A Very Bleeding Heart Christmas Playlist

For some (like me) Christmas festivities already get rolling tonight. With the help of the right music, they can get rocking, too. Just in time for your Christmas gatherings, may I present to you The 12 Songs of Christmas - A Very Bleeding Heart Christmas Playlist

In no particular order, here are 12 songs that swing from deep meaning to deep fun. Some old favourites mixed in with some you might have missed. Even some from friends of Bleeding Heart Art Space. All of these gems would be welcome at a Bleeding Heart Christmas party, with the hopes that someone would track down the host to ask, ‘who is this singing?’ at least once. 

ONE: Christmas Must Be Tonight


I discovered this gem last year, and Bahamas does an incredible job covering The Band’s tune that brings us right back to that baby in the stable. A little bit of confusion and wrestling with this cosmic event thrown into the lyrics add some weight to this classic.

TWO: Peace On Earth/Little Drummer Boy

Bing Crosby and David Bowie

I know. Bing Crosby and David Bowie! This song is weird, and the cheese gets real gooey at some points. It feels like the audio version of a 'very special Christmas special’. But still, there is something here, inside all that cheese, that rings true. When David Bowie sings ‘Peace on earth, can it be?’, I’m sold.

THREE: The Coldest Night of the Year

Bruce Cockburn

Not exactly a Christmas song. Maybe more of a solstice song? Something about the heartache and loneliness in Bruce’s voice gets near the depths of the pain a Christmas can bring when those we love are far away, for now or forever.

FOUR: Have Yourself a Merry Little Christmas

John Denver and The Muppets

A Christmas Together should be owned in its entirety. John Denver and the Muppets made an entire album of Christmas classics. This track features the gruff voice of Rowlf the dog in a leading role, and somehow it suits the nostalgia of this tune perfectly.

FIVE: Carry My Home

Hey Rosetta!

Another Christmas album you need is Hey Rosetta!’s A Cup of Kindness Yet EP. Just five tracks but every one shines. None so bright as this original tune where the band captures universal feelings of homecoming at Christmastime. And boy does it groove. If you are driving home for Christmas, crank this tune.  

SIX: O Come O Come Emmanuel

Karla Adolphe

It’s hard to inject any new life into a song with such a haunting and strong melody. Our good friend Karla Adolphe did just that last year on her Christmas EP, Lingering. This gorgeous production captures the anticipation and longing of this classic hymn. 

SEVEN: Last Christmas


Total eighties glory on display here my friends. Put this on and just try to keep your toes from tapping. How can a song be so happy and so sad at once?

EIGHT: Wonderful Christmastime

Paul McCartney

Let’s give that eighties cheese wheel a spin and land right about here. Dead centre in the weird electronic wandering of Paul McCartney. Right here, right in the melancholoy of this tune that is supposed to be all joy, things click. Am I the only one who doesn’t believe this Christmastime is totally wonderful? Maybe it’s the weird instrumentation choices, but I hear some cynical disconnect here, and I like it.

NINE: Zat You, Santa Claus?

Louis Armstrong

This song is weird. And creepy. And perfect for the weird creepiness that is Santa Claus. Sure we love him, but sometimes he does seem just a little odd, keeping his tabs on our behavior from who knows what surveilance, creeping around in the dark and sneaking into our living rooms. This song is just as fun as any Louis Armstrong tune (Baby, It’s Cold Outside, anyone?), but also a bit on edge. 

TEN: Maybe This Christmas

Ron Sexsmith

“Maybe this Christmas will mean something more …” One of Canada’s more stalwort songwriters brings us a true Christmas classic that I return to every year, stomping my heels lightly along with this plea for peace and forgiveness.

ELEVEN: Only at Christmastime

Sufjan Stevens

From the creative powerhouse who has brought us dozens of Christmas songs by now – some hits and some misses to be sure – comes this gorgeous original. Like the best Christmas songs, it holds up outside of the season, after ’the magic’ fades. If you, like I had, forgot about this one, have another listen.


TWELVE: Bethlehem

Over the Rhine

This song is just beautiful enough to hurt your heart. Not break it, but perhaps leave a crack or two? The lyrics take us right back to the ‘true meaning of Christmas’. We’re reminded that 'Jesus was a refugee'. We’re reminded that ‘Mary, she was just a kid’. 

‘Sometime’s there’s no difference’, we are told, ‘between a birthmark and a scar’.

Find this one on the absolutely fabulous OTR Christmas album Blood Oranges in the Snow.

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