Mass. native Josh Gondelman joins the tour again this year.
By Nick A. Zaino III Globe correspondent,Updated November 6, 2025, 6:00 a.m.
Silly and earnest never mingle quite so freely as they do during the Christmas season. And for more than a decade, the Aimee Mann & Ted Leo Christmas Show has embraced that mix, featuring cozy renditions of favorites like “The Christmas Song” and “I’ll Be Home for Christmas” along with sketch and stand-up comedy, and usually a story arc where Leo learns a holiday lesson.
The show is back in Boston at the Chevalier on Dec. 6 with musician Nellie McKay and comedians Paul F. Tompkins and Stoneham native Josh Gondelman.
“Ted is very funny and a really good actor,” said Mann, speaking by Zoom with Leo, “and it is really fun for me to interact with him onstage. And every concept for the theme of the show we come up with is always really dumb. There’s a dumbness factor that, for me, is a real attractant.”
Christmas comedy can be wrought with cynicism for tidings of good will hollowed out by ads for cars and appliances. To Leo, that’s not what this show is about. “It’s not an anti-holiday show, it’s not an anti-Christmas show,” he said. “We might absolutely sneak in our sentiments about commercialization, hardening of religious traditions that we don’t necessarily agree with, but dare I say, the spirit of Christmas, the holidays in general, it is absolutely something that I think everyone involved is invested in.”
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