“O Holy Night” by Ben Caplan
The thundering folk star himself goes for Baroque with this holiday standard, making it the prime opening slot on this playlist: Its slow-building anticipation is perfect for waiting for the first guests to (virtually) arrive.
“The Banister Bough” by Chilly Gonzales feat. Feist
Collaborations between Canada’s premiere songbird and musician-producer Gonzales are always solid gold (see the Gonzales-produced Feist album Let It Die for proof). This, the duo’s first-ever holiday hit, proves no exception as it tickles your every vertebra with warm piano and soaring vocals.
“Make You Mine This Season” by Tegan and Sara
When it’s time to kick the party into high gear, this glossy synth-pop gem is what you need—especially since it sounds so in the wheelhouse of the Quinn twins you’d barely know it was a holiday track if you weren’t paying attention to them sing “you’re the only girl I’ve got on my list.”
“Kisses for Christmas” by Christina Martin
Warm, jaunty and mid-tempo: Martin’s new holiday single is not only a catchy-as-hell reminder of what matters most this time of year—it’s also the perfect mood music.
“Downtown Christmas Eve” by Jenn Grant
If you ever doubted that a holiday song could double as a baby-making anthem, well, you’ve never heard Grant’s ode to life in a winter wonderland.
“Jingle Bell Rock” by Serena Ryder
Not since Regina George has someone made this rock ’n’ roll song slap so hard.
“It’s Beginning To Look A Lot Like Christmas” by Anne Murray
The grand dame of Nova Scotia’s folk tradition is back with the sort of album made for tinsel-edged days. Get into it as she tackles silver-throated standards like this one.
“Merry Xmas Everybody” by Sloan
This John Lennon-feeling 2012 holiday hit still holds up.
“Little Road to Bethlehem” by Don Brownrigg feat. Rose Cousins
A slow, sweet folk lullaby that’s perfect for deep conversation.
“Then It Snowed” by Gabrielle Papillon
A soaring, pop-tinged song that will make the moment feel like it stepped straight out of your favourite holiday movie.
“Do You Hear What I Hear?” by Destiny’s Child
Transport yourself to the days of girl power and butterfly clips with this early 2000s holiday staple.
“All I Want for Christmas Is You” by Mariah Carey
The GOAT of holiday hits helps end your Zoom call on the perfect, vibrato-soaked note.