For the Wallowers Among Us: The 15 Saddest Christmas Songs Ever

For the Wallowers Among Us: The 15 Saddest Christmas Songs Ever

The man in red's favorite sad girl compiled a playlist for your, uh, pleasure—because it ain't the holidays until somebody's crying!

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It’s well-documented that I thoroughly dislike Christmas. Fortunately, I’m in robust company. Don’t believe me? Just check the comments via that link.

Despite all of the reasons society tells us to like it—presents! parties! Papa Noël!—there’s even more to hate this holiday. And since the beginning of time, Christmas music—beyond its cheery chimes and stupid little bells—has told us exactly why. In short: depression, addiction, grief, poverty. Contrary to Andy Williams, it’s the sad-saddiest season of all.

As a martyr of the Claus, I have a playlist prepared for this time of year, one I reserve for staring wistfully out of the nearest window as I wait until January 1. And because I am nothing if not totally generous—moved by the Christmas spirit, if you will—I’ve ranked 15 of my favorites. But if you were expecting “Blue Christmas,” you’re not a real hater, you’re just glad tidings in Grinch clothing.

Sit back, relax, and let the music make you suffer an existential crisis.

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No. 15: “Please Come Home For Christmas,” Charles Brown

No. 15: “Please Come Home For Christmas,” Charles Brown

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Each time I happen to hear The Eagles’ version of “Please Come Home For Christmas,” my senses are permeated by the sights (empty stools, Block O calf tattoos) and smells (cigarette smoke, stale popcorn) of a Midwestern dive bar. But when I hear the original, written and performed by blues singer and pianist Charles Brown? I can actually feel the glumness I imagine a person might experience while pleading with someone they love to just stick around for Christmas.

Most ho-ho-hold me lyric: “So won’t you tell me you’ll never more roam/Christmas and New Year’s will find you home/There’ll be no more sorrow, no grief and pain/And I’ll be happy, happy once again.”

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No. 14: “Christmas Makes Me Cry,” Kacey Musgraves

No. 14: “Christmas Makes Me Cry,” Kacey Musgraves

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One thing about me? I’m never not grappling with intrusive thoughts about my parents’ demise. Fortunately, I’ve learned how to keep them out in the cold 11 months out 12, but there’s something about December that weakens my resolve just enough to invite them in for a cup of cocoa. “Stay a while, old friends,” I say, allowing my mind to conjure a ghastly image of a year—hopefully in the distant future—in which my mom and dad are no longer here, and, in an effort to cope with that reality, I’ve set a nativity scene on fire somewhere with my Marlboro light.

Anyway! Kacey Musgraves gifted lunatics like me this gem on her first Christmas album, A Very Kacey Christmas, and it begins with a succinct voiceover explaining its existence on an otherwise optimistic album: “It feels like we are supposed to be happy during the holidays. But sometimes they just make you really sad.”

Most ho-ho-hold me lyric: “It seems like everybody else is having fun/I wonder if I’m the only one/Whose broken heart still has broken parts just wrapped in pretty paper/And it’s always sad seeing mom and dad getting a little grayer”

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No. 13: “Same Auld Lang Syne,” Dan Fogelberg

No. 13: “Same Auld Lang Syne,” Dan Fogelberg

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Picture it: You’re holed up at your parents’ home on Christmas Eve and desperate to get just tipsy enough to tolerate another question about what is you do exactly (skip that part if you’re not a journalist) and pass out in your childhood bedroom. Only you’re out of eggnog. So, off you go to the local grocery store. As you ponder which brand of milk punch to purchase, your sleeve is grazed by a hand belonging to an ex you haven’t seen since you broke up in high school. They’re out buying something to bring home to mom and dad too. Serendipity! Because it’s actually a pleasant surprise, you decide to catch up and, inevitably, wind up splitting a six-pack in their car. “Just like old times,” you might think—except for the fact that it isn’t. The only thing you have left in common are mere memories.

“Same Auld Lang Syne” is so achingly specific that it should arrive as no surprise that Dan Fogelberg wrote it about a very real encounter with his ex girlfriend on Christmas Eve. Before he passed away in 2007, Fogelberg divulged that though all of the lyrics are true, he “didn’t tell the whole story.” Somehow that information makes this song all the more wretched.

Most ho-ho-hold me lyric: “We drank a toast to innocence/We drank a toast to now/And tried to reach beyond the emptiness/But neither one knew how”

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No. 12: “Someday at Christmas,” Stevie Wonder

No. 12: “Someday at Christmas,” Stevie Wonder

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There’s a chance you might detect a trace of hope in “Someday at Christmas.” If so, you’re wrong. Why am I so sure? The song spends just two verses listing all the things that are wrong with the world, only to remind us in the refrain that we’ll probably never live to see even some of said things end (war, poverty). Sick!

Most ho-ho-hold me lyric: “When we have found what life’s really worth/There’ll be peace on earth”

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No. 11: “Silent Night/7 O’Clock News,” Simon and Garfunkel

No. 11: “Silent Night/7 O’Clock News,” Simon and Garfunkel

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Homicide! Anti-protest arrests! War! This little ditty has it all! Yes, folks, it’s literally just Simon and Garfunkel softly crooning “Silent Night” whilst bleak news bulletins are read.

Fun fact: In 2019, Phoebe Bridgers, Fiona Apple, and The National’s Matt Berninger re-recorded this song using modern news items. Ex: “The Supreme Court is reviewing a Louisiana law that would effectively end women’s access to abortion. The law, seen as a first step by evangelical conservatives toward the possible reversing of Roe v. Wade, flies in the face of public opinion.” Unsurprisingly, this is not the last Phoebe Bridgers re-recording of a depressing Christmas song on this list.

Most ho-ho-hold me lyric: “President Johnson originally proposed an outright ban covering discrimination/by everyone for every type of housing but it had no chance from the start/and everyone in Congress knew it”

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No. 10: “Another Lonely Christmas,” Prince

No. 10: “Another Lonely Christmas,” Prince

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Only Prince can write a Christmas song that’s both sad and sensual. “Remember the time we swam naked in your father’s pool?” he reminisces on the second verse. Of course, the question isn’t intended for us, the listeners. It’s for a former lover. But before one can fully wonder how or why someone would dare leave the sexiest man ever to hail from Minnesota, he cuts right to it: She died.

Most ho-ho-hold me lyric: “Your father said it was pneumonia/Your mother said it was strep/But the doctor said you were dead and I/I say it’s senseless”

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No. 9: “Merry Christmas, Darling,” The Carpenters

No. 9: “Merry Christmas, Darling,” The Carpenters

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I know what you’re thinking: Singing about missing someone? On a Christmas song? Groundbreaking. It’s true. This cursed holiday boasts a hundred songs about yearning for a special someone’s presence. However, only a few are bolstered by the truly haunting vocals of one Karen Carpenter. Sure, it’s another song about trying to make the best of the holiday when the one you love isn’t with you. But it’s impossible to conclude if the subject of Carpenter’s sonic sentiments is alive and just forced to celebrate elsewhere or, well, no longer of this earthly plane. Some morbidness with your melancholia?

Most ho-ho-hold me lyric: “I’ve just one wish on this Christmas Eve/I wish I were with you”

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No. 8: “The Little Boy That Santa Claus Forgot,” Nat King Cole

No. 8: “The Little Boy That Santa Claus Forgot,” Nat King Cole

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Is there anything more miserable than missing someone on Christmas? Yes. Being poor on Christmas—more specifically, being a poor child on Christmas. Everyone’s fond of Nat King Cole’s rendition of “The Christmas Song,” but “The Little Boy That Santa Claus Forgot” is often unremembered. Why? Because it’s gut-wrenching. A fatherless little boy forced to watch all of the other kids delight in their shiny new toys? He didn’t want a lot...just some soldiers and a drum. But because life is cruel and Santa Claus is notably not a socialist, last year’s broken toys will have to do.

Most ho-ho-hold me lyric: “I’ll tell you of a little boy that lives across the way/This little fella’s Christmas is just another day”

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No. 7: “The Christmas Shoes,” NewSong

No. 7: “The Christmas Shoes,” NewSong

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What? You thought this list would omit the fucking shoes song? I’m not a monster. Everyone knows this one, therefore I’m not justifying its inclusion. But if you’re wondering why a song about a child saving his money to purchase a pair of shoes for his ailing mother on Christmas isn’t No. 1, blame the corny visuals.

Most ho-ho-hold me lyric: “He counted pennies for what seemed like years/Then the cashier said, ‘son, there’s not enough here’”

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No. 6 - “Christmas Will Break Your Heart,” LCD Soundsystem

No. 6 - “Christmas Will Break Your Heart,” LCD Soundsystem

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“Christmas Can Break Your Heart” is what all sad Christmas songs should be. It’s not sickly sentimental, nor is it reliant on string-heavy accompaniments and distracting nostalgia. It’s just sad dudes being sad—and imagery that lands like your nihilist cousin’s jokes at the dinner table.

Lore (aka Twitter) has it that the original iteration of the song had “75 lines” of lyrics. “We’ve knocked [it] down to eight to keep the suicide rate in check,” a statement from the band noted upon the track’s release. Thanks, guys!

Most ho-ho-hold me lyric: “Christmas can wreck your head/Like some listless awkward sex/So you refuse to leave your bed/Get depressed when no one checks”

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No. 5: “Hard Candy Christmas,” Dolly Parton

No. 5: “Hard Candy Christmas,” Dolly Parton

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If you happened to read this essay, you’re already aware that I’ve survived the last five or six Christmases due largely in part to “Hard Candy Christmas.” Dolly Parton didn’t write this song, but right from the opening chord, it’s hers. “Hard Candy Christmas” spends four verses pondering what one is to do to keep those pesky holiday blues at bay: Stay sober and practice productivity? Get drunk and stay awake until dawn? This is more than a song, my friends. It’s representation for someone plagued by a certain restlessness at the end of the year, the kind so all-consuming it convinces you that you do, in fact, have the face for bangs or the idea for the next great podcast.

Most ho-ho-hold me lyric: “Maybe I’ll sleep real late/Maybe I’ll lose some weight/Maybe I’ll clear my junk/Maybe I’ll just get drunk on apple wine”

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No. 4: “If We Make It Through December,” Phoebe Bridgers

No. 4: “If We Make It Through December,” Phoebe Bridgers

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Merle Haggard wrote and performed “If We Make It Through December” as a sort of reassuring little tune, sung from the perspective of a father who’s been laid off just before the holidays. “If we make it through December, we’ll be fine,” he tells himself, imagining sunnier skies next year. When Phoebe Bridgers sings it? There’s no promise, only the grave reality that a father can’t afford to give his daughter a Christmas because The Man™ wrung him out like soiled dishrag and discarded of him. How soon is too soon to explain labor exploitation to a kid?

Most ho-ho-hold me lyric: “I don’t mean to hate December/It’s meant to be the happy time of year/But my little girl don’t understand/Why daddy can’t afford no Christmas here”

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No. 3: “Have Yourself A Merry Little Christmas,” Judy Garland

No. 3: “Have Yourself A Merry Little Christmas,” Judy Garland

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Did you know, the original lyrics of “Have Yourself A Merry Little Christmas” were so dismal that Judy Garland, the leading lady of Meet Me in St. Louis—the film in which the song first appeared—refused to sing them? That’s right, upon an early reading of the script, the Hollywood darling pulled rank and the studio was forced to deliver a rewrite. The lyrics were, as follows: “Have yourself a merry little Christmas/It may be your last/Next year we may all be living in the past.” While the amended lyrics are—I guess—a bit more cheery, I’ll never hear the song the same way.

Most ho-ho-hold me lyric: “Next year all our troubles will be miles away”

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No. 2: “So Much Wine,” The Handsome Family

No. 2: “So Much Wine,” The Handsome Family

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It’s not a particularly revolutionary message, drinking in the hopes of one day being full enough not to notice how very empty you are. Alcoholism and its affects on anyone and everyone within its warpath are at the heart of this 2000 track, and the acute helplessness of the singer—actively bearing witness to a loved one grappling with addiction at the holidays—will most certainly break yours.

Most ho-ho-hold me lyric: “Listen to me, butterfly, there’s only so much wine/That you can drink in one life/And it will never be enough/To save you from the bottom of your glass”

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No. 1: River, Joni Mitchell

No. 1: River, Joni Mitchell

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Everyone who’s anyone—from James Taylor to Lea Michele—has covered “River,” but no one will ever sing it quite like Joni Mitchell. Not even me...alone in the car...sitting in my parents’ driveway. Every plaintive wail drips with self-indulgence like melting icicles clotted along a gutter. But perhaps the most admirable thing about Mitchell is she’s always conscious of her own navel-gazing.

Indeed, there’s a distinct loneliness that accompanies facing up to the fact that you’ve fucked up. In this case, Mitchell’s owning that she’s just caused someone she loves profound heartbreak. But realizing you can never fully flee the harm you’ve inflicted, regardless of how far you try and skate away? Well, that’s just torture.

Most ho-ho-hold me lyric: “I’m so hard to handle/I’m selfish and I’m sad/Now I’ve gone and lost the best baby/That I ever had”

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