12 Obscure and Under-appreciated Holiday Tunes to Grow Your Street Cred Three Sizes Today!

Christmas Remixed was a series of CDs that came out in the early 2000s, and one of my absolute favorite albums. Some of the attempts to remix these songs are more successful than others, but I love Happy Holiday Beef Wellington mix. It’s got Bing Crosby’s vocals, which who could ask for more. But beyond that it also brings a proto-swing-hop charm. This one snuck by on the JCPenney playlist when I used to work there in the 2010s, but I think other than that it’s not widely known, but that’s probably why I associate  it so much with a busy mall. Either that or the ad-like bridge section. Either way, this naughties recapitulation of an Irving Berlin classic is a joy.

~ Geo

I love this song. A lot of people don’t know that it was originally written for the musical Mame, starring Angela Lansbury (one of the reasons one of the most popular renditions of this song is hers). The musical is about a wealthy socialite welcoming an impoverished nephew into her life when he becomes orphaned. 
With that snippet of context, I feel like the song comes to life. It’s about remembering to allow ourselves to enjoy the bits of celebration that we might otherwise feel ourselves too busy for. It’s about the little bit of surrogate joy that comes from creating a magical Christmas for someone else. That hits home for me as a parent. I’m ultimately choosing the Andy Williams version for this list for no better reason than because it caters best to my personal taste for 90s easy listening schmaltz.

~ Geo

This track is one that actually seems to get a lot of play in British Christmas movies and specials, and it’s easy to see why for me. Merry Xmas Everybody fills a niche in Christmas music that can be hard to fill. It’s simultaneously secular, upbeat, nostalgic, all while still managing to still sound like a Christmas song. This is one that gets brought out for every Christmas get-together and road trip for me. Essential to the vibe that I want to be putting out over the holiday season.

~ Geo

Just a really good song. Half the challenge of putting a Christmas playlist together is making sure it isn’t too samey, so why not put a Japanese punk song on there?

~ Geo

All I have to say about She and Him is that they have at least two full length holiday albums out and it’s Zooey Deschenel singing Christmas songs. We all know she stole the show in Elf, so if you don’t have She and Him on your Christmas playlist then you’re missing out.

~ Geo

Before there was Sabrina Carpenter, there were other Carpenters. The Carpenters, in fact. This gets a lot of airplay near me, and I don’t think I’ve ever heard another person aside from me and my spouse admit to liking it. I think people can find its earnestness off-putting, but I love this song. It’s nostalgic, hopeful, honest, and I love that. It’s Jazzy and smooth, like spending a winter evening sipping mulled wine with your main squeeze. Highly recommended.

~ Geo

Christmas Wrapping by the Waitresses is another one of those ones that most people have probably heard before, but which deserves a closer look. It’s often used in movies as a backdrop, but I had never heard it on its own until I sought it out. This song to me embodies the frenetic energy of preparing for company on Christmas Eve. It follows the We Didn’t Start the Fire school of lyricism: list a bunch of things in a stream of consciousness and hope something evocative falls out, and here’s the thing: it absolutely works. No notes.

~ Geo

Daďi Freyr is an independent electronic artist from Iceland. He rose to prominence through Eurovision and was featured in Just Dance 2023. I’ve been following his work for a year or so and have been consistently impressed with his stripped down aesthetic and ability to recontextualize songs he covers in surprising ways, while keeping their essential elements in place. I was pleasantly surprised when he dropped a Christmas album last month. Of course the covers on the album qualify for the same high praise I already gave, but I wanted to feature one of Daďi’s original tracks on the album. Something Magical celebrates the timeless elements of Christmas, and is a certified bop. I dare you not to tap your foot to this song.

~ Geo

Sneaking in a sad one here. I like the word play between home alone, too and home alone 2. Is that reason enough to include in this list?
Yes, but I’ll also say that the commentary on how media fits into our traditions and how going back to traditions when we leave people behind, whether from a breakup or other situation, can make engaging with that great media more complicated.

~ Geo

Sometimes it seems like the only enduring legacy of the unfairly maligned The Grinch (2001) starring Jim Carrey is the Faith Hill song Where Are You Christmas. The soundtrack for that film is stacked with early naughties superstars like Smashmouth, Trans Siberian Orchestra, Ben Folds and Eels. My pick from the litter though is Green Christmas by Barenaked Ladies.

Right from the beginning, the plodding chords and bouncy melody give this a very distinct holiday feel. This song is perfect for the movie because both textually and musically, it brings to mind a feeling of being left out on Christmas, or perhaps just the dissonance of being in a bit of a bad mood with all this jolly decor around. Having this song on your playlist offers a bit of emotional nuance without clashing with the overall aesthetic of the season.

~ Geo

The name Herb Alpert might not ring a bell for most people (pardon the pun). But I think most would recognize at least a piece or two of his work. Alpert was most famous for his brass-centric easy listening music. In 1968, he released Christmas Album, featuring classics in mostly his signature style. However also on that album is a rich vocal arrangement of an obscure song Burt Bacharach wrote for Bobby Vinton.
The smooth arrangement is a great change of pace for a very bright and brassy album, but even outside of that context, it’s a nice smooth Christmas tune that’s off the beaten path.

~ Geo

If one body of work deserves more time in the holiday spotlight, it’s Sufjan Steven’s sprawling 4-CD Masterpiece, Songs for Christmas. With a loving, handcrafted feel and eclectic instrumentation, the album is equal parts prayer, Christmas party, and singalong. Shining especially bright are Stevens’ original songs on the album. Each one feels genuine and right at home nestled among the dozens of classics that comprise the album. 

Choosing just one track from this album was a difficult task. It came down to which song I most wanted people to know existed, and for me it’s Get Behind Me Santa: a cheeky meditation on holiday overstimulation and the impossibility of belief a la Sympathy for the Devil which contains the line “I’m just another regular guy / with superpowers and a penchant for the Yuletide”. 

~ Geo

Celebrate Me Home is a sentimental classic that captures the longing of wishing that you were at home celebrating with the people who you love. In this song, Loggins somehow eschews many of the tropes of writing a Christmas song while still capturing a universal feeling of the holiday. Here you’ll find no driving beat, no sleigh bells, yet this definitely has the soul of a Christmas song. Celebrate Me Home is Home for the Holidays stripped down to raw, human longing. It pleads with us to empathize, “It’s cold out there, and I am not where I wish I was.” With all its emotional weight, Celebrate Me Home is hopeful. It builds to the end with a triumphant bridge.

Celebrate, Celebrate, Celebrate me home

The choir intones, almost as if trying to do Loggins’ bidding and be the celebration that will carry him home. Kenny joins the choir with a reprise of the chorus, and the fade out begins, calling you to imagine him being carried off, whether in reality or imagination, toward the loving reception back home he wishes he could have.

~ Geo