You may notice a certain theme to the end of this playlist. That theme is I wanted it to feel like Christmas this year, and I successfully achieved that through musical saturation. Made more effective because, after years of being A Choir Kid, it’s not just hearing Christmas music that makes it feel like Christmastime to me, it’s singing it—and thus, lots of choral/a cappella versions.
As usual, you can listen to the whole playlist here or see the track list and commentary below. (I’m trying something a little different with the commentary formatting this time—hopefully it’s a little easier to scan through.)
Oklahoma Smokeshow – Zach Bryan on Summertime Blues – EP
Hotel Bible – Max McNown on Night Diving
Medusa – Cameron Whitcomb on Medusa – Single
Options – Cameron Whitcomb on Clean Country 2025
Azalea Place – Max McNown on Night Diving
St. Helens Alpenglow – Max McNown on St. Helens Alpenglow – Single
Flicker – Yoste on Flicker – Single
Livin’ Missing You – Hayden Blount on Livin’ Missing You – Single
American Trail – Dylan Gossett on Westward
Normal Day – Brendan Walter on Normal Day – Single
Sea Shanty Medley – Home Free on Sea Shanty Medley – Single
The Barn – Landon Smith on The Barn – Single
Loud and Heavy – Cody Jinks on Adobe Sessions
Did What You Did – Noah Brigden on Bad Habits – EP
Life’s Worth Living – Nick Folwarczny on Life’s Worth Living – Single
Dale Dickens (RIP) – Cooper Alan on Dale Dickens (RIP) – Single
Cold Shoulder – Zach John King on Slow Down – EP
Life Behind Bars – Zach John King & Bayker Blankenship on Life Behind Bars – Single
Man of the Year – Sam Barber on Man of the Year – Single
Bowery (feat. Kings of Leon) – Zach Bryan on Bowery (feat. Kings of Leon) – Single
HIGHWAY KIND – Fabrizio on HIGHWAY KIND – Single
Space – Zach John King on Space – Single
Dust and Smoke – Sam Barber on Music for the Soul
808 HYMN – Erin LeCount on 808 HYMN – Single
Gun To My Head – HARDY on COUNTRY! COUNTRY!
Music for the Soul – Sam Barber on Music for the Soul
Luckiest Man Alive – HARDY on COUNTRY! COUNTRY!
American Vintage – Aidan Canfield on American Vintage – Single
Cheap Shots – Ian Harrison on Cheap Shots – Single
The Wreck of the Edmund Fitzgerald – Home Free on Challenge the Sea
Bedrooms In The Sky – HARDY & Stephen Wilson Jr. on COUNTRY! COUNTRY!
Lose A Friend – Evan Honer on Everything I Wanted
The Gold – Manchester Orchestra on A Black Mile To The Surface
Later Tonight – Josh Ross on Later Tonight
Old White Lincoln – The Gaslight Anthem on The ’59 Sound
Storytime – Majik on Blood, Sweat & Tears
Road to Gold – Luke Beling on The Good Side of Somewhere – EP
Oh! The Anxiety – Joe Jordan on Oh! The Anxiety – EP
Baptized By Rain – Dylan Gossett on Westward
Drift Away – Orville Peck on Appaloosa
Leave Her Johnny – Home Free on Challenge the Sea
nah – Khalid on after the sun goes down
Undone (The Bonfire Sessions) – Sons of Habit on The Sticks (The Bonfire Sessions) – EP
Wish You Well – Vincent Mason on There I Go
Facilita – Fred again.., Caribou & Menor Teteu on Facilita – Single
Hardwired – Fabrizio on Hardwired – Single
Lonely Man (One Take Acoustic) – Cody Jinks on Lonely Man (One Take Acoustic) – Single
Skull and Bones (2025 Version) – Home Free on Challenge the Sea
Berghain – ROSALÍA, Björk & Yves Tumor on LUX
Something Wicked This Way Comes – Cody Jinks on In My Blood
The Parting Glass – Home Free on Challenge the Sea
Foolish Pride – Slater Nalley on Foolish Pride – Single
My Side Of Town – Josh Ross on Later Tonight
Bonnie Ship the Diamond – Home Free on Challenge the Sea
HARDSTYLE 2 – Fred again.., KETTAMA & Shady Nasty on HARDSTYLE 2 – Single
Mingulay Boat Song – Home Free on Challenge the Sea
Santiana – Home Free on Challenge the Sea
Bottled Up Inside – Harrison Storm on Empty Garden
Holiday Road – Kesha on Holiday Road – Single
Shovel – Tyler Nance on Shovel – Single
Sunflower – Amber Run on Sunflower – Single
Roots – Cooper Alan on Winston – Salem
Challenge the Sea (feat. The Longest Johns) – Home Free on Challenge the Sea
WTF (the f**k) – Gracie and Rachel & Elliot Moss on WTF (the f**k) – Single
Human – Brandi Carlile on Returning To Myself
Got It All Wrong – Peech. on Small Town America (Vol. 1) – EP
Atchafalaya (feat. Noah Cyrus) – Orville Peck on Appaloosa
My Side of the Mountain – Orville Peck on Appaloosa
O Come, All Ye Faithful – Pentatonix on A Pentatonix Christmas
God Rest Ye Merry Gentlemen – Pentatonix on A Pentatonix Christmas
Coventry Carol – Pentatonix on A Pentatonix Christmas
I think this one is my favorite Christmas song this year, which is a bit odd, but boy, do I have fun listening to some of the harmonies. Those open fifths, mmmmm.
Hark! The Herald Angels Sing – Pentatonix on That’s Christmas To Me
White Winter Hymnal – Pentatonix on That’s Christmas To Me
That’s Christmas To Me – Pentatonix on That’s Christmas To Me
Mary, Did You Know? – Pentatonix on That’s Christmas To Me
The First Noel – Pentatonix on That’s Christmas to Me: Deluxe Tracks – EP
Little Drummer Boy – Pentatonix on The Greatest Christmas Hits
Carol of the Bells – Pentatonix on The Greatest Christmas Hits
Deck The Halls – Pentatonix on The Greatest Christmas Hits
J&L – Medium Build on takeaways
A quick break from the Christmas vibes here, and this one is, lyrically, something of a gut-punch to me.
Pipe Dream – Brendan Walter on Disappearing Days
I enjoyed the cinematography of the music video for this one.
Blueneck (Acoustic) – Chris Housman on Blueneck (Acoustic) – Single
Honestly, I think I added this originally because I was conflating with the artist Blueneck, who make music that sounds like being alone in the depths of winter, and have been known to show up in my December playlists. Instead, I’ve got this piece, which feels like… an earnest take on Bo Burnham’s Pandering.
O Come, All Ye Faithful – Home Free on Any Kind of Christmas
O’ Holy Night – Home Free on Full Of Cheer (Deluxe)
White Sand Christmas – Jake Slaton on White Sand Christmas – Single
A non-traditional insertion, but I’ve been enjoying it.
Do You Hear What I Hear? – Home Free on Full Of Cheer (Deluxe)
Silver Bells – Pentatonix on Christmas in the City
73 Fair – Noah James on 73 Fair – Single
Talk to You – Sam Fender & Elton John on People Watching (Deluxe Edition)
Similar to J&L above in terms of hitting too hard.