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Prologue

Host Ira Glass, with a recording of a 1962 Frank Sinatra, Dean Martin, and Sammy Davis Jr., appearance at the Villa Venice, a club outside Chicago. What's fascinating about Sinatra is how he is so many different people at once, and they're all on display in this recording: sentimental crooner, cruel woman-baiter, bully, goofball.

Act Three: History Lesson

Ira and music contributor John Conners on Sinatra's worst songs. And a brief history of what makes that 1950s Sinatra sound so great, with Will Friedwald, author of the definitive book on Sinatra's music, Sinatra! The Song Is You: A Singer's Art.