I selected these songs from my playlist of top 100 faves for this Autumn (that list follows the MixTape below). I tried not to overrun the setlist with the same singer/songwriters, but Meg Washington and Taylor Swift both made too strong of an impression on me this year with their new releases.
I guess each person looking at this setlist will have different thoughts on what ties them all together. For me, it’s the story of my year leading up to Autumn. There’s definitely some sadness, but ultimately, it is uplifting with messages of hope, love, and light.
Enjoy… Perhaps some of these songs might be on your own Autumn ’25 playlist.
A-Side:
- 1. “With Plenty of Money & You” (Count Basie and Tony Bennett)
- 2. “Lazarus Drug” (Meg Washington)
- 3. “Death Wish” (Live from the O2 Arena) (Gracie Abrams)
- 4. “Emily, I’m Sorry” (boygenius)
- 5. “Eldest Daughter” (Taylor Swift)
- 6. “What’s Up” (Goodwerks & Ira Wolf)
- 7. “Vodka Cranberry” (Conan Gray)
- 8. “Too Good To Be True” (Kacey Musgraves)
- 9. “If You’re Hurting” (Trousdale)
- 10. “Don’t Put It All On Me” (Noah Cyrus & Fleet Foxes)
- 11. “the 1” (Taylor Swift)
- 12. “Dear Vincent” (Housman)
B-Side:
- 1. “The Fate Of Ophelia” (Taylor Swift)
- 2. “Dylan Thomas” (Better Oblivion Community Center)
- 3. “Everybody Wants To Rule The World” (Lorde)
- 4. “Night Changes” (Trousdale)
- 5. “Natural Beauty” (Meg Washington)
- 6. “Scott Street” (Phoebe Bridgers)
- 7. “Ordinary” (Alex Warren)
- 8. “Opalite” (Taylor Swift)
- 9. “Resonant Body” (Maggie Rogers)
- 10. “Fine” (Meg Washington)
- 11. “People Need A Melody” (The Head & The Heart)
- 12. “Three Little Birds” (Kacey Musgraves)
Here’s the link to the playlist on Apple Music if you care to give it a listen.
The Autumn Playlist: My Top 100
Now, about the rest of those songs on the list. For the last month, I’ve been building my annual Autumn Playlist. This year, I decided to limit it to 100 songs. I thought I was safe until Taylor Swift dropped Life of a Showgirl, and I had to make some tough choices about which tracks filled out those 100 songs.
I did it, though, and here they are, alphabetically by musician. The vibe is autumnal: a bit chill with an unsuspecting bite in the air here and there. You might also sense a mingling of hope and retreat (classic autumnal themes for me.….). Once again, here’s the link to this longer playlist on Apple Music.
I’ve added some necessary annotations along the way, some stories to share how they made the list.
Without further ado, here’s my Autumn ’25 Top 100 Songs, alpha by singer/songwriter:
ALEX WARREN
- “Ordinary”
AMY WINEHOUSE
- “Valerie” (Live, BBC recording)
BETTER OBLIVION COMMUNITY CENTER
- “Dylan Thomas”
I have to tell you, the first time I heard this song, I thought it was Michael Stipe and R.E.M. performing it. It’s a short, slightly upbeat song that sticks with me. It was a pleasant find…
BOYGENIUS
- “Me & My Dog”
- “Emily, I’m Sorry”
THE CACTUS BLOSSOMS
- “Got A Lotta Love”
CONAN GRAY
- “The Cut That Always Bleeds”
- “Vodka Cranberry”
I fell in love with Conan’s “Vodka” song the first time I heard it. Catchy tune with a deeper meaning. Nice.
COUNT BASIE & TONY BENNETT
- “With Plenty Of Money & You”
I first heard this song on Episode 9 of Seth Rogan’s The Studio on Apple TV. I can’t even tell you how many times I’ve watched it; it’s that good. Anyway, this song appears as Rogan and others enter CineCon in Vegas (“Vegas, baby!”), and it sets the tone for an outrageous story where everything goes wrong in the most hilarious way. It’s perfect for this playlist.
FRUIT BATS
- “Today”
GOODWERKS & IRA WOLF
- “What’ Up”
Great cover of the 4 Non Blondes hit.
GRACIE ABRAMS
- “Block Me Out”
- “Death Wish” (Live from the O2 Arena)
- “I Miss You, I’m Sorry”
- “Us” (Featuring Taylor Swift)
- “Close To You”
THE HEAD AND THE HEART
- “People Need A Melody”
HOLLY HUMBERSTONE
- “Haunted House”
HOUSMAN
- “Dear Vincent (Letters to van Gogh)”
HOZIER AND BRANDI CARLILE
- “Damage Gets Done”
ILSEY
- “Yellow Roses”
ISRAEL KAMAKAWIWO’OLE
- “Somewhere Over The Rainbow/What A Wonderful World”
JAMES TAYLOR
- “Never Die Young” (Live at Frederick P. Rose Hall)
- “September Grass”
- “October Road”
KACEY MUSGRAVES
- “Too Good To Be True”
- “Golden Hour”
- “Rainbow”
- “Keep Lookin’ Up”
- “Three Little Birds”
LAINEY WILSON
- “Out of Oklahoma”
LANA DEL REY
- “Bluebird”
- “Let The Light In” (Featuring Father John Misty)
- “Love”
LINKIN PARK
- “One More Light”
LORDE
- “Everybody Wants To Rule The World”
- “Royals”
- “Stoned At The Nail Salon”
THE LUMINEERS
- “Ophelia’
- “Where The Skies Are Blue”
- “Nobody Knows”
MAGGIE ROGERS
- “Resonant Body”
MEG WASHINGTON
- “Lazarus Drug”
- “Gem”
- “Shangri-La”
- “Golden Orb Blues” (Featuring Kevin Morby)
- “Natural Beauty”
- “Starlife”
- “Honeysuckle Island”
- “Fine” (Featuring Paul Kelly)
I first learned of Meg from the hit Disney show, Bluey. In Season 3, toward the end of “The Sign” episode, “Lazarus Drug” plays as Bluey contemplates their future in a new home. Now, the song is seemingly about reversing opioid overdoses. Strange choice for a kids’ show, right? But it works, and I fell in love with Meg’s music. Well, earlier this year, she dropped her latest album, Gem, and it is exactly that: A Gem.
MILEY CYRUS
- “Flowers” (Demo)
MYLES SMITH
- “Stargazing”
NOAH CYRUS
- “Hardest Part”
- “I Burned LA Down”
NOAH CYRUS AND FLEET FOXES
- “Don’t Put It All On Me”
NOAH KAHAN
- “Orange Juice”
NOAH KAHAN AND KACEY MUSGRAVES
- “She Calls Me Back”
P.J. HARDING AND NOAH CYRUS
- “Dear August”
THE PAPER KITES
- “When The Lavender Blooms”
THE PAPER KITES AND LUCY ROSE
- “For All You Give”
PASSENGER
- “Sword And The Stone” (Acoustic)
PHOEBE BRIDGERS
- “Scott Street”
SASHA ALEX SLOAN
- “Dancing With Your Ghost”
STEPHEN SANCHEZ AND EM BEIHOLD
- “Until I Found You”
STEVIE NICKS AND LINDSEY BUCKINGHAM
- “Twisted”
TAYLOR SWIFT
- “the 1”
- “Invisible String”
- “Betty”
- “Exile” (Featuring Ben Iver)
- “Mirrorball”
- “The Fate Of Ophelia”
- “Elizabeth Taylor”
- “Opalite”
- “Eldest Daughter”
- “Cancelled!”
- “The Life Of A Showgirl” (Featuring Sabrina Carpenter)
- “You Need To Calm Down”
- “Snow On The Beach” (Featuring Lana Del Rey)
- “Anti-Hero”
- “Would’ve, Could’ve, Should’ve”
- “Nothing New” (Taylor’s Version) (Feturing Phoebe Bridgers)
- “Begin Again” (Taylor’s Version)
- “Dear John” (Taylor’s Version)
- “Fortnight” (Featuring Post Malone)
- “The Tortured Poets Department”
- “Fresh Out The Slammer”
- “Clara Bow”
- “The Prophecy”
- “The Manuscript”
When Life Of A Showgirl dropped at 12:12 a.m. Friday, October 3, I immediately loved five tracks: “Fate of Ophelia,” “Opalite,” “Eldest Daughter,” “Cancelled,” and “Life Of A Showgirl.” The following morning, “Elizabeth Arthur” grew on me as well. Don’t get me wrong – I love the whole album. If I had to pick the top faves, these are the six I’m going with.
THE WAILIN’ JENNYS
- “Light Of A Clear Blue Morning”
TISH MELTON
- “Long Drive” (Featuring Brandi Carlile)
TROUSDALE
- “Happy Anymore”
- “Movie Star”
- “If You’re Hurting”
- “Night Changes”
- “What Could I Say”
VANCE JOY
- “Riptide”
WILD RIVERS
- “Thinking ‘Bout Love”
WILDERADO, KEN POMEROY, AND JAMES MCALISTER
- “Wall Of Death”
I’m curious about how many of these songs would make your autumnal list. Drop me a note (or a comment) and let me know!
Rus VanWestervelt 
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