Jackson plays the piano at a friend’s Miami home

Jesse Jackson is seated on the edge of a catamaran anchored out in Biscayne Bay, the nocturnal silhouette of an island visible in the distance. “In Miami, nature’s everywhere, but somehow here… there’s a kind of solitude that is really inviting,” he says. “It offers me an opportunity to quell things, and filter my experiences.” Nature is just one of the themes in Jackson’s songwriting. Though he may seem an anomaly in a Miami music scene largely dominated by electronica, he’s developed a devoted fan base that relates to his existential sense of melancholy and thoughtful lyricism.

Jackson’s early life was peripatetic. Born on the northwestern coast of Tuscany, he first moved from Italy—where his late father, the esteemed American artist Harry Jackson, had relocated—to Wyoming, to Maine, and then to Boston, where he studied saxophone at Berklee College of Music. “That’s where I got into theory, and the whole nuts and bolts of music,” he says. The sax gave way to guitar and banjo, as he gleaned inspiration from such greats as Leonard Cohen, Tom Waits, and Bob Dylan, melding jazz, blues, folk, and country inclinations into his own unique sound.

In 2000—after an underwhelming stint in Las Vegas—Jackson arrived in Miami, busking amid the mall-ish spectacle of Lincoln Road, a transplanted folk bard who chose to learn from the city: “I don’t relate to the clubbing scene, and when I first started performing here on the street, the disparity between the clubgoers and the homeless population used to make me really upset. [But] there’s a certain glitz about Miami that compelled me to dig, the way a journalist would dig for facts, and those facts are found in people, conversations, what’s around me, and in myself.”

For more than a decade, Jackson has played regular gigs both with and without a band at venues throughout the city, from far-gone haunts like Amendment XXI to the stalwart Churchill’s. But it’s only now, at age 34, that he’s releasing his first official album, an eponymous collection of original songs produced by Grammy winner Carlos Alvarez. It’s a beautiful, haunting record, with mood-enhancing tracks like the slow burn of “Leather” or the jazz-cool of “Go Away,” marked by low, subtle breaths of bass clarinet and liquid-like vibraphone tones, drawn from “the earth and the ether,” as he likes to put it.

“If you do the right thing, nobody’s going to care about the time it took,” he says. “It’s subjective for everyone, and things should take as long as they need to grow. But let’s just let the work stand on its own.”

Like what you're reading? Get it delivered straight to your inbox. Sign up now for our newsletters >>