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Holiday playlist getting stale? Freshen it up with these songs.

Sufjan Stevens Christmas
Sufjan Stevens' collection of Christmas songs is a good place to start if your holiday soundtrack needs an overhaul.

Growing up in a very music-forward household gives you a whole new way to keep time. You could wake up from a multi-year coma and, at the very least, figure out what month it is based on what’s coming out of the speakers.

That chronological feat gets even easier around the holidays. Whether it’s Mariah proclaiming that you are all she wants for Christmas or George Michael lamenting his heart being regifted, there are certain songs we expect to hear when reaching this section of the calendar (or try to avoid hearing, depending on whether you’re Whamageddon’ing).

While I was raised in one of those music-friendly environments, I don’t recall a lot of “latest and greatest” in the holiday soundtrack — unless you count Manhattan Transfer. My mom was the house DJ, which meant a lot of Nat King Cole as well (no complaints there). I think having music piped in almost constantly was what started me building my own seasonal playlist. And having it be largely traditional was what nudged me toward a more modern leaning selection.

In the olden days, the limitations of a burned CD meant you had to narrow it down to 15-ish songs — the cream of the cream of the cream of the crop. Streaming has since loosened the reins and allowed for the annual refinement process to be mostly addition and very few removals. More Kris Kingle and less Grinchy, to the point where my playlist currently sits at a robust 5 hours and 20 minutes.

With long drives, flights and family get-togethers still ahead of us, it seemed like a good time to share a handful of songs that may have escaped your notice. Take a listen and, if you like what you hear, use them to give your playlist a refresh.


“Everything Is One Big Christmas Tree,” The Magnetic Fields

I don’t remember exactly when this 2010 track found its way into my collection, but it’s held the title of my undisputed favorite Christmas song ever since. It’s exactly weird enough to slide in right alongside more conventional tracks while perking up ears with Stephen Merritt’s low-register vocals, a cheerful ukulele, a verse sung entirely in German and lyrics like this:

Why sit in your dark and lonely room?
Must your every word be sincere?
Here's a vial of laughing gas perfume
See that people smile when you're near
If they don't like you, screw them
Don't leave your fortune to them


“Get Down for the Holidays,” Jenny O.

It seems 2010 was a killer year for holiday tunes. This one was part of Target’s The Christmas Gig collection (‘tis the season for commercialism) and is a wonderful example of keeping things simple: just an acoustic guitar and Jenny O.’s enchantingly adorable vocal affectation. Like the ideal holiday party guest, it also leaves before overstaying its welcome, running a mere 113 seconds.


“Christmas in L.A.,” The Killers (feat. Dawes.)

Los Angeles will always hold a very special place in my whatever organ holds things you despise. Gallbladder? I’ve been there twice and would very much like to never go back. That’s one of the reasons I get such joy out of this song, which explores how absolutely dreadful it is to be in the City of Angels during Christmas. The other reason is The Killers enlisting another of my favorite bands to sing lines like:

My parents sent a Christmas Card and tennis shoes
"We understand you’re staying, and we’re proud of you"
There’s a well-rehearsed disinterest in the atmosphere
I don’t know if that’s what this town gave me or if it led me here


“Strangest Christmas Yet,” Steve Martin & The Steep Canyon Rangers

Apparently, there’s a rule stating that any artist releasing a Christmas song must include sleigh bells on said song. It’s staggering. For this yuletide track, Steve Martin went back to his subversive roots in two ways:

  1. No sleigh bells. Lots of banjo.
  2. Releasing the song in September.

Martin’s goofy sense of humor and seriously great banjo-playing (along with the equally accomplished Steep Canyon Rangers) prevent this from falling into the novelty song trap of diminished returns with each listen. It also goes over pretty well with kids.


“Christmas Song,” Phoebe Bridgers (feat. Jackson Browne)

Whew, talk about mood swings. On the heels of Steve Martin’s light-hearted approach to holiday get-togethers, we have Bridgers and Browne singing of the devastating emotional hangover that follows gatherings with family and friends.

Originally performed by Omaha duo McCarthy Trenching, this cover finds a comfortable place in Bridgers’ oh-so-sunny catalog with a strangely satisfying climax as she and Browne sing, “The sadness comes crashing like a brick through the window / And it's Christmas so no one can fix it.”


“That Was the Worst Christmas Ever!” Sufjan Stevens

I know what you’re thinking. You’re thinking, “I really enjoy banjo AND emotional devastation. Is there a Christmas song for me?” You bet there is! While the finger-picking isn’t nearly as fancy as Martin’s, the banjo on this one is an interesting accompaniment as Stevens commits to tape a vivid tale of holiday disfunction:

Our father yells
Throwing the gifts in the wood stove, wood stove
My sister runs away
Taking her books to the schoolyard, schoolyard

If this isn't quite your cup of eggnog, worry not. Stevens has something for everyone in his Songs for Christmas collection.


“Like a Gift from God or Whatever,” Chris Farren (feat. Jenny Owen Youngs)

It feels like a good time to lighten things up, which means it’s a good time to call on Chris Farren. A frequent collaborator with the like-minded Jeff Rosenstock, Farren tends to find room to have fun with the listener, although this song off his 2014 Christmas album plays it pretty straight. While I’m not sure if the lovebirds he sings about are separated by distance or just plain separated, it’s still a bouncy little track with a singalong chorus.


“My Dear Acquaintance (A Happy New Year),” Regina Spektor

There’s a sneakily large music marketplace dedicated to the calendar’s turning over — Death Cab for Cutie’s “The New Year,” Dan Wilson’s “What a Year for a New Year” and Chris Thile’s “Modern Friendship,” for example. This cover of Peggy Lee’s 1983 song maintains the sweetness of the original while diluting it with sounds of conflict to remind you that the world isn’t a sweet place. I’m not sure about those touches, but Spektor’s inimitable voice and sincere “Happy New Year” wish at the end always get me.