The Saddest Christmas Songs in the World

piano-ornamentI promised more Christmas playlists from my extensive Christmas music collection. As I’ve told you before, my Christmas music collection is broad and deep, spanning nearly every musical genre — although I am seriously considering trashing that Heavy Metal Christmas album. I’ve made a number of playlists through the years, many of them compiled for your easy reference here. You may not thank me for this latest one. But someone’s got to do it. Yes, sometimes you just want to wallow in self-pity and it seems to work best when everyone around you is having a Holly Jolly Christmas. So without further ado, here is my playlist of the Christmas music most likely to make you want to drown your sorrows in a tub of eggnog. Hey, have a Happy Holiday!

1. Song for a Winter’s Night, Sarah McLachlan. This one has it all — an almost empty glass and a missing loved one. Then it veers off into a truly Victorian level of misery with a lamp almost exhausted, a fire dying out, smoke rising in the shadows. I can only assume Sarah’s singing this from some snowbound woodsman’s cottage in Scotland. Or maybe a tenement in 1880s London. Or maybe she’s realized that an electric furnace going into power-saving mode, an LED lamp and the distant glow of a laptop just doesn’t bring the pathos like the accoutrements of an earlier age.

2. Same Old Lang Syne, Dan Fogelberg. Dan one-ups Sarah by managing to keep things maudlin while staying in the 20th Century. HIs song charts two former lovers meeting on Christmas Eve in a record store, drinking a beer in his car and reminiscing about their not too happy current lives. Then the snow turns to rain. Misery perfection.

I bet you think this list is going to include the Pogues’ Fairytale of New York or that Christian group’s New Shoes. Sorry, neither one makes the cut for the simple reason that they try too hard. Yes, the former has a drunk incarcerated man thinking about past failed loves, but that’s a bit like a Country singer desperately trying to work trains, Momma and drinking into a single song. And the latter? I utterly reject the premise that this poor kid thinks Jesus won’t find his dying mother properly dressed for Heaven without new shoes. No, the songs that make my list have to be truly sad without straining.

Did terriers eat your presents? Go ahead, listen to these sad Christmas songs and wallow.

Did terriers eat your presents? Go ahead, listen to these sad Christmas songs and wallow.

3. Have Yourself a Merry Little Christmas, Judy Garland. This one will break your heart — but only if you listen to the original Judy Garland version as sung in Meet Me In St. Louis. What makes it such a winner in the Sadness Sweepstakes is that it purports to be a happy song — but is really a mediation on an uncertain future. You can up the crying quotient by finding one of Judy’s later Christmas albums released a few years before her death. That’s the time she was constantly fighting bankruptcy and desperately doing punishing concert tours to keep the wolf from the door. On her last Christmas album, she delivers as only Judy can when she gets to this song.

4. River, Joni Mitchell. “It’s comin’ on Christmas/They’re cutting down trees/They’re putting up reindeer/And singing songs of joy and peace.” But all Joni Mitchell wants to do is find the world’s largest frozen river and skate away on it. Why? Because she drove away the man she suspects may be the love of her life. Simple. Direct. Devastating.

5. If We Make It Through December, Merle Haggard. The Great Depression, the Dust Bowl and the Okie Migration that brought his family to the Tulare dust are the defining moments in Merle’s life. No matter what song he sings, that hardscrabble life and the several jail stints are always lurking in the background. This song is no exception as a family looks toward Christmas as the make it or break it point.

6. Sweet Little Jesus Boy, Mahalia Jackson. You could also choose the versions by Kathleen Battle, Natalie Cole or Odetta. This sounds like such a beautiful simple Spiritual, I imagined it dated back from the Antebellum South. Nope, it was written by a White Louisiana composer in 1934. Apparently he was surrounded by African American neighbors and wrote in that genre. Doesn’t matter. Instead of Hallelujahs and fanfare, this song reflects on the humble birth of Christ and the sad state of human nature sometimes: “World treats you mean, Lord/Treats me mean, too/But that’s how things done down here/We didn’t know it was You.”

7. The Christmas Blues, Dean Martin. For crying in your Martini, you just can’t beat Dean. Especially since there is always an element in a sad Dean song that says he’s going to pick himself up, dust himself off and carry on. Right after another one for the road.

May all your days be merry
Your seasons full of cheer
But ’til it’s January
I’ll just go and disappear
Oh Santa may have brought you some stars for your shoes
But Santa only brought me the blues
Those brightly packaged tinsel covered Christmas blues

8. Please Come Home for Christmas, Charles Brown. You can skip this whole list and just buy Charles Brown’s great Christmas Blues album. It’s one of my go-to Christmas albums that even my Grinchiest friends love, probably because of Brown’s Blues tinged R&B stylings. If you want to get out of the tinsel and the wrapping, follow Charles Brown into a smokey, virtual Blues bar somewhere between Chicago and East Texas where every Christmas is accompanied by a shot of Rye.

9. Santa Claus Go Straight to the Ghetto, James Brown. Not the jokey song you’d think it might be. James Brown has marching orders for Santa: Fill every stocking you see, and don’t forget any kid. With the accompanying driving funky guitar, we think Santa will obey. And maybe in our misery, we should reflect on others who might have it worse.

10. Auld Lang Syne, Susan Boyle. Yes, THAT Susan Boyle, the frumpy old maid who was the break-out opera star of one of those TV talent shows. Bing, Dean and Frank always drive me crazy when they sing this song with an upbeat tempo. Robert Burns wrote the poem almost as an elegy about not forgetting old times and friends even when the good times have ended and the friends are no longer with us. Susan Boyle, who is Scottish, knows exactly what Burns meant. Until she won Britain’s Got Talent, she lived a quiet life of interrupted dreams — learning disabilities, ill parents, penny pinching. Now she’s internationally known and worth something like 22 million pounds. But she sure knows how to wring every heartache out of this one.

So there you have it. Break out the vodka. Shed some tears and wad up the tinsel. Then, after a suitable period of wallowing, get up off your duff and have a wonderful holiday season!


It’s okay to be sad at Christmas. Especially if you are a bad little terrier and didn’t get nearly enough cookies and chew toys.

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Author: Lisa

Although I'd like to think of myself as a rootin', tootin', wine-makin' cowgirl, I currently only live in Sonoma part-time. Mostly I'm on freeways between San Jose, San Francisco and Sonoma. With two yapping terriers in crates behind me. We try to enjoy all three places and points in between. Which will explain why my post subjects are all over the map.

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  1. That is definitely a sad one. From a poem by Longfellow, written after his son had secretly enlisted in the Civil War then been seriously injured. But I like the Elvis version.

  2. Agreed about “Bells.” lovely, poignant words and melody. During our neighborhood singalong last night, we realized how many of the lyrics in the “old chestnuts” allude to innocent children; impossibly sad this year. How about something cheerier: Modern Mandolin Orchestra’s “Nutcracker,” John Fahey’s Christmas album (a combo of happy, sad and, well, Fahey) and Charlie Parker’s perky “White Christmas” from Savoy. For a little post-Christmas Russian emotion: Tchaikovsky’s evocative Symphony #1, “Winter Dreams.”
    And, there is mothing sadder than a terrier who doesn’t get what he thinks he deserves. Those big, sad brown eyes wiith the built-in eyeliner :-(
    Thank you for sharing your splendid playlist. I think it could crash my iPod, and I may not get through it all until next Christmas!

  3. Most of my other playlists are much cheerier. But I’ve been wanting to do this one for awhile. Didn’t want it to be tragic. Just a wallow in self-pity. This is the playlist you listen to when you overspike your eggnog and feel sorry for yourself because you got another ugly sweater.

  4. Love, love, love the Judy Garland and Charles Brown! The CB is my all-time favorite version of that song! What a great playlist! 2011 was our first Christmas with Jameson in our house. He was mostly good about the tree, until I foolishly put the boxed and wrapped cashmere sweater I’d bought my brother-in-law under it. We caught poor Jamie trying to free the goat he smelled in the box. This year, he did better, and Santa brought him a nice bag of home-made pumpkin-peanut butter treats and a Rope Penguin (which Britta killed).

    I would add the McGarrigles’ version of “Rebel Jesus” to this list. Jackson Browne’s classic reminder of how we all fail to get the message of Christmas done by one of the best vocal groups either, abetted by the Pixies.

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  6. I’d have to include “Fairytale of New York” by the Pogues & Kirsty MacColl, “Cold White Christmas” by Casiotone for the Painfully Alone (my personal fave), “Christmas Journey” by Wayne Newton (hard to find but worth it), “Calling on Mary” by Aimee Mann, and of course, the brilliant Jimmy Webb penned (when he was about 20) the cult classic “Whatever Happened to Christmas” which was sung by both Aimee Mann and Frank Sinatra. Merry (and Happy) Christmas!

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