This episode was originally released on September 9, 2014. Listen to help prep for the next episode of our new season, The Old Man is Still Alive.

Humphrey Bogart is perhaps the most enduring icon of grown-up masculine cool to come out of Hollywood’s first century. But much of what we think of when we think of Bogart — the persona of the tough guy with the secret soft heart, his pairing on-screen and off with Lauren Bacall — coalesced late in Bogart’s life. Today we take a look at how Humphrey Bogart became Bogey, tracing his journey from blue blood beginnings through years of undistinguished work and outright failure (both in the movies and in love), to his emergence in the early 1940s as a symbol of wartime perseverance who could make sacrifice seem sexy. Finally, we’ll look at what it took to get him to take the leap into a fourth marriage that seemed to saved his life … until the world’s most glamorous stoic was faced with cancer.