JOHN K. SAMSON That calculator watch makes even flannel look cutting edge.

THERE'S A SONG titled "The Last And" on John K. Samson's new solo album Provincial that is, at least tangentially, about The Simpsons. Specifically, the song was unwittingly inspired by the torrid and complex relationship between Edna Krabappel and Principal Seymour Skinner. "It's kind of a beautiful and sad subplot in The Simpsons canon," Samson says.

The Winnipeg-based frontman for the Weakerthans is a hyper-literary songwriter whose affinity for his songs' characters is palpable, from the lovelorn teacher and her boss to the lonesome grad student investigating an abandoned sanatorium on the edge of the continent. Samson's songs are universally personal—excavations of the brilliant and tragic moments in all our lives. "I think fiction is an incredibly important political tool. I love George Saunders. I'm paraphrasing, but he said, 'Fiction encourages people to feel empathy for other people, and if you can do that, it makes it much harder to kill them.'"

Provincial marks the first time Samson, long obsessed with the cultural and geographic minutia of his homeland, has so plainly explored the physical space of Manitoba. Song by song, the album travels on dusty back roads, searching for some connective hint of meaning. "It's certainly something I grapple with," says Samson, "what home is. And that attempt to make connections with other people—really, the most important thing we do in our lives is try to build community and empathize and connect with other human beings."

Connection through song comes easy for Samson, but it wasn't always so in life. "I've had encounters with depression and mental illness, and it's certainly a theme that keeps coming up in my life," he says. Perhaps it's what lends such tenderness to Samson's narratives; intimate familiarity with darkness often unavoidably births light. The people and places on Provincial are painted lovingly, images we know even if we don't. Like the fictional Springfield, Samson's Manitoba seems to exist everywhere and nowhere, the setting of our shared history. "I still know so little about [Manitoba]," Samson explains. "The communities we live in are so mysterious and interesting, actually. I guess I learned that I still have something to say about these places."