Christmas music has a way of finding you whether you ask for it or not — in airports, hotel lobbies, grocery store aisles, and everywhere in between. Over the years, I’ve found myself gravitating toward the songs that slip in sideways, the ones that feel a little strange, a little unexpected, and sometimes even comforting in their oddness. These aren’t the tracks blasting from every speaker in December; they’re the ones I return to when I want the season to feel more human, more reflective, or just a bit off-kilter. Consider this a holiday playlist for anyone who likes their Christmas music with a twist.
Christmas Songs with a Twist
Fisher – “Christmas Face”
One of my most favorite people in music, I featured this song in Christmas 2020, this song has been a fave to fire up while I have been overseas and away from loved ones. Katy’s voice is beloved by so many.
The Cocteau Twins – “Frosty The Snowman”
If you have never heard Liz Fraser singing, she is one of the most incredible female vocalists of all time. If you HAVE heard her sing, you know this is one of 3 songs you can actually know what she is singing about. She uses her voice as an instrument, and makes a word salad, so you just listen to a stream of words that make no sense. There are “Rosetta Stone” classes to learn “What the **** Is Liz Fraser singing about”. This time around, you know what she is singing, and I have to say, probably the best version of the song I have ever heard.
U2 – “Driving to Midnight Mass on Dublin Christmas Eve”
This song is a bootleg recording of Bono just reading a poem to some very early U2 music demos they taped prior to even having an album. I scored this vinyl in high school, and it still has some of the most stripped down feelings.
Love them or hate them, this one from U2 is raw and magical.
David Bowie and Bing Crosby – “Little Drummer Boy”
This was a crossover piece of wonderful music history. As Bing Crosby was getting older, and being less relevant, suddenly David Bowie and Bing do this duet. Bowie sang several lines improvised, working off one of his heroes, a classic performer to David Bowie, now it’s a classic to all of us.
I know Bing Crosby’s grandson (Who is a Jazz Crooner himself), and he had some great stories about that family.
Monty Python – “Christmas in Heaven” from “The Meaning of Life”
I had to pull this one up, for the laughs, and had to save it for last. Monty Python were all about offending the sensibilities of religious people, hell “The Life of Brian” was banned by so many church groups, it got them massive publicity for it, and made the film a critical success.
“The Meaning of Live” was no different, only this story is a bit darker. Graham Chapman the actor who played Tony Bennett in this video was gay. He kept it as an open secret in the industry for so long. He was a train wreck with drinking and trying to hide who he really was for the better part of the 70s. He passed away in October 1989. Enjoy this clip, especially the advice at the end.
Taken together, these songs remind me that Christmas doesn’t have to sound just one way to feel meaningful. Whether it’s reverent, strange, funny, or quietly emotional, there’s room in the season for music that reflects where we actually are — not just where we’re told we should be. These tracks have followed me through different years, different cities, and different versions of myself, and they continue to offer something familiar without being predictable. If nothing else, they’re proof that even at the most traditional time of year, there’s beauty in choosing something a little unexpected.
