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. It follows him from Pearl Harbor and a Navy band in Guadalcanal to psychoanalysis, a cynical 1952 autobiography, elite marksmanship, eight marriages including Lana Turner and Ava Gardner, an appearance before the House Un-American Activities Committee in 1953, and the day in 1954 when he put down the clarinet for good.

• Why Shaw viewed commercial fame as a form of psychological torture rather than success
• The logistics and toxicity of touring the Jim Crow South with Billie Holiday in 1938
• How the Gramercy Five put a harpsichord inside a jazz band
• The collateral damage his abrupt band breakups and controlling behavior inflicted on musicians and partners
• Why the physical strain of a perfectionist’s embouchure led him to quit performing for the last 50 years of his life