Sobbin’ Around the Christmas Tree: The 100 Greatest Sad Holiday Songs

joni mitchell merle haggard judy garland sad christmas songs list 100 holiday music

Is Christmas really the saddest day of the year? There’s a whole history of holiday music that explores what it’s like to be down-and-out during the season. Are you mourning absent family members? Resenting the ex who ghosted you for Xmas? Or just wondering why, in 2024, everybody else is celebrating the holly instead of the melancholy? Take heart: We’ve got the unmerry miserabilists for you.

Sad Christmas music is practically a genre unto itself. One good starting point, if you can find it, is Rhino’s long-out-of-print “Bummed Out Christmas” CD. But we’ve got our own playlist of classics and obscurities to help you turn that fake holiday smile upside down.

Most performers sing the version with the happy, rewritten lyrics that Frank Sinatra asked songwriter Hugh Martin to come up with in the ‘50s to “jolly it up a little.” But the superior version is the more ominous and morose “have to muddle through somehow” original, as sung in the ‘40s by Judy Garland. The tune originated in “Meet Me in St. Louis,” in which Garland sings it to cheer up her sister, Margaret O’Brien, as they prepare to move away from the home they hold dear after the holidays. The consoling goes so well that the little girl breaks down in sobs and proceeds to immediately murder a snowman.

Mitchell’s Christmas-set ballad was just another “Blue” album track for decades, then suddenly became the number that everybody covers on their holiday albums as their token downbeat number. Notably, while most other sad seasonal songs are about getting dumped for the holidays, Mitchell is guilt-racked because she made a dude cry. Joni is one sad Christmas boss.

Haggard is trying to keep the family’s spirits up, probably in vain, in this classic slab of Christmas neo-realism. The kids’ gifts may not be so great this year, because Daddy “got laid off down at the factory” — but he suggests it’ll be better next year if they move to California. Or maybe not? Substitute “got laid off by a major media company” and you’ve got an anthem for Hollywood in 2024.

Though Crosby and other interpreters are rarely accused of playing a trick on anyone, this is a stellar example of the “gotcha” song — seeming to promise home and hearth, until we get to that “only in my dreams” line, and realize the singer is probably stuck on a WWII battlefield. (Or somewhere else irretrievable, if we’re not in the 1940s.)

The weather outside is frightful, and the belief in humanity runs just as cold, in the brothers’ soaring but remarkably despondent ballad. A forlorn hitchhiker wards off frostbite on a snowy roadside as cars speed by … even as he admits that if he had a family waiting, he’d pass himself up too.

When the Waitresses go out to the A&P on Christmas Eve in “Christmas Wrapping,” a meet-cute ensues. But when Fogelberg goes out for last-minute groceries, he runs into an ex, and they crack open a six-pack in his car as she details her loveless marriage. Then the snow turns to rain, because of course it does.

Accompanied by the E Street Band on this unofficial sequel to “Christmas (Baby Please Come Home),” she sings out for all the souls who don’t have a baby to even long for. But it’s always OK not to have anyone to cuddle up with at Christmas when you’ve got Darlene Love’s voice to keep you warm.