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Ol’ Blue Eyes, the Chairman of the Board, the Voice.

Frank Sinatra has been an icon of masculine coolness and swagger for decades. During his lifetime, he was able to create a myth and legend around himself that continues to exist today. But, like all legends, when you look closer at them, you discover that the reality is much more complex than the story.

Today on the podcast, I talk to James Kaplan about Sinatra’s complex life. Kaplan is the author of a definitive two-book biography of Sinatra and recently published the concluding volume: Sinatra: The Chairman. On the show, James and I discuss how Sinatra’s career went in the tank after World War II, and what he did to not only revitalize it, but catapult himself into legendary status. We also get into Frank’s foibles, his incessant drive for power, and his enduring appeal as an icon of American masculinity.

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