Misfit Toys

Offbeat and Obscure Holiday Music.

Not to brag, but Santa got me my JAM5 last December. My friends at the Trulli workshop kindly put me on their tester’s list in 2020. So inevitably, that first month it mainly rocked holiday music.

This was oddly perfect. The added frequencies instantly stood out since I knew these songs well, but only hear them once a year. “Baby, Please Come Home” by Darlene Love sounded magical with more definition and bass. Of course, the song hit harder because like millions of others last year the pandemic kept me from traveling home to be with my folks.

All I could do was listen to “Blue Christmas” on the JAM5 and picture Mom and Dad dancing to the King like they do every year. My dad has always loved holiday music. I grew up on Vince Guaraldi and Nat King Cole, naturally, but also funkier stuff like James Brown and Booker T. & the MGs Christmas records. We like the deep holiday cuts in my family. I suspect we’re the only ones still playing our The California Raisins Present A Claymation Christmas Celebration cassette.

Today, it’s not officially the holidays in my house until Shane McGowan and Kristy MacColl snarl unforgivable things at each other. I love offbeat holiday music. The sour glory of “Fairytale of New York” and the Ramones’ “Merry Xmas (I Don’t Want to Fight).” The wild self-promoting hype of James Brown’s “Soulful Christmas Tree” and “Let Make Christmas Mean Something This Year.” John Denver’s funny-sad-funny “Please, Daddy (Don’t Get Drunk This Christmas)”—criminally got left off his Muppet holiday album.

I don’t think of myself as an indie Scrooge. ’Tis the season to either enjoy Bing and Mariah or go insane fighting them. I say, bring on the classic carols. Just know there’s other fantastic stuff hiding out there; forgotten novelties tracks, bargain bin gems and unheard shoulda-been hits. I’ve been collecting them since the blog ages. Perhaps I hope I will them to the top of the charts one day. Or at least they become seared into my own kids’ memories.

In the spirit of giving, here are some of my favorite misfit toy holiday songs. I did not include covers because there are too many great versions to count. I can no longer say whether I ironically love or love love. I just know I love them.

“I Want An Alien For Christmas”

Fountains of Wayne

An infectious power-pop earworm about begging Santa for a pet ET. It’s both a parody of silly ’50s/’60s novelty holiday songs and authentically captures what it feels like to be seven and wishing with all your heart for a ludicrous present. RIP Adam Schlesinger, who passed from Covid last year. He carried on the proud tradition of Jewish songwriters making the best Christmas tunes (“White Christmas,” “Let It Snow,” “The Christmas Song,” and more).

“Truckin’ Trees for Christmas”

Red Simpson

’70s CB country at its festive finest! This song was on an entire album of trucker-themed Christmas music by Simpson. One listen, and the movie adaptation writes itself. Gimme a 10-4, and let’s do it, Hallmark Channel.    

“Backdoor Santa”

Clarence Carter

Soulman Carter delivers perhaps the funkiest and naughtiest Santa song of all time. Seriously, not kids stuff. This Santa carries on illicit affairs with housewives while leaving the backdoor open for hasty escapes. Adult listeners will note the horns were sampled for RUN DMC’s “Christmas in Hollis.” 

“I Ain’t Gonna Let You See My Santa Claus” 

Victoria Spivey  

Actually, this is probably the naughtiest Santa song of all time—and from 1936, no less. Blues pioneer Spivey recorded with King Oliver, Louis Armstrong and even a pre-fame Bob Dylan. With non-stop innuendo, I can’t believe this hasn’t had an empowered modern cover by now.    

“Christmas Blues”

Saturday Looks Good to Me

Motown-inspired lo-fi pop from Ann Arbor, Michigan. SLGTM-mastermind Fred Thomas built a vast catalog of other projects and under his own name over the last 20 years (he also just released a podcast on the history of Polyvinyl that I can’t wait to dive into over the holidays). I adore the wistful, guileless vocals. Midwest flurries always feel like they're about to start when I hear it.    

“Boxing Day Blues (Revisited)”

Courtney Barnett 

Recorded as a single at Third Man in Nashville, this is another sad one. For those who didn’t grow up in a commonwealth country, Australian Barnett is singing about the day after Christmas on the 26th, which is either a day to honor your servants/give to the less fortunate/snap up post-holiday deals/or in this case take down your decorations. A great beat and a great jilted lover’s lament. 

“Hey Santa Claus”

The Moonglows

A group that proves you can be in the Rock ’n’ Roll Hall of Fame and still be under-appreciated. This bobbing R&B song was the b-side of the (at least to me) not-nearly-as-great “Lonely Christmas.” This song also way predates a young Marvin Gaye joining the group near the end of their Chess Records run.

“Yuletide Throwdown – Remix”

Blondie & Fab 5 Freddy with Cut Chemist

New for this year, Cut Chemist has brought fresh cheer to this old downtown collab. OK, Debbie Harry was not much of an MC, but this remix saves the day by upping the ante on the old-school cheer. 10 outta 10 lords-a-leaping agree.   

“Christmas at the Zoo”

The Flaming Lips

A festive fable, but I have no idea what the moral is supposed to be. Freed zoo animals refuse to leave their cages on Christmas eve… and wild mutant Clouds Taste Metallic-era guitar noises. I like to think of it as the theme from an abandoned holiday cartoon that Dr. Seuss and Chuck Jones never completed.

“Christmas In Jail”

The Youngsters

Here the moral is pretty obvious: Don’t drink and drive, people. There are a surprising amount of songs in this micro-genre: The aforementioned “Fairytale of New York,” John Prine’s “Christmas in Prison” and Johnathan Coulton & John Roderick’s “Christmas in Jail,” and Leroy Carr’s “Christmas in Jail, Ain’t that a Pain.”  

“8 Days”

Sharon Jones & the Dap-Kings

With apologies to Adam Sandler, Hanukkah deserves way more great jams. (2019’s Hanukkah+ compilation is worth a spin.) The late, great mighty Sharon Jones delivered a classic with the swinging soul perfection of this undeniable classic.  

“We Wanna See Santa Do the Mambo” 

Big John Greer

Digging through discarded holiday music is like musical archeology. You can sift through every fad of the last 100 years and find a corresponding Christmas track. (For proof, check out the Turtle’s “Santa and The Sidewalk Surfer” or King Diamond’s black metal “No Presents for Christmas”). Maybe Greer and his band were just cashing in, but there is absolute joy in their performances. “Mambo Santa Mambo” by the Enchanters is also pretty dope.

“Everything’s Gonna Be Cool This Christmas”

The Eels

E. of the Eels has written his share of heartbreakers. And while this time of year can be brutal, this rocker is a fun testament to surviving the holidays and staying hopeful. Listen if only to hear E. say, “Baby Jesus, born to rock” at the drum break.

“Crazy Santa Claus”

The Debonaires

Impossible to choose if this is better than “Dig That Crazy Santa Claus” by Oscar McLollie. It’s a holiday hepcat showdown, and at least one sax player is going to get taken out by a zip gun.  

“Lady December”

The Concretes 

Not explicitly a holiday song, but it’s nice to sprinkle in some general snow/winter tracks on your holiday playlists. This is gorgeous Swedish indie pop for whatever solstice celebration you honor. The refrain “forgive and forget” also seems in the spirit of the season.  

“Trim Your Tree”

Jimmy Butler

OK, boomer. I really can’t stop with the forgotten soul. There’s just so much of it. I swear I am leaving so many others off this list. Nancy Meyers, let me pick the music for “The Holiday 2: Electric Igloo.”   

“Christmas Unicorn”

Sufjan Stevens 

Sufjan has put out two giant holiday collections, an endless advent calendar of unexpected treats. The weirdest of all is this 12 and half minute track that tries to decide what the heck Christmas even stands for nowadays. Not an office party banger by any means, but worth a full listen at least once a year to remind me to embrace this beautiful and strange time of year in all of its endless forms. Alright, that is as sappy as I’m getting. Yell at me on Twitter with all your weirdo favorites I didn’t list. Merry Xmas, you filthy animals.


Scott Serilla

Freelance Contributor

Scott is a writer who loves tacos, rock ’n’ roll and comedy. He lives on the north side of Chicago with his wife, kids and dog. Follow him @metropotamia