news from Aug. 3, 1966 starts playing over the song. (Thanks to border_rebel.) It’s a nice effect, making a sad-sounding song even sadder.

    5. Very interesting list. I do have one correction and that is about your characterization of the history of the subject of “White Christmas”. Irving Berlin wrote the song in 1940 prior to US entry into WWII. Additionally, an often deleted verse refers to the warm weather of Beverly Hills LA, making the song much more about longing for a classic impression of the season rather than about soldiers overseas. See Wikipedia for details.

      1. Thanks for the comment. You’re correct that even though there are different stories about the writing of “White Christmas,” its connection to World War II had to do with its release and popularity during that time (so I’ve updated to post to reflect that). Take care.

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