In American popular music, we often glorify rebellious artists and “outlaws.” But The Midnight Special reveals an untold story about the way criminal justice has impacted the lives and work of US musicians. Examining five pivotal albums, Colin Asher’s narrative traces the history of twentieth-century incarceration from southern prison-farms to the heroin-driven drug war that villainized a generation of jazz artists to the dawn of mass incarceration. He argues that white artists, unlike their Black colleagues, often avoided severe punishment or even profited from jailtime. And he shows how prisons occasionally incubated talent, but more often shortened careers and distorted the public’s perception of musicians and their value to society. With keen musical analysis and thrilling biographical portraits of Huddie Ledbetter, Elmo Hope, Johnny Cash, Ike White, and Tupac Shakur, The Midnight Special writes the history of prisons into American music—a story as important as it is overlooked.