On a freezing Chicago morning in the late 1960s, a man in a transit uniform climbed into the driver’s seat of a city bus while, thousands of miles away, a young David Bowie was recording one of his songs. William “Billy Boy” Arnold wrote “I Wish You Would” and “I Ain’t Got You,” played the driving harmonica on Bo Diddley’s “I’m a Man,” and helped lay the sonic blueprint of electric blues and rock and roll, then spent years driving a bus and working as an Illinois parole officer. In this deep dive we trace a life that maps the gap between cultural influence and economic reality for Black blues artists in the mid-20th century.

We begin in a South Side household of 16 children around 1935, where a harmonica was the one instrument a kid could afford and carry into a private sonic world, and follow the teenage Arnold to informal lessons from John Lee “Sonny Boy” Williamson I shortly before Williamson’s death in a street robbery. From his 1952 debut “Hello Stranger” on the Cool label, which gave him his nickname, we move to the March 2, 1955 Checker Records session where he overdrove a cupped bullet microphone through a tube amp behind Bo Diddley, and to the original solo track he cut that same day that the label shelved for 37 years.

• How the “churn and burn” singles labels of the 1950s treated sidemen as disposable and buried original work
• Why Arnold’s Vee-Jay recordings reached British teenagers through merchant sailors known as the Cunard Yanks, and how the Yardbirds, David Bowie and Sweet transformed them
• The case for viewing his day jobs as dignity and survival rather than tragedy, with a steady paycheck, health insurance and a pension
• His European renaissance on the 1975 American Blues Legends tour, a 1977 John Peel session for BBC Radio 1, and 1979 London recordings with the Groundhogs
• Late-career albums for Alligator Records like “Back Where I Belong” and “Eldorado Cadillac,” a 2014 Blues Music Award nomination, and a 2021 memoir from the University of Chicago Press