The man who would tell Ingrid Bergman, "Here's Looking at You, Kid," at the conclusion of Casablanca (1942) was born Humphrey DeForest Bogart in 1899. He would become one of the twentieth century's greatest icons of tough masculinity, a complex blend of "good guy" and "bad guy" at a time when World War II had many Americans re-examining their personal codes of loyalty, honor, and character. Underneath his coarse exterior, Bogart, or simply "Bogie," betrayed an underdog vulnerability and a genuine desire to find the "right" answer in a world that was increasingly chaotic and off-kilter. The star was also well known for his celebrated marriage to co-star Lauren Bacall, whose sultry wit reflected his cynicism but who always drew out his romantic, heroic side.

Although Bogart became known for playing brutish characters from the wrong side of town, he was raised in the world of...