Simon Cropp doesn’t just write songs — he crafts worlds out of the ordinary. On his debut album Paperback Dream, the 28-year-old songwriter invites listeners into his universe of small-town stories, worn highways and quiet revelations. With a voice both gentle and resolute, Cropp illuminates the beauty and heartbreak tucked inside daily life.
Raised between Lanesboro, Minnesota and Decorah, Iowa — two communities known for their vibrant arts scenes — Cropp’s musical roots run deep. His parents worked in the arts, and public school music programs let him experiment with nearly every instrument.
“The first band I joined in high school was called the Bread and Butter Stringband,” he recalled. “I was immediately obsessed with playing in bands — tinkering with PA systems, hustling for gigs, dreaming about booking a tour.”
That early curiosity evolved into a way of life. Cropp now spends more than 200 days a year on the road, performing solo, with Slapdash Bluegrass, and as a side musician on pedal steel — a recent obsession. His van doubles as both a tour bus and home.
“It’s good for my sleep to be in a consistent environment each night,” he told me with a laugh.
Cropp’s songwriting has drawn comparisons to his biggest inspiration, John Prine, which he considers both “lofty” and deeply meaningful: “I’m really into writers who can set everyday stories to melodies that are easy to sing along to.” Like Prine, he balances humor and heartbreak, crafting songs that feel lived-in and generous.
That sensibility shines in “Mrs. Jansson and Mr. Kaplan,” a small-town love story between “a Mennonite mama and a hippy-dippy dad.” With the lyric, “Saturday mornings at the old farm stand, selling all the fruits of their labor and the land, keeping every secret of the love they had,” Cropp captures the humor and tenderness of everyday romance — a snapshot of the Midwest that feels as familiar as a neighbor’s wave on a dirt road.
Among the album’s standouts is “Turkey River Turnaround,” rooted in the community that’s become one of Cropp’s musical home bases. The Turkey River valley near Elkader has nurtured a thriving network of musicians who’ve embraced his work.
“The song is a collection of stories about the river and the people who live on it,” Cropp explained. “My friend, songwriter Forrest McCurren, says that looking at a body of water is one of the best things a person can do to disrupt troubled thought patterns — and I wrote this song to remind myself of that.”
Paperback Dream was recorded over 10 months with producer Tim Evenson and collaborators including Vinnie Donatelle of The Last Revel. Others include Lauren Anderson and Adam East who feature on “Resignation Letter,” which confronts the tension between creative ambition and personal connection. With Anderson’s aching harmonies and East’s searing guitar, it’s a meditation on the sacrifices inherent in a musician’s life.
“I hope my songs encourage people to look for beauty in the mundane,” Cropp said. “I like to sing about things that people have in common — rivers, work, highways.”
Cropp’s sincerity is his signature. Whether performing in a small Iowa cabin or a packed Minneapolis club, he approaches his craft with humility and heart. “We tell ourselves stories in order to live,” he said, quoting Joan Didion. In Paperback Dream, Simon Cropp tells his stories with a clarity that invites us to live inside them, too.
This article was originally published in Little Village’s November 2025 issue.
