Podcast: Frank Sinatra - The Legend and Reality. 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.

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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. Show Highlights. Why Frank Sinatra was both the most popular and most despised man in the military during WWII (0.

Why music in America got really terrible after the war (0. How Frank Sinatra went from being one of the biggest stars in America to not being recognized in Times Square (0. How Frank Sinatra revolutionized American music, created the pop standard, and catapulted himself to legendary status (1. The music arranger that helped Frank create some of his biggest hits (1. How Sinatra was different from other crooners of his era (1. The source of Sinatra’s personal demons and the problems they caused in his life (2. Why Sinatra was drawn to the mob (2.

The time Frank Sinatra started a fight with John Wayne while dressed up like a Native American woman (2. Why Sinatra was so power hungry and how it ruined his life (3. What drew Sinatra and JFK together (3. Sinatra, Kennedy, and the mob (4. How the Rat Pack got its start at the Sands Hotel (4. Why Sinatra will always be an enduring icon of masculinity (5.

And much more! Resources/People Mentioned in Podcast. Kaplan’s first volume on Sinatra — Sinatra: The Voice. Goodbye, Darkness by William Manchester.

Westbrook Pegler, the Hearst columnist that went after Sinatra for his links to the mob. Ava Gardner, Sinatra’s second wife and on- again, off again lover. Nelson Riddle, the music arranger responsible for many of Sinatra’s hits. Dolly Sinatra, Frank’s mother. Sam Giacana, Chicago mob boss. Judy Campbell, mistress of both JFK and Giacana.

Sinatra introduced her to both men. From Here to Eternity (Sinatra won a Best Supporting Oscar for it)The Rat Pack. Sammy Davis, Jr. James Kaplan’s Essential Frank Sinatra List.

James was kind enough to put together his list of essential Sinatra albums along with the best song from each. If you’ve never listened to Sinatra, start off with these. Sinatra: The Chairman is an engaging and nuanced look at a fascinating and complicated man. Besides learning about the life of Sinatra, you’ll get a good dose of mid- century American pop- culture history as well.

Listen to the Podcast! 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 we like to tell ourselves. In reality, Frank Sinatra’s life, very, very complex.

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Today on the podcast, I talk to James Kaplan about his concluding volume of his definitive biography on Frank Sinatra. It’s entitled Sinatra, the Chairman, and on the show, James and I discuss how Frank 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 how that connected JFK and the Mob together, and we talked about Frank’s enduring appeal as an icon of American masculinity.

A great show. When you’re done, be sure to check out the show notes for this podcast at AOM. IS/Sinatra. You’ll find links to people and stories mentioned in this episode, as well as a suggested Frank Sinatra playlist from James Kaplan, Frank Sinatra’s biography. James Kaplan, welcome to the show. James Kaplan: Delighted to be here, Brett.

Thanks so much for having me. Brett Mc. Kay: Your second biography, your biography of Frank Sinatra came out last year. It’s called the Chairman, the subtitle, and it picks up right after Frank Sinatra won the Academy Award for best supporting actor for From Here to Eternity. You talk about in the book that before he won this award, Sinatra’s career was pretty much in the tank.

I’m curious, can you give us a little back story? How did Frank Sinatra, going from making thousands of bobby soxers faint during World War II, to people couldn’t even recognize him on the streets in New York City?

James Kaplan: Yeah. Well, the book that just came out was the second volume of my biography of Sinatra, second and final. The first volume was called Frank, the Voice, and covered his rise to incredible superstardom, mainly during World War II.

World War II was really what jet propelled Frank Sinatra’s career to its apex during those years, because, in that time, he was singing these ballads of yearning that so rhymed with the way the country was feeling, feelings of gentle sadness and missing the boys who were away fighting overseas. Of course, Frank was not away fighting overseas. He had been classified 4- F. A lot of people suspected that, and called him a draft dodger. William Manchester, who wrote a great history of the Armed Forces in the South Pacific in World War II, where he, also, served very bravely as a Marine, said that Sinatra was the most despised man in the Armed Forces, because all the guys fighting overseas felt that Sinatra, the draft dodger, was back at home fooling around with their women, and, in many cases, they were right. He wasn’t a draft dodger.

He really did have a punctured ear drum, but the perception lingered. Despite the perception though, he sold a ton of records in World War II. After the war, very, very quickly things changed in America. The political climate became very conservative, and the popular culture of America really became extremely conservative after World War II, and tastes in popular music shifted gears just like that overnight.

Suddenly, people were no longer interested in the ballads of yearning. Suddenly, the Big Band era, which had begun ten years previously in about 1. America was in this odd state of jubilation and fear. Jubilation because the war was over, and fear because of the rise of the Soviet Union.

That accounts for the political conservatism, and, also, I think the popular culture, too. Popular music really got pretty terrible in the wake of World War II very quickly. There are all kinds of novelty songs. People wanted escape after World War II, so they were listening to stuff like How Much is that Doggie in the Window, and Sinatra, who was still recording for Columbia at that point, but, unlike every other popular singer, had enough power to dictate what he could record.

Still, he decided to go along with the tide. He did record a number of these crummy novelty numbers, Tennessee Newsboy, most infamously the worst record he ever made, Mama Will Bark. His career, after World War II, went down the tubes for a few reasons.

It wasn’t just that tastes in popular music had changed. It was really a multi- determined problem, and a lot of the problems Frank created for himself. He was, in 1. 94. Havana, Cuba to attend a Mafia Summit Conference. Officially he went because he was there to entertain all these top mobsters. It’s, also, been alleged over the years, that he brought a suitcase packed with cash for Lucky Luciano, as tribute, and he was sighted in Havana by a columnist for the Hearst papers, and this columnist began to write disparaging columns about Sinatra’s affection for the Mob. The Hearst papers were very politically conservative.

Again, chiming with the times. Frank was a dyed in the wool liberal Democrat. He was an FDR Democrat. The Hearst papers hated him for that, and, suddenly, they had something to call him out for. That wasn’t enough for Frank. He, also, from the day he set foot in Hollywood, he began stepping out on his young wife, Nancy, with all kinds of Hollywood starlets, and in 1.

He was sighted with Lana Turner, and then he began this famous affair with Ava Gardner, and in 1. That wasn’t all. His record label, Columbia, dropped him, because he wasn’t selling records. His movie studio, MGM, dropped him for various reasons, but they had gotten tired of him at that point. His agents dropped him.

He wasn’t selling records. He wasn’t really making movies.

He married Ava in 1. Frank and Ava, she began to get sick of his moping around, and so his marriage wasn’t even working well then. It was a perfect storm of events, and, again, Frank himself had a lot to do with almost all of them.

Brett Mc. Kay: He’s at the bottom of his career, the lowest of lows. From what you’ve read and researched about him, did he purposely think, “I got to do something about this. I got to do something to kick start my career.” I mean did he deliberately start thinking about how he could catapult himself back into .

The most important thing to Frank Sinatra throughout his entire working life, from the time he first started singing professionally in his very early twenties, then went on the road with Harry James and then Tommy Dorsey, then went out on his own as a singer, through his decline, into his comeback, and until the very end of his singing career . Every minute of every day, Frank Sinatra was thinking about his singing and about his career. That was his priority, and so you can bet that during those years of decline, he was obsessing every waking minute about how he could come back. Chat Dating Free Personals 20. Easier said than done though.

Easier thought about than done. He was incredibly frustrated, incredibly depressed.