Happy merry jolly melancholy Christmas — 15+ hours of musical holiday cheer

Kay Flewelling
5 min readNov 29, 2020
Merry making since 1993

I am an unabashed fan of Christmas/winter/holiday music. I have a thing for listening to sleigh bells chime and singing about snow amidst the colorfully lit palm trees that adorn my neighborhood. While living abroad, I started a tradition of selecting my favorite Christmas songs and arranging them into a mix to share a magical emotional musical journey with my beloved at a distance. Twenty-twenty-three marks the end of a decade of Christmas mix-making, and each year dives deeper and deeper into the vast holiday song vault to emerge with some unique and delightful mixes.

2023 — Slightly silly singalong songs for everyone (but mostly young’uns)

A collection of slightly sillier songs for kids & grown-ups who don’t take themselves too seriously

Highlights & delights:

  • Many of these songs were piloted on my five-year-old child during our Thanksgiving road trip. He was delighted by the old, silly classics like “I Want a Hippopotamus for Christmas” (1953) and “I’m Getting Nuttin for Christmas” (1955).
  • I enjoyed reaching back into the recesses of my own childhood for songs from Raffi’s Christmas Album (1983), Sharon, Lois & Bram (1993), and even Psalty the Song Book (1982), which honestly has a rocking Christmas medleys that is well worth its 7+ minute runtime.
  • Sufjan Stevens is a grown-up who does not take himself too seriously, and I have loved his prolific Christmas recordings, but sometimes they are harder to mix with the classics. In this mix, “We Need a Little Christmas” (2012) and “Come on! Let’s Boogey to the Elf Dance” (2006) are right at home.

2022 — In love at Christmastime

Highlights & delights:

  • Joanie Sommer’s “Baby It’s Cold Outside” (1963) is a gorgeous version of this classic song, and it’s only got the woman’s side of things to keep things feeling a lot less creepy.
  • Each year, I enjoy inviting a non-Christmas song into the Christmas genre, and this year, I invited two: Hayden Calnin’s “Warm with You” (2019) and Kina Grannis and Jome’s “Gold” (2021). The first time I heard “Gold,” I knew it would become Christmas cannon. I love its hopefulness — “built and broken after a thousand moments, for giving in, an opening to let it begin” — an invitation to let merriness win.
  • This mix is replete with the jazz greats (Ella, Billie, Nat, Louis, June and more), but Peggy Lee’s “Christmas Waltz” (1960) is the one that best captures the spirit of a mix full of Christmas love songs — “it’s that time of year when the world falls in love.”

2021 —A Jazzy Soulful Christmas

Highlights & delights:

2020 — Happy merry jolly melancholy Christmas

A little merry and a little melancholy to brighten up these darker days.

Highlights & delights:

  • Quintessential Christmas bells and António Calvário singing “O que quer dizer Natal/What Christmas means” (1967), a Portuguese classic that manages to translate holiday cheer into any language
  • Everything about soul singer Nuela Charles’s rendition of “Angels we have heard on high” and Guatemalan singer-songwriter Gaby Moreno’s rendition of “December”
  • The line “Merry Christmas, babe, I hope we’ll make it through” from Mt. Joy, which conveys exactly my feelings about this holiday season

2019 — Eclectic Christmas

Another mostly indie Christmas mix with some old favorites and some new tunes. Get jolly why doncha.

Highlights & delights:

  • Aloe Blacc’s scat singing during his rendition of “Santa Claus Is Comin’ to Town” is a perfect example of how to breathe new joyful life into old radio classics and I’m here for it
  • I love, love, love Ariana Grande’s sweet original ukulele song “Winter Things” (2015) about harnessing the power of her imagination to celebrate Christmas in Los Angeles — even though this sun is blasting we can be wherever if we visualize
  • Nataly Dawn is perhaps my favorite contemporary artist in the genre of Christmas music (her voice is practically as sweet as Christmas bell), and her French cover of “All I Want for Christmas Is You” with Cyrille Aimée makes me so happy

2018 — Mostly Instrumental Christmas

Sometimes it’s nice to let the music speak the magic.

Highlights & delights:

  • Joan Baez released a Christmas album in 1966, and her rendition of “Bring a Torch, Jeannette, Isabella” is 38-seconds of perfection
  • Guitar virtuoso Fareed Haque’s brilliant cover of “You’re a Mean One, Mr. Grinch”
  • Honestly, I think I may have made this entire mix mostly instrumental so that I could find a home for the super weird and super wonderful Christmas music by The Flaming Lips, which breaks all my mixing rules by showing up three times in 80 minutes to excite and delight you

2017 — Indie Christmas Cheer

Annual mix to celebrate this cheery time of year, indie artists old & new, a soft sort of not overplayed pop kind of vibe.

Highlights & delights:

  • Australian singer-songwriter Vera Blue covers Dean Martin’s (1967) “A Winter Romance” and makes it feel completely timeless, contemporary, and magical and it has become one of my favorite holiday songs
  • Fiona Bevan’s original song “They Sang Silent Night” (2014) haunts and enchants with its storytelling about Christmas at wartime and I love it so much — let’s sing it again, all together and send a love to end all wars, peace time forevermore

2016 — No Christmas Like a Soul Christmas

Soul music to groove to at Christmastime.

Highlights & delights:

  • This whole mix is a delight, inspired by a colleague at my school who realized I’d never really heard Donny Hathaway’s classic “This Christmas” — so I went on a deep dive into soul Christmas and it’s all classic, just not what was on regular rotation in my house growing up
  • Sister Rosetta Tharpe’s rendition of “O Little Town of Bethlehem” is so gorgeous
  • The titular track comes from Count Sidney & His Dukes “Soul Christmas”

2015 — Let’s Get Cozy

A wintery mix of holiday songs with varying familiarity.

Highlights & delights:

  • The opening track, “Mvmt IV ‘Every Bell on Earth Will Ring’” by The Oh Hellos is a gorgeous medley (all of their Christmas songs are entirely beautiful)
  • There’s some really lovely indie gems on this mix: “Christmas TV” by Slow Club, “Let’s Get Cozy” by Three Day Threshold & Summer Villains, and “Christmas Wrapping” by The Waitresses

2014 — The best of new and old Christmas

First annual Christmas mix with contemporary cheer — for when you want a little bit of everything and you don’t care who knows it.

Highlights & delights:

  • The opening track “Maybe This Christmas” by Ron Sexsmith is a bit of an inspiration for these mixes: when I was in college, I came across the album Maybe This Christmas which featured many of my favorite artists covering old Christmas songs, and it’s in that spirit that I created my own
  • I was watching a lot of Nashville during this year, so the Nashville cast shows up a lot on this mix. While they are not acclaimed singers, their renditions of old favorites are kind of wonderful
  • “Sister Winter” by Sufjan Stevens is my absolute favorite track from his abundant collection of holiday songs

Playlist to inspire cheer.

All of the mixes, plus three of my fav Christmas albums, for over 11 hours of holiday fun.

My all-time favorite Christmas album is a compilation from Bath & Body Works called “Let It Snow” (1995) and the first 15 tracks from this playlist are from that album. The first notes from Nat King Cole’s “The Christmas Song” are everything.

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Kay Flewelling

I am an artist, writer, thinker, and educator. I teach in the San Diego Unified School District and at the University of San Diego.