There are musical storytellers—and then there’s the low-key but wildly ambitious Paul Simon, who copyrighted his first song with partner Art Garfunkel when they were in their early teens. Born in Newark, New Jersey, in 1941, Simon mixed the mass appeal of ’50s rock ’n’ roll with the introspection of the singer/songwriter era, opening up a universe of emotional terrain previously unexplored in popular music. (Just listen to the playful poetry of 1968’s “Mrs. Robinson” or the existential ache of “The Sound of Silence”—songs you could whistle along to, or subject to rigorous literary analysis.) Though he was originally associated with folk, Simon is a remarkably eclectic artist, drawing variously on gospel and jazz, Brazilian batucada, and, perhaps most famously, South African township music. His landmark 1986 album, Graceland, helped build a bridge for his collaborators Ladysmith Black Mambazo, Hugh Masekela, and Miriam Makeba during the height of apartheid. For as uplifting as his music can be (think: the chorus chant of “Cecilia,” the rocksteady of “Mother and Child Reunion,” and the bright horns of “You Can Call Me Al”), at its heart is a profound bittersweetness. Embarking on his farewell tour in 2018, Simon celebrates an inimitable career spent mining themes of aging, separation, and loss with a muted reserve, suggesting that all things—good and bad—do pass.