Studs Terkel was a pivotal figure in the popularization of oral history as a literary genre and he is a key point of reference in today’s cultural radio and podcasting worlds. He was also one of the central synthesizers and champions of Chicago literature, drawing deep inspiration from earlier writers and advocating for subsequent generations. This chapter explores how Terkel crafted a variety of inventive “literary lives”: 1) Urban Literary Mythmaker, 2) Eclectic Disc Jockey, 3) Coach for Chicago’s Literary Scene, 4) Co-founder of a Peoples’ Oral History, 5) Soapbox Poet, 6) Global Literary Ambassador, 7) Sidewalk Professor, 8) Memory Palace Archivist, and 9) Humanist Trickster. Key biographic events in Terkel’s life and his links with other key Chicago writers are explored.