Chesney Henry Baker Jr. had the looks of a Hollywood teen idol, a voice that melted hearts, and a trumpet instinct so natural that Charlie Parker chose him for West Coast gigs. A few years later he had his front teeth knocked out in a street fight, lived on welfare, and pumped gas in California. This episode explores that paradox, starting in Yale, Oklahoma, in 1929 with a father who abandoned a guitar career during the Depression, a move to California in 1940, a trombone too heavy for a young teen, and a trumpet mastered within two weeks. The army became his accidental university, exposing him to Dizzy Gillespie through V-Discs in postwar Berlin and later placing him near San Francisco’s bop clubs before his 1951 discharge.

The hosts cover the 1952 Gerry Mulligan Quartet and its counterpoint approach, the signature My Funny Valentine, beating Miles Davis in 1954 trumpet polls, the polarizing album Chet Baker Sings, William Claxton’s photographs, and the decision to turn down a Hollywood studio contract for life on the road. That road brought heroin, pawned instruments, Rikers Island, a 1955 European tour that continued after pianist Dick Twardzik died of an overdose, and his second wife Halema serving six months in an Italian prison for smuggling drugs for him. After the 1966 Sausalito beating destroyed his embouchure, he spent three years at a gas station before agonizingly relearning the horn with dentures, relocating to Europe, recording 11 albums in 1979 alone, demanding silent rooms, playing on Elvis Costello’s Shipbuilding in 1983, and starring in Bruce Weber’s documentary Let’s Get Lost before his fatal fall from an Amsterdam hotel window on May 13, 1988, at 58.

• Learning jazz entirely by ear, from radio tunes to V-Discs in Berlin
• Why Charlie Parker paired his own fiery bebop with Baker’s fragile restraint
• How the choice of the road over Hollywood opened the door to addiction
• What losing front teeth means for a trumpet player’s embouchure
• The European comeback, drumless ensembles, and a death ruled an accident