Holiday Music that Made Jasmine & Hailey

From classics we grew up with to new originals and those perfect not-really-about-Christmas winter songs, this is the holiday music that made Keepsake House co-founders Jasmine & Hailey.

In this blog series, we post playlists co-curated by Keepsake House artists that include their greatest influences, childhood favorites, and even guilty pleasures… the Music that Made them.

It’s the first of December, and all through Keepsake house, everyone is singing, even a mouse? Forgive us, but we’re fans of the holidays, particularly the music they bring. Our very first blog post featured the music that made us, so it feels only fitting to provide an updated, holiday version. Read on to hear about the holiday songs that Keepsake co-founders Jasmine and I (Hailey) grew up with as well as the ones we grew up to, and listen along via the playlist embedded below, The Holiday Music that Made Jasmine & Hailey.

Because there are too many incredible holiday songs, we’ve broken this up into a few sections…

The Classics

We begin with Frank Sinatra’s “Jingle Bells,” a choice that may seem odd for us but is bound to one of Jasmine’s most treasured memories. Growing up, she and her sister had a Christmas Fake Book that they would dig out every holiday season and play (literally) a song from every night for the entire month of December. It probably drove their parents up the wall. When they were kids, they arranged this crazy version of “Jingle Bells” where their hands crossed over each other’s and it would get faster with every repeat of the song. Jasmine thinks they played it at a piano recital one year. [Editor’s note - we need a recording!]

The only suitable follow-up to Frank Sinatra would be the incredibly silly “I Want a Hippopotamus for Christmas” by Gayla Peevey, my absolute favorite Christmas song ever. I blame this song for the many hippo stuffed animals my parents received as presents over the years, and my unabashed love of every corny Christmas trope.

A few under-appreciated classics are next, including “Caroling, Caroling” by Natalie Cole, the daughter of Christmas king Nat King Cole. This is the version I grew up with, along with every other Christmas album Natalie Cole released. To me, she was always the Christmas queen. Harry Connick Jr. was another holiday icon in my house, and I most enjoy the track “Sleigh Ride.” While I always associate the holidays with snowy Vermont and Canada, I also spent a few years of my childhood in southern California, years that I call back to here with The Beach Boys’ “Little Saint Nick.”

“Merry Christmas, Darling” by the Carpenters is essential holiday listening. Jasmine’s parents didn’t really listen to holiday music, but if this ever popped on the radio, they would both be singing along quietly. Every time the song plays, she can imagine their voices singing alongside Karen Carpenter.

Next is a sub-section of two UK classics that I’ve always been obsessed with: “Happy Xmas” by John Lennon and Yoko Ono, of course, and “Merry Christmas Everyone” by Shakin’ Stevens. The latter might just be the most joyful song ever recorded.

The best classics are arguably saved for last here, with “Christmas Time is Here” from A Charlie Brown Christmas, “Feliz Navidad” by José Feliciano, and “Have Yourself A Merry Little Christmas” performed by Judy Garland from the movie musical, “Meet Me In St. Louis.” If the film isn’t on your annual holiday watchlist, add it now (along with “Die Hard,” which is also a Christmas movie, and you can’t argue with me about it).

And if Joni Mitchell was on Spotify (not that we blame her—go Joni), her original version of “River” would be here too, which brings us to…

The “Better” Versions of Classics

“River” is our mutual favorite holiday classic, but neither of us heard Joni’s version first. It wouldn’t be fair (or possible) to call any version “better” than hers, but we’re thankful for the versions that helped us discover the song: from Sara Bareilles and Robert Downey Jr., the latter a surprisingly great take from Ally McBeal that is included here. We’ll get to Sara soon.

A string of duets comes next: “The Christmas Waltz” by Johnnyswim (I stand by this being the best version ever recorded of this song), “Baby, It’s Cold Outside” by John Legend & Kelly Clarkson (you really can’t listen to any other version of this sexist song except this one, whose lyrics have been updated for the times), “Christmas for You and Me” by Drew Holcomb & The Neighbors (I saw them perform this live at their holiday show in Nashville when I spent a Christmas there with my parents, one of my fondest holiday memories), and another version of “Have Yourself a Merry Little Christmas,” this one a vocal masterclass by Darren Criss (whom I have loved since his Starkid days, and how could you not love Criss-mas?!) and Lizzy McAlpine.

Leslie Odom Jr. of “Hamilton” fame has become another classic Christmas crooner. Jasmine always loved to sing ”The Christmas Song,” a song that followed her as she started to come into her own voice as a performer. She chose to include Leslie’s version because his voice is “objectively angelic.” Angelic covers continue with Laufey’s “Christmas Dreaming,” which is aptly dreamy and filled with one of our favorite things (the cello), and “I’ll Be Home for Christmas” by Michael Bublé. Would a holiday playlist—or millennial childhood—be complete without this track?

I break up the slow songs with “Santa Baby,” one of my favorite Christmas songs that I feel conflicted by. I think I’ve grown out of hearing this sung by a sultry female voice, but I love when men sing it, and Nathaniel Rateliff’s version is pure country camp.

We end this section with the colored Christmases, both Blue and White, the former performed by Norah Jones on piano and the latter by Willie Nelson on guitar.

The Wrapping Songs

This is a short, sweet section all about wrapping and gifts. I’ve sequenced a cover of “Pretty Paper,” originally written by Willie Nelson, after a Willie Nelson cover. But this is Chris Isaak’s version, a gorgeous finger-picking, Hawaii-infused cover from a quintessential album that has been the soundtrack of my Christmas wrapping sessions for as long as I can remember.

Another album we both love is Kacey Musgraves’s “A Very Kacey Christmas,” and I’m particularly fond of “Present Without A Bow,” featuring Leon Bridges. The last two in this section are “Christmas Wrapping” by The Waitresses and “My Favorite Things” from another movie musical that was so formative for me, “The Sound of Music.”

The not-really-Christmas Winter Songs

“My Favorite Things” was not written as a Christmas song, which is why it is the perfect transition to our winter songs section, a.k.a. all those songs that are not really about Christmas, but we’ve all agreed to treat them as such anyway.

The first song here is “Winter Song” by Sara Bareilles and Ingrid Michaelson. If you’d like to see the two of us cover this song, be sure to attend or tune in to our upcoming holiday show, House for the Holidays. It’s free, and Jasmine is forcing me to sing this with her… ah!

“Winter Song” was made for the titular album by The Hotel Café in 2008, perhaps Jasmine’s favorite holiday compilation ever, so we included another song from this record: Brandi Carlile’s “The Heartache Can Wait.” These artists shaped both of us, but especially Jasmine, in her teenage years and songwriting journey. She used to sing this song with her sister Jess too, with Jess on violin.

“The Heartache Can Wait” is an original song about heartbreak that happens to take place at Christmastime, much like Taylor Swift’s “‘tis the damn season.” We are both beginning to embrace our inner Swifties, and I have to admit that I’m all in on the “evermore” era. The guitar (though electric) in this song is hypnotically repetitive, something I also love about the late Gordon Lightfoot’s “Song for a Winter’s Night.” I can’t speak or write about Gordon Lightfoot without crying, but he needs to be here.

In one of my favorite sequencing discoveries, we flow straight from “winter’s night” to “winter’s light” in another not-really-Christmas-song by Sara Bareilles, “December.” This may even be Jasmine’s favorite Sara song in general. The best way to listen to this song is lying on your floor with headphones on and hearing lines like, “But to get yourself a new life you've got to give the other one away / And I'm starting to believe in the power of a name / 'Cause it can't be a mistake if I just call it change.”

Keepsake Family

Speaking of names, the next version of “River” was released by Jasmine under her old performer name, Jay Miners. That’s right, we love this song so much that it’s included twice, and Jasmine loves this song so much that she performed and released a cover of it with her dear friend and guitar player, Sebastian Danalis. You can purchase it on Bandcamp here. This begins a slew of songs from our very own Keepsake family, with the short and sweet “hot chocolate” from corner club from one of the first records we reviewed for the blog, the adorably cozy “When It Snows” by Sarah Kang and Sam Ock, a cover of “This Christmas” by Moyana Olivia and Josh Fleckner that will knock your stockings off, and the hilarious “I Don’t Want Santa to Come” by Jen Kwok based off the things her young son once said about his fear of Santa Claus (he’s “too loud” and “can eat cookies somewhere else!”).

Contemporary Originals

Jen’s original holiday song reminds us of so many others that have been written in (relatively) recent years, beginning with another Christmas queen, Mariah Carey. The next three are my picks, each of them featuring great guitar parts and odes to the love that this holiday is ultimately about: “Under the Tree” by Sam Palladio (of “Nashville” TV show fame), “Snowed In” by Mindy Smith (a lovelorn reminder that you don’t need much to make a perfect Christmas), and “North Pole” by Lori McKenna (a national tour down holiday memory lane). Read my review of the this stunning Christmas EP by Lori McKenna here.

If you know me (Hailey) at all, you know about my feelings for Lori McKenna. Similarly, if you know Jasmine, you know about Vienna Teng. She unknowingly helped mold Jasmine’s own belief that she could have a career as a songwriter and that her voice and stories deserved to be heard. Jasmine identifies with this song, “The Atheist Christmas Carol,” because she didn’t grow up religious, but found comfort in taking in the holiday season as a time to show up for and with people you love. I love the holidays for the same reasons. 

The New Year Songs

Every good holiday record or playlist flows straight into the New Year, so ours does too. We have to follow Vienna with her long-time collaborator Alex Wong with “January” by Alex’s duo with Amber Rubarth, The Paper Raincoats. It’s a rhythmic romp (“the bells!” screams Jasmine) that pairs well with another contemporary classic, “This Is the New Year” by A Great Big World.

We end the playlist with “What Are You Doing New Year’s Eve,” of course, from which there are so many great versions to choose. I went with Rufus Wainwright, because he can do no wrong, and because this piano will fill your heart no matter where you are.