In 1939, earning up to $60,000 a week in Depression-era money, Artie Shaw stopped playing in the middle of a live radio broadcast at the Cafe Rouge in New York, walked off the bandstand, and fled to Mexico. This episode explores the psychology of Arthur Jacob Arshawsky, a deeply introverted kid raised in New Haven who faced anti-Semitism, saved grocery-store wages to buy his first saxophone, left home at 16 to tour, and built one of the biggest empires in American music only to repeatedly dismantle it.

The discussion covers his 1935 piece Interlude in B-flat, which paired a clarinet and rhythm section with a classical string quartet years before the term third stream existed, the 1938 explosion of Begin the Beguine, his choice of the brooding Nightmare as a theme song, and his decision to hire Billie Holiday and tour the segregated South. I ...