Bill Callahan’s career has taken him from a misspent youth as a misanthropic lo-fi troubadour to maturity as a chronicler of American myths. He has sung in riddles, trafficked in obscure symbols, and eventually pulled back the curtain on his life as a husband and father. What connects the varied phases of Callahan’s career are his wry sense of humor, deep-seated empathy, and keen perspective on the human condition. Born in Silver Spring, Maryland, in 1966, Callahan got his start writing surly vignettes on his 4-track in 1988, under the alias Smog. Gradually, influenced by producers like Jim O’Rourke and John Congleton, his music became more intricate and open-hearted, with touches of folk and country adorning his elegantly economical storytelling. Eventually, leaning further into the iconography of the American West, he settled down in Austin and began writing under his own name, turning out a succession of richly textured, emotionally insightful albums like 2009’s Sometimes I Wish We Were an Eagle, 2011’s Apocalypse, and 2019’s Shepherd in a Sheepskin Vest, his tender yet unsparing tribute to family, from birth to death.