The songs that make up Dare Dukes’ new album, Prettiest Transmitter of All, are a striking combination of incisive intelligence and sweet, doleful hooks. Looking past the shiny surfaces of American life, the Savannah, GA-based singer-songwriter chronicles the everyday world, mining the margins for the eccentric characters and bizarre events that are the heart of his music.

Born and raised in the exurb of San Jose, California, Dare grew up as the state blossomed into what he calls, "exit-ramp...