25 Days of Holiday Songs 2025: “Merry Christmas From The Family” by Jill Sobule

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Man, this year’s countdown is really heavy on the obituaries. And what a shame that Jill Sobule is on that list at age 66; she certainly had more music in her.

This entry is really a choose your own adventure: if you’re feeling bummed out at the holidays, as so many of us do at times, try Sobule’s lovely original track “Christmas Is The Saddest Time of the Year,” in which the singer imagines all the lovely holiday moments that people who aren’t her get to have. “Actually, I think the song is more wistful than depressing,” she wrote on her website about the track in 2022. “Although, I did kind of shed a tear when I heard it today. I miss my parents.” Fair enough! It’s both.

Sobule also has a song if you’re feeling a bit more upbeat, a rollicking cover of Robert Earl Keen’s “Merry Christmas From The Family” she recorded in the 90s for a charity album. The family here is a wild bunch: “Mom got drunk and Dad got drunk at our Christmas party” is the opening line, and it’s downhill from there. (I especially love the reference to a can of bean dip: this year my family said goodbye to my wonderful, hilarious Uncle Jim, and he was the one who would always bring bean dip to our family Christmas parties before leading most of the caroling on his guitar.)

The song doesn’t at all hide that this is a dysfunctional night with an imperfect bunch, but maybe it’s better than being absent and wistful? To paraphrase Jill Sobule, I miss Jill Sobule.

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Brady Carlson
Brady Carlson
Brady Carlson is a writer and radio host from Madison, Wisconsin. more