For many among us, all the joy and good (and candy!) that accompanies the holiday season also comes with stress, exhaustion and sadness. While Christmastime magnifies the best feelings, it can also magnify the worst; Charlie Brown said it best: “I just don’t understand Christmas, I guess. I like getting presents and sending Christmas cards and decorating trees and all that, but I’m still not happy. I always end up feeling depressed.”
No one understands Christmas, Charlie Brown. The holiday season is a confusing emotional roller coaster, and sometimes the best medicine is grabbing your record player, some fantastic and sad tunes and just crying it out. So with that, here’s a list of the saddest holiday songs (along with a Spotify playlist at the bottom of this post) to get you through those times when you just want to let your #FEELINGS win for a minute, because there’s no shame in indulging in a good Christmas cry.
Bright Eyes, “Have Yourself a Merry Little Christmas”
Originally performed by Judy Garland in 1944, this song has always felt haunted, and the World’s Saddest Band really evokes and embraces those morose vibes on this version, which whimpers along with delicate piano and weeping strings. It’s the song you put on at the Christmas party when you want everyone to leave. (But be warned: Friends will probably send subsequent well-intentioned “Are you OK?” texts.)
Murder City Devils, “364 Days”
I mean, what more do you need from a sad Christmas song? It’s a drunken, sloppy love letter to Santa Claus, lamenting the 364 lonely days the man has to kill before next Christmas, and it’s wonderful.
Prince, “Another Lonely Christmas”
Two minutes into The Purple One’s 1984 “I Would Die 4 U” B-side, “Another Lonely Christmas,” it might sound like the cucumber-cool rock star is pining for a lost love, but as the narrator keeps downing banana daiquiris, getting increasingly drunk while recalling cherished Christmas memories, we discover the love of his life is actually DEAD. Of pneumonia? Stress maybe? Who knows. Oof.
Darlene Love, “Christmas (Baby Please Come Home)”
It’s easy to forget this song is such a heart-breaker when the instrumentation (especially the sax solo!) feels so triumphant and anthemic, but crooner Darlene Love sounds 100 percent heartbroken as she cries out, “If there was a way, I’d hold back this tear / But it’s Christmas Day / Baby please come home!” If you need a less bright-and-shiny version of this tune, check out Death Cab for Cutie’s totally defeated take on it — it’s every bit as sappy and sad, as you’d expect from a band with such deep roots in the gray Pacific Northwest.
Tom Waits, “Christmas Card from a Hooker in Minneapolis”
At first this song gives us hope — a woman, while writing a letter to a man named Charlie, says she might be happy for the first time in her life. She’s off drugs; she’s got a good man who takes her dancing; and she playfully imagines what she’d do if she still had all the money she spent on dope. Then, in a way that only Tom Waits can, with his heartbreaking, gravelly voice, the singer squashes that hope (and our hearts) with the sad truth: Her good fortunes are only just fantasies and she’s actually in prison.
Chumped, “December is the Longest Month”
Technically, this is not a Christmas song — it’s actually the sweetly emotional opening track of Chumped’s great new power-pop album, Teenage Retirement — but the tune’s truthful lyrics hit the hardest right now, when there’s still more than a week left of December. And because the holiday season has drained all that was left in the emotional reserves, even a week can feel like a lifetime. The hesitant pep talk that singer Anika Pyle delivers right before the chorus — “This is not that hard / You’re doing great, you’re doing fine / Just wake up” — feels especially poignant. I want to sew those words onto a pillow and hug it to sleep every night.
More songs that might make you drop a tear in your eggnog: Ray Charles’ “That Spirit of Christmas,” Chris Farren’s “I’m Not Ready for Christmas,” Harvey Danger’s “Sometimes You Have To Work on Christmas (Sometimes),” The Pretenders’ “2000 Miles,” Weezer’s “The Christmas Song” and Charles Brown’s “Please Come Home for Christmas.”
Listen to all these songs (and more) in this tragically sad playlist:
