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Adam Wilson’s Book Notes music playlist for his novel Fail Sons

“Scott Platt, the narrator of Fail Sons, is an unemployed forty-year-old Brooklynite who spent fifteen years editing the culture section at a glossy magazine before the decline of print journalism ended his career. In other words, he’s a man with opinions about music.”

In the Book Notes series, authors create and discuss a music playlist that relates in some way to their recently published book.

Previous contributors include Jesmyn Ward, Lauren Groff, Bret Easton Ellis, Celeste Ng, T.C. Boyle, Dana Spiotta, Hanif Abdurraqib, Andrew Sean Greer, Roxane Gay, and many others.

Adam Wilson’s Fail Sons is one of the year’s funniest and heartfelt novels, the brotherly road trip story (accompanied by their cryonically-preserved (and thawing) father you didn’t know you have to read.

Publishers Weekly wrote of the book:

“Wilson hits all the right notes in this dynamic dark comedy about grief and hope. Readers will enjoy the ride.”

In his own words, here is Adam Wilson’s Book Notes music playlist for his novel Fail Sons:

Scott Platt, the narrator of Fail Sons, is an unemployed forty-year-old Brooklynite who spent fifteen years editing the culture section at a glossy magazine before the decline of print journalism ended his career. In other words, he’s a man with opinions about music. You will find those opinions scattered throughout the novel—Scott opines on Pavement, Taylor Swift, and all points in between. He wonders why Kenny Rogers’s “The Gambler” would play in a casino since it encourages prudence, and he makes a case for Miley Cyrus’s “Party in the USA” being the greatest pop song of the twenty-first century. He worries that recommendation algorithms have made guys like him obsolete (his wife reassures him he was already obsolete.) 

As Scott’s takes on these songs appear in the book, I thought I’d use this space to discuss some that don’t, but that do feel relevant to it, both personally and thematically. Fail Sons is a book about aging and mortality; fathers, sons, and brothers; failure and grief. These songs have guided my understanding of these subjects as I’ve dealt with them in both my writing and my life.

Drive-By Truckers – “Outfit”

I didn’t cry for roughly a decade. Then I switched from Prozac to Wellbutrin, and proceeded to weep at every father/son scene in every movie ever made. A particular one that gets me is Alec Baldwin teaching his son, Dildo, to tie a tie in the Farrelly Brothers classic, Outside Providence.

Listening to music can be a very emotional for me, but for whatever reason, it doesn’t make me tear up like films do. There are exactly two exceptions, and “Outfit” is one of them. Actually, there are three exceptions if you count Bruce Springsteen’s spoken intro to “The River” on Live 1975-85, an anecdote about Bruce, his dad, and the Vietnam War that I sometimes listen to while walking the Prospect Park loop; if you see a middle-aged bald man crying into his hands as he stumbles down the track, wave hello! (that live version of “The River” is pretty great too.)

Jason Isbell wrote “Outfit” at twenty-two after being invited to join Drive-by Truckers. In it, he sings from the perspective of his own dad—a house painter—giving advice to his son before he heads out on tour. The empathy with which Isbell inhabits his father’s perspective elevates what might feel like a gimmick into something profoundly moving, the rust belt response to Springsteen’s “Independence Day” we didn’t we know we needed. The narrator counsels young Jason to use common sense (“steer clear of the needle”) and remember his roots (“don’t sing with a fake British accent.”) He describes his own abandoned dreams of economic mobility, underlined by his hopes for a bigger life for his son. The kicker cues the waterworks: “Don’t tell them you’re bigger than Jesus…don’t give it away.”

Bruce Springsteen – “Highway Patrolman”

I still haven’t watched that Springsteen biopic with the guy from The Bear, and Nebraska is not even in my top five Bruce records, but I did read Warren Zanes’ fantastic book that inspired the movie, and I do love some songs from that album. My favorite is “Highway Patrolman,” a devastating ballad about siblings and mercy. A guy kills someone in a bar fight, and his brother—a cop—chases him to the Canadian border, only to let him go. The song ends with the narrator watching his brother’s taillights recede into darkness. It reminds me of Andre Dubus’s short story, “A Father’s Story,” in which a devout Catholic helps his daughter dispose of a body, an act the narrator justifies to God by explaining that since God never had a daughter, only a son, He has no right to judge.

Michael Ian Cummings – “Oldest Troubles”

I’ve been listening to Michael’s music since we were teenagers in suburban Massachusetts, and this title track from his first solo EP is my favorite thing he’s ever done. What the singer’s “oldest troubles” are is never specified—all we know is that he must face them—and the lack of specificity makes the song feel universal. Like Fail Sons, its theme is early onset middle-age (In Fail Sons, Scott prefers to call it “the slow denouement of youth”) and how alienating it can be when the rest of your cohort seems to have advanced in their lives and careers in ways that you haven’t. “Work is hard if you hate it,” may be one of the great opening lines of all-time. 

Joni Mitchell – “Little Green”

There’s a moment in every music fan’s life when they must face the fact that everyone loves Blue—it is not yours alone—and that, in fact, everyone else’s favorite song on itis “A Case of You” too.  But you know what else is a perfect song? Well, all of them, but especially “Little Green.” The line “child with a child pretending” used to repeat in my head when I’d push my older son’s stroller around Brooklyn. I was thirty-six when he was born, and like Scott in Fail Sons, I was emerging from a rather protracted adolescence. In the old days, a man might have been to war and back by that age! In some sense, Fail Sons is a book about Millennials having to accept that we’re no longer children pretending to be adults—we’re just adults now, full stop.  

Pinegrove – “Old Friends”

Apparently the theme of this playlist is songs that destroy me. “Old Friends” does it in a single line: “I saw Leah on the bus a few months ago/I saw some old friends at her funeral.” What an incredible distillation of the swiftness and brutality of time!

The years I spent writing Fail Sons involved a not insignificant measure of grief, including the sudden and unexpected passing of my dear friend, Bret. I always associate this band with him because of a photo in which he and I are jamming out a different Pinegrove song, “Angelina,” at a dingy practice space in Gowanus. I’m on guitar, Bret is on drums, and I can tell what we’re playing because there’s a capo on the sixth fret and my fingers are formed in a C add 9 chord. That photo hung framed above my desk while I was writing the book.

Prince – “Little Red Corvette”

When children are very young they have to listen to the music you choose. Later, they develop their own tastes, and car rides become occasions for the Encanto and K-Pop Demon Hunters soundtracks. I was in a big Prince phase when my older son was a toddler, and he loved this song. We spent some long mornings listening to it on repeat, and I’ll forever associate it with the specific joy of watching someone who has only just learned to walk try to dance. Fail Sons is a death-haunted book—it’s literally about two guys driving around with their dad’s corpse—but it is also, I hope, a book that comes down on the side of life. Nothing brings both the fragility and beauty of human existence into stark relief like having children does, and few things feel more emblematic of that dichotomy than watching a toddler dance to an 80s pop song about the fleeting thrill of a one-night stand while trying not to fall on his diaper-cushioned butt. 

Pen Pal – “All the Lights” & “Here With You”

Before he passed, Bret and I, along with my wife, Sarah, made an album together. This was during the pandemic, and the way we recorded it is that Sarah and I would send tracks back and forth with Bret from our respective lockdowns. The project became a lifeline during those bleak months. As a musician, I’m a hobbyist at best, and I was lucky to make music with this much more talented and accomplished duo. These are the last two songs on the record, and my favorites. “All the Lights” is a composition of Bret’s to which I added lyrics—it’s about returning to New York after being gone. “Here With You”  is a love song I wrote for Sarah, and that she sings beautifully, a song about reaching a point in life when staying home to eat pad thai and watch Top Chef with the person you love is more enjoyable than partying. If Scott learns anything in Fail Sons, he learns this.   

Silver Jews – “The Wild Kindness”

A few years ago, I got the lyrics “shine out in the wild kindness” tattooed on my thigh in memory of Bret, who was a huge Silver Jews fan. I gave Scott, in Fail Sons, the same tattoo. David Berman’s lyrics can be elliptical, and I’m not totally sure what he means by the line. But I like the idea of a wild kindness; I imagine that, like wild blueberries, it is more fibrous and intense than the cultivated kind.

Paul Simon – “St. Judy’s Comet” & “Rene and Georgette Magritte With Their Dog After the War”

When my second son couldn’t sleep at night, I’d sing two songs to him in his crib: The Grateful Dead’s “Ripple” and Paul Simon’s “St. Judy’s Comet,” which, itself, is a song about singing to a child at bedtime: “If I can’t sing my boy to sleep, well it makes your famous daddy look so dumb.” Fail Sons is, in part, about becoming a father, and the challenge of adjusting to that new life role. I learned this song from my old roommate, Jordan, who used to play and sing a gorgeous cover of it when we lived together in Austin in our early twenties. This summer, Jordan and I went to see Paul Simon play at Forrest Hills Stadium in Queens, where Simon grew up—a full circle moment for both him and us. Simon did not play “St Judy’s Comet”, but he played another favorite deep cut from Hearts and Bones, “Rene and Georgette Magritte With Their Dog After the War,” a crushingly beautiful song about the painter and his wife dancing naked in a hotel room to 1950s doo-wop. Another full circle moment: Jordan told me that he now sings “St. Judy’s Comet” at bedtime to his own young son.

Island Boy – “Ashes”

I met Jordan and another friend, Jes, during my junior year abroad in Australia. They both went to Columbia, and I’m not sure I would have ended up in New York if I hadn’t visited them there the following year and fallen in love with the city. On that visit I met Richard Hunter Rivera, who was Jes’s boyfriend at the time, and is now her husband. In 2014, he released a reverb-soaked Caribbean dream pop record called Basic Instincts under the moniker Island Boy that I’ve had in heavy rotation for more than a decade—Richard even performed songs from it at my wedding. There’s something very calming to me about his music, and I like to listen to it when I’m overstimulated, which was pretty much all the time while I was trying to write Fail Sons in a New York apartment as two energetic boys bounced off the furniture. I recommend playing it after one gin and tonic and half of a 5mg THC gummy, which is my ideal combination of substances these days.

Yo La Tengo – “Everyday”

I never used to write to music, but while working on Fail Sons I made an effort to wake before sunrise and work for a bit before my kids got up. I wasn’t always successful at getting myself to do this, but on the days that I did, I always put on Yo La Tengo’s And Then Nothing Turned Itself Inside-Out to set the mood. To me this album is the sound of pre-dawn, a specific shade of darkness that I wanted to capture. It’s the sound of two guys in a car on an empty highway in the dead of night.

Rilo Kiley – “A Better Son/Daughter”  

This is the other song that makes me cry, though by the end of it I’m screaming at the top of my lungs, ready to take on the world. It’s the song I listen to when I’m low, the song I reach for to feel less alone. It is a song about depression, and also about fighting your way out of depression, and I can’t think of another piece of art that so deeply resonates with my own experience of these subjects. Sarah and I saw the Rilo Kiley reunion tour when they came through New York last summer, and the catharsis of screaming along to this song with an entire crowd of aging Millennials was unparalleled.  


also at Largehearted Boy:

Adam Wilson’s playlist for his novel Sensation Machines

Adam Wilson’s playlist for his short story collection What’s Important Is Feeling


For book & music links, themed playlists, a wrap-up of Largehearted Boy feature posts, and more, check out Largehearted Boy’s weekly newsletter.


Adam Wilson is the author of four books: the novel SENSATION MACHINES (Soho 2020), the novel FLATSCREEN (Harper Perennial 2012) the collection of short stories WHAT’S IMPORTANT IS FEELING (Harper Perennial 2014), and the novel FAIL SONS (Soho 2026).


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