A Christmas Playlist You’ll Actually Want to Listen To

It follows you everywhere, from your car to the mall to the grocery store and back home again: Christmas music. And not a huge, wonderful, diverse collection of Christmas songs, but a crappy selection of the most grating tunes — we’re thinking about clunkers like “Little Drummer Boy” and “Holly Jolly Christmas.” It’s enough to make a person cover their ears and scream… or at least turn off the radio and sit in utter silence.

But here’s the thing: There’s actually a lot of great Christmas music out there. It just doesn’t get played as much. In a lot of cases, you have to go seek it out. And that’s what we’ve done for you below. Here’s our best mix of surprising people playing classics, indie rockers penning their own original holiday tunes and even a couple of amazing, timeless classics to balance everything out and make your mother happy.

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Catie Curtis — “Lo, How a Rose E’er Blooming”

We love mixing up a super-old classic hymn with a modern singer to create a quality Christmas song. In this case, folk-rock star Catie Curtis covered “Lo, How a Rose E’er Blooming,” layering her voice in harmony over simple string instrumentation. It is just very, very haunting and simple and melancholy and pretty.

John Prine — “Christmas in Prison”

Well, this is one of two songs on our playlist that involve spending the Christmas holiday behind bars — I guess we’re just rebels like that. This one comes from legendary country singer John Prine. We love the beautiful poetry of the lyrics that contrast the bleakness of prison with the magic of the season, like this heartbreaking verse: “The search light in the big yard turns ’round with the gun/And spotlights the snowflakes like the dust in the sun/It’s Christmas in prison there’ll be music tonight/I’ll probably get homesick, I love you, Good night.”

Low — “Just Like Christmas”

Duluth indie rock band Low has one of the best modern Christmas albums out that we know of, 1999’s Christmas. The album mixes original holiday tunes with classic standards like “Little Drummer Boy,” “Silent Night” and “Blue Christmas,” all with their low-fi sound and boy-girl vocals. It’s all worth a listen, but our favorite track is “Just Like Christmas,” with its contrast of cheery sleigh bells and bittersweet lyrics.

James Brown — “Santa Claus Go Straight to the Ghetto”

Yes, we definitely want a track on our playlist from the Godfather of Soul. This is the opening track from Brown’s 1968 Christmas release, A Soulful Christmas, and it is like the exact opposite of so many of the straight-laced, boring holiday tracks we hate. In it, Brown pleads with Santa to skip everyone else and get some presents to the kids in the ghetto — and ends with the super-pleasing line, “Tell him James Brown sent you!”

The Waitresses — “Christmas Rapping”

This is weird and we love it. Released in 1981 as part of a ZE Records Christmas compilation, this sort of almost rap song by The Waitresses is a wonderfully joyful and quirky tune that absolutely has to go on any nontraditional Christmas playlist. Our favorite part, aside from the killer bass line, are the lyrics, which detail a single woman who isn’t feeling the Christmas spirit at all until she runs into her crush at the store. It’s as endearing as things get, like this line: “I’m hardly dashing through the snow/’Cause I bundled up too tight.”

Björk — “Frosti”

Every Christmas playlist needs an instrumental, and this one comes from oddball Icelandic singer Björk. Off of her album, Vespertine, this two-minute interlude has a wonderful, magical music box vibe that somehow really captures the feel of winter. We’re honestly not sure if this is strictly a Christmas tune, but it’s called “Frosti” and it sounds pretty festive if you ask us.

Joni Mitchell — “River”

Off one of the best albums ever recorded, Blue, this Joni Mitchell song has us weeping into our eggnog every time it comes on. This is probably the emotional opposite of tunes like Here Comes Santa Claus — it’s about breaking up with your lover over the holidays and just wanting to escape it all. Still, it’s sad in that good-sad way, and it creates a good balance so you don’t get too overly joyful while listening to holiday music. No one wants that.

Pogues — “Fairytale of New York”

This is an epic Christmas song, and it’s widely considered the best Christmas song ever recorded by those in the U.K. and Ireland — as well as anyone with good holiday music taste in our opinion. Written by Celtic punk band The Pogues, it’s a modern take on a traditional Irish ballad that follows an ill-fated couple through their Christmas holiday, and things don’t go well. It begins in a drunk tank and ends with the town’s bells ringing on Christmas morning — and we enjoy playing it on repeat.

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Aimee Mann — “Calling on Mary”

Aimee Mann has a pretty OK Christmas album called One More Drifter in the Snow that mostly contains classics. While we’re pretty meh on the effort in general, we do love the album’s two original songs, “Christmastime” and “Calling on Mary.” “Mary” wins out in this playlist because we love the jazzy piano and Mann’s smooth voice. It feels like a holiday classic you just haven’t heard yet.

Kanye West — “Christmas in Harlem”

It is pretty hard to find a good rap or hip-hop song about the holidays. Too many of them come out sounding corny or forced or don’t capture anything special or real about the season. Enter Kanye West’s effort, “Christmas in Harlem,” to show everyone how it’s done. This track features rapper Cyhi the Prynce and West’s protégé Teyana Taylor, and it’s witty, joyful and warm, especially with Taylor adding cheer.

Tom Waits — “Christmas Card from a Hooker in Minneapolis”

File this under melancholy holiday songs: It’s a piano ballad off of Tom Wait’s 1978 album, Blue Valentine. The entire song is a first-person letter from a sex worker to a man named Charlie. In the letter, the sex worker opens her heart about her life and circumstances. Even though this seems like a downer, there is something warm and joyful in the song, and we think it does a great job of mixing up any holiday music playlist that is leaning too much toward the corny.

Sufjan Stevens — “Ring Them Bells”

Wow, indie rock singer-songwriter Sufjan Stevens really, really likes Christmas. To prove it, he’s recorded about a million Christmas songs, including two five-disc box sets of songs, one called Songs for Christmas in 2006 and one called Silver & Gold in 2012. We think that is absolutely and entirely way too many Christmas songs, but we do like a few of his efforts. “Ring Them Bells” is a Bob Dylan cover that appears on the movie soundtrack from I’m Not There.

Bob Dylan — “Must Be Santa”

Speaking of Bob Dylan, he released a very weird Christmas album in 2009. In it, he covers many of the classics in his own Dylan way, proving that Christmas can be odd and that Bob Dylan can do basically whatever he wants and it’s OK. Our favorite track off the album, which has become one of our favorites, is “Must Be Santa.” It is full of roaring energy and weirdness, and we wouldn’t have it any other way.

Judy Garland — “Have Yourself a Merry Little Christmas”

OK, we need a couple of classics on our playlist to even everything out. Our first pick is Judy Garland’s timeless version of “Have Yourself a Merry Little Christmas.” Her voice is absolutely stunning in this song, and it doesn’t have any of the corniness that can sneak into other renditions. We love it when she sings, “Until then, we’ll all muddle through somehow.”

Tori Amos — “Star of Wonder”

In 2009, Tori Amos threw her Christmas music hat into the ring with her girl-and-a-piano effort Midwinter Graces. The daughter of a Southern preacher and someone who has a complicated view of religion, it’s no surprise much of the album is haunting and weird. However, we love how she blends classic hymns with her own music and lyrics. Our best pick for the playlist: “Star of Wonder.”

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Elvis — “Blue Christmas”

Let’s end with one more classic. No matter how many people try to cover “Blue Christmas,” there is only one person who can do it with the emotion and smoothness of Elvis… and it is Elvis. Sure, we hear this on the radio and at the mall during the holidays, but we never get sick of it. It’s one classic that can stay.


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