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!

previous arrow next arrow
Photo: James Leynse (Getty Images)

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.

Inline Feedbacks
View all comments
Share Tweet Submit Pin