This playlist is a small winter world I wanted to share. It begins with familiar warmth, but it grows and shifts the way the holidays do when you mix memory, family, late nights, and a bit of rebellion. I hope you find something new to love in here, and that it keeps you company while you wrap presents, warm the house, or gather with people you care about.
1. Snow (feat. Trudy Stevens) - Bing Crosby, Peggy Lee, and Danny Kaye
This is the doorway into the playlist, a scene setter full of vintage charm. It invites you in with a familiar glow before anything unexpected happens. It also happens to be from one of my favorite musicals.
2. White Christmas -
The Drifters
A version that’s both classic and full of personality. It keeps the nostalgia but adds a gentle sway that starts to loosen the edges. "Merry Christmas, ya filthy animal!"
3. God Rest Ye Merry Gents - Sharon and The Dap-Kings
Here is the first hint that the playlist has its own point of view. Sharon Jones and the Dap-Kings turn a centuries-old melody into something alive and funky. That brass! It honors tradition but refuses to stay still.
4. Cool Yule (feat. The Commanders) - Louis Armstrong
Armstrong brings a wink and a grin without ever crossing into kitsch. It lifts the mood while keeping the brass-polished elegance intact. Also, Louis is one of my favorite artist, so I refuse to pass up an opportunity to share him.
5. Jingle Bells, Pt. 1 -
Pastor T. L. Barrett and The Youth for Christ Choir
This track is another new take on an old favorite and it fills the room with joy that feels homemade rather than commercial. It’s a reminder that holiday music can be spirited without being sugary.
6. We Three Kings -
Dave Brubeck
Brubeck brings a cool sense of space to a well-traveled carol. The trio stretches it into something contemplative and quietly modern.
7. Christmas Time Is Here - Khruangbin
Khruangbin takes a childhood classic and gives it a soft, floating atmosphere. It hints at future edges in the playlist while keeping the moment serene.
8. The Little Drummer Boy - Lou Rawls
There are so many versions of this song, Lou Rawls turns it into a slow, soulful night walk. It’s a familiar story told with a deeper, velvet tone.
9. You'd Be So Nice To Come Home To (Live, 1958) - Sarah Vaughan
Not a Christmas song, but it feels like returning to warmth after cold air. Vaughan’s voice creates its own fireplace.
10. Purple Snowflakes - Marvin Gaye
Marvin Gaye adds dreamlike color to winter. It’s a small piece of Motown magic that feels like it drifts down from above.
11. The Nutcracker Suite - Les Brown and His Band of Renown
A big band take on Tchaikovsky that balances showmanship with real musical craft. It keeps the energy lifted without breaking the mood.
12. Here Comes Santa Claus - Ramsey Lewis Trio
Ramsey Lewis keeps things light and playful. It’s a breeze that carries you forward with a smile.
13. Greensleeves (Take 4) -
John Coltrane
Coltrane turns an old melody into something spacious and searching. It deepens the playlist and gives it a thoughtful center.
14. Peces en el Rio - Gaby Moreno
A song from childhood Christmases, carried into a new era with tender, continental instrumentation. It bridges languages and traditions while adding a new jazzy swing.
15. Snowfall - Ahmad Jamal Trio
A quiet, drifting moment. Jamal’s touch feels like snow landing on still streets.
16. Gee Baby (Ain't I Good to You) - Peggy Lee
Warm, intimate, and gently romantic. It’s a moment to breathe before the playlist shifts its energy.
17. Christmas Every Day -
The Miracles
A cheerful lift that keeps things soulful. It feels like a last toast before the night gets louder.
18. I Wish It Was Christmas Today -
Julian Casablancas
The true turning point into the rock side of the playlist. Originally a song on SNL, this track is loose, messy, and full of heart.
19. Vegetarian Christmas - Feet
A playful, scrappy holiday anthem. It brings humor without cynicism and keeps the energy rolling. Its just so charming and doesn’t feel overly preachy (and the Linda McCartney reference always reminds me of the Simpsons episode where Lisa decides to become a vegetarian).
20. Fairytale of New York (Edit) - The Pogues
Raw and heartfelt. It’s a winter story with grit, melancholy, and a surprising amount of tenderness. *this version also omits the unfortunate slur found in the original
21. Nothing for Me - The Muffs
A burst of punk honesty that feels strangely fitting near the end of a holiday playlist. It clears the air in the best way.
22. Santa Claus Wants Some Loving - Albert King
A sly, warm finish. Albert King sends the listener out with a grin and a low blues groove, closing the journey on a relaxed note.