Playlist of the Month: December 2025

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

Space in My Heart (Original Version) – Enrique Iglesias on Space in My Heart (Original Version) – 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

CATHEDRAL. – Kesha on .

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

We’re Onto Something (feat. Zach Bryan) – Kings of Leon on We’re Onto Something (feat. Zach Bryan) – Single

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

Wave – Yoste on Wave – 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

Magnolias – ROSALÍA on LUX

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

Te Amo – Rihanna on Rated R

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.

The Hanging Tree – James Newton Howard on The Hunger Games – Mockingjay Pt. 1 (Original Motin Picture Score)