Charlie Kaplan’s Tom Petty 101 Playlist

Following the release of his new LP Country Life in America, the songwriter shares his journey to Petty fandom before detailing 10 of the 115 songs he considers the late musician’s best.

Charlie Kaplan’s Tom Petty 101 Playlist

Following the release of his new LP Country Life in America, the songwriter shares his journey to Petty fandom before detailing 10 of the 115 songs he considers the late musician’s best.

Words: Charlie Kaplan

Photo: Sam Shapiro

September 18, 2023

You know how in a Warner Brothers cartoon, a piano would occasionally fall on an animated character? And when they crawled out through the lid, with the strings curled up and notes still ringing in the air, they’d reveal through a woozy smile that their teeth had been replaced by its black-and-white keys? This is how an artist hits me sometimes. It was D’Angelo, in my late teens, who I spooled endless hours for, trawling the OkayPlayer boards looking for a voluble missive from Questlove, an old tour bootleg, or a leaked demo from an album that seemed then like it might never arrive. Later it was Joni Mitchell, in whose backseat I silently sat as she piloted a solo flight across arid landscapes of heartbreak and soul-searching. 

And then, in May 2022, it was Tom Petty. I hadn’t paid him too much mind prior, outside “American Girl” and “Don’t Do Me Like That.” I’d once given Damn the Torpedoes a try, but this time it shattered me. A fixation set in and persisted for a full six months until I emerged in November, keys dangling from my gums, having listened multiple times to every album and compilation and live album he ever made and boiling it down into a single, highly economical seven-and-a-half-hour-playlist of what I consider to be the cream of the crop.

Winnowing an artist’s discography down to around the length of a workday sounds like an absurd joke. My prompt wasn’t to find the 115 best Petty songs, or to make a primer for my past self, but rather to save any song that felt like I’d want to come back to it sometime. In so doing, I demonstrated to myself the feat his career represented, in all its scale and varied modes. There are the shimmering, scintillating rock songs where the melange of jangling, Byrds-like electric 12-string guitar and shining organ feel like falling in love; the buck-toothed country tunes bred in Gainesville; the shrouded confessionals revealing darkness his radio repertoire belied. Before my revelation, I’d disregarded Tom Petty as pablum; once he hit me, I was awash in awe at how hard it is to say it as straight as he did.

I named those seven and a half hours of playlist “My Middle Name is Earl,” not as a tribute to the Jason Lee sitcom, but after a supremely droll lyric in the Full Moon Fever album cut “A Mind with a Heart of Its Own.” It’s an uncharacteristically oblique song—is it about his parents? An old flame? He usually tells you, but not now—that boils down to, “Wherever you go, there you are.” But here’s how Petty says it:

Well I been to Brooker, and I been to Micanopy
I been to St. Louis too, I been all around the world
I’ve been over to your house and you’ve been over sometimes to my house
I’ve slept in your treehouse, my middle name is Earl

When you first hear it, it sounds non-sequitur. But it’s his way of peering out to remind you: You already know me. We go back. This familiarity is no illusion.

I wrote my album Country Life in America before falling for Petty, but he hit me like a falling piano soon after I started recording it. Looking to his catalog carried me through to the end of making it and made me buy an electric 12-string guitar. In that way I feel like ultimately he became its patron saint. A few nights ago, a drummer and I were working out some of the songs on this album and he commented, “I take to your songs really easily.” I wanted to wink at heaven.

I’d like you to benefit from the fruits of my labor, so here are 10 of those 115. Not the best ones, not the rarest ones, just 10 that stick with me and whose familiarity persists.

“Keep a Little Soul” (Outtake)
A classic example of forgetting something better most songwriters ever thought of, this one got pulled from Long After Dark despite carrying its most enduring and universal message: Don’t lose your soul, chase your dreams, don’t be afraid to live what you believe.

“The Wrong Thing to Do”
Early on, Petty was in a band called Mudcrutch along with future Heartbreakers Mike Campbell and Benmont Tench. He got the band back together in 2007 and rode in on this song, which, after inhaling his biography through documentaries and endless articles, read like his Da Vinci code for me. It’s a fearless disclosure of dysfunction, both hopeless and carefree. It gives me the visceral sensation that this guy knew exactly what screwed him up, had no idea how to spare himself from it, and so fell for its abandon.

“Shadow of a Doubt (Complex Kid)”
I relish a purely observational love song. Throughout its narrative, Petty doesn’t really say a thing to his romantic interest. He just puzzles at her and her idiosyncrasies, privately chewing on her oddities. She sings in French in her sleep, but doesn’t remember it when she wakes up. Petty’s fascination with her keeps him thinking of her, waiting around for her to get off work, singing about her. It reminded me of The Band on “Up on Cripple Creek”: “My Bessie can’t be beat.”

“Harry Green”
It could be fiction or autobiography, it’s hard to tell. The details are both prosaic and fantastical: The song’s subject emerges in the most familiar of circumstances—Spanish class—but possesses supernatural qualities: strong, tall, brave enough to protect little needle-necked Tom from menacing rednecks. But homophobia eats even Green away from the inside, an early lesson in the unrelenting cruelty and unfairness of life.

“Zombie Zoo”
I’ve expressed my love of this song to friends before and been met with quizzical looks. It’s so funny to me. At 39 when this album came out, Petty must have started to feel like an old dude. This song paints him, shaded and stoned, peering at the teenaged scenesters haunting his adopted home of Los Angeles, and muttering, “Man… I dunno…” I especially like when he jokes the little twerps “look like Boris Karloff” and then, realizing they were born after Karloff died, concedes, “...and you don’t even care.”

A lot of people end the Petty story after Wildflowers, and I get it. In the 1970s and ’80s he achieved legendary rock god status and, to some degree, burned out. But then he had a second act in the late ’80s and early ’90s, spinning out many of the songs he’s best known for, like “Free Fallin’” and “Mary Jane’s Last Dance.” He got on Mount Rushmore with The Traveling Wilburys. After that era I found a quieter corpus of music, less trumpeted by his devotees, but rendered in totally different tones. This one struck me early on in my trek across the discography: It’s desperate and triumphant, huge and private.

“You Come Through” (Demo)
This is such a weird one, I love it. It’s funky and straight, not really like any other groove in his songbook. He plays around with his vocal range and Lenny Kravitz holds him down with excellent backing vocals. It doesn’t seem like a Petty song, but it works so well.

“Girl on LSD”
There’s Bogdanovich’s four-hour Petty doc; that’s great. But there’s also the more recent Wildflowers doc Somewhere You Feel Free, which presents this outtake as an example of his natural, improvisatory humor. I like it in no small part because it does feel like he’s making it up right there to get a laugh from the assembled, like he could play it late at a party and everyone would enjoy it.

“Baby’s a Rock ’n’ Roller”
I had that breakthrough with Damn the Torpedoes and knew immediately I needed to listen to every album. I moved to the self-titled debut and loved it. Then I got to this one, didn’t recognize any singles, and wondered if this would be when the wheels fell off. Instead, it presented even more evidence that I was onto something. This is the type of song you can put on loud in a car full of people who have never heard it and they’ll feel it, but when you get back and read the lyrics—“dental assistant?”—you’ll still get a sense of how funny and odd this guy was.

“Don’t Fade on Me”
It sounds like it’s in one of those dark Northern English tunings that Nick Drake or Jimmy Page used. Wildflowers is such a profoundly sad album, but it only occasionally wears its despair on its sleeve like it does here. There’s no glimpse of the crooked smile or glinting eye that defined Petty’s charm here, just nakedness and desperation.