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    #186: The Legend and Reality of Frank Sinatra

    enMarch 25, 2016

    Podcast Summary

    • Frank Sinatra's career decline and revivalDespite draft status during WW2, Sinatra's ballads resonated. Post-war shift towards conservatism led to decline. Novelty records failed to revive career. Academy Award win revitalized career, leading to legendary status.

      Frank Sinatra's career faced a significant downturn after World War II due to changing political and cultural climates. Despite his draft status during the war, Sinatra's ballads of longing resonated with the nation. However, post-war America shifted towards conservatism, and popular music tastes changed, leading to a decline in the popularity of Sinatra's style. Sinatra tried to adapt by recording novelty numbers, but these records did not revive his career. It was only after winning an Academy Award for Best Supporting Actor that Sinatra was able to revitalize his career and ultimately achieve legendary status. The complexities of Sinatra's life, including his foibles and relentless pursuit of power, further contributed to his enduring appeal as an icon of American masculinity.

    • Frank Sinatra's rock bottom momentsDespite personal scandals and career setbacks, Frank Sinatra's determination and obsession with his craft led him to revolutionize popular music in the 1950s.

      Frank Sinatra's career hit rock bottom after World War II due to a combination of external factors and personal choices. He attended a mafia summit in Havana, bringing a suitcase of cash for Lucky Luciano, which led to negative publicity. Simultaneously, he began publicly dating numerous Hollywood starlets, including Lana Turner and Ava Gardner, which led to his wife leaving him. These events, coupled with his declining record sales and movie offers, left Sinatra at the lowest point in his career. Despite his depression and frustration, Sinatra remained determined to revive his career. He had always prioritized his singing and career above all else, and this obsession drove him to make a comeback. During the 1950s, a time of transition in music, Sinatra didn't just tap into the changing tastes; he revolutionized popular music with his unique style, bridging the gap between the big band era and the emergence of rock and roll.

    • Frank Sinatra's signing to Capitol Records and partnership with Nelson RiddleFrank Sinatra's collaboration with Alan Livingston and Nelson Riddle revolutionized popular music by introducing the concept of the standard, timeless songs that continue to be cherished today.

      Frank Sinatra's signing to Capitol Records in 1953, against the backdrop of the rise of rock and roll, was a pivotal moment in music history. Dropped by Columbia Records, Sinatra was a struggling artist until young executive Alan Livingston recognized his talent and teamed him with arranger Nelson Riddle. Together, they revolutionized popular music by introducing the concept of the standard – timeless songs that continue to be recorded and cherished today. Sinatra's transformative influence extended beyond his ability to feel the pulse of America; he actively shaped it through his collaborative recording process, making him a true musical visionary.

    • Frank Sinatra's Complex Relationship with His MotherFrank Sinatra's mother's volatile personality influenced his uncertain relationships, but his meticulous production of music made him an enduring icon

      Frank Sinatra was not only a musical genius, but also a complex character with paradoxical personality traits. He had an uncanny ability to make himself dislikable despite his immense talent. One significant influence on his complex personality was his mother, Dolly Sinatra, who was a volatile and impatient woman. Sinatra's relationship with his mother left him uncertain of her love and conditioned his relationships for the rest of his life, particularly with women. He was a deeply feeling man who struggled to attain intimate relationships. Sinatra's musical genius was evident in his meticulous production of his recordings, where he knew exactly how he wanted each song to sound. He worked closely with brilliant arrangers, but ultimately, he was the boss. Despite his conflicts and complexities, Sinatra's music continues to captivate audiences, making him an enduring icon in music history.

    • Sinatra's Complex Past and Musical GeniusGrew up in a tough environment, idolized powerful men, volatile temper, fearless, inner demons, alcohol, shaped legendary music career

      Frank Sinatra was a complex man with a troubled past, innate sensitivity, and extraordinary musical talent. He grew up in a tough environment where being a musical genius made him an outsider. His inability to form intimate relationships, combined with his highly strung nature, led him to idolize the powerful and strong men around him, often the Italian-American mobsters. Sinatra's volatile temper and fearlessness, even when facing much larger men, were fueled by his inner demons and a propensity for alcohol. Despite his challenges, Sinatra's unique blend of strength, sensitivity, and genius shaped his legendary music career.

    • Frank Sinatra's relentless pursuit of powerSinatra's insecurities, experiences, and desire for control fueled his pursuit of power, leading to incredible success but ultimately leaving him disconnected and seeking solace in alcohol and partying.

      Frank Sinatra's pursuit of power was a defining characteristic of his life. From his early years feeling weak and powerless, to becoming a superstar and losing it all, Sinatra understood the importance of power in both his personal and professional life. He used his power to regain his status and success, but ultimately found that it left him unable to connect with others and led him to seek solace in alcohol and partying. Sinatra's obsession with power stemmed from his insecurities as an Italian-American and his experiences with his mother, as well as his desire to be the best and have control over his career. Despite the negative consequences, Sinatra's relentless pursuit of power was a driving force behind his incredible success and enduring legacy.

    • Power and Influence brought Sinatra and Kennedy togetherTwo iconic figures, Sinatra and Kennedy, were drawn to each other by their mutual desire for power and influence, with Sinatra admiring the mob and Kennedy's allure of Hollywood and beautiful women.

      Frank Sinatra and John F. Kennedy were drawn to each other due to their mutual desire for power and influence. Sinatra admired the mob's power and Kennedy was captivated by Hollywood's glamour and the allure of beautiful women. Their relationship was complicated, with Kennedy's double standards and Sinatra's longing to be part of the mob or Kennedy's inner circle. Despite their differences, they found common ground in their pursuit of power and influence. It's important to remember that both men were complex figures with flaws and virtues, and their legacies continue to be debated and celebrated in American history.

    • JFK's relationship with Sinatra strained by mob tiesJFK's association with a mobster's girlfriend led to a public humiliation for Sinatra, ending his political alliance with the Kennedy family. Sinatra shifted to supporting Republicans as a result.

      The relationship between President John F. Kennedy and Frank Sinatra was complicated by Kennedy's association with a mobster's girlfriend, leading to a public humiliation for Sinatra and the end of his political alliance with the Kennedy family. This incident occurred during Kennedy's presidency, when he was discovered to be sleeping with a woman who was also involved with the Chicago mob boss, Sam Giancana. J. Edgar Hoover, the FBI director, informed Kennedy's brother and attorney general, Robert Kennedy, who then instructed Kennedy to sever ties with Sinatra. The humiliation deeply affected Sinatra, and he shifted his political allegiance from the Democrats to the Republicans, supporting Ronald Reagan in his gubernatorial campaign. This episode marked the beginning of the end of Sinatra's political life as a liberal Democrat. The Rat Pack, a group of entertainers closely associated with Sinatra, also played a role in this period of his life.

    • The Rat Pack's accidental formation and disrupted movie shootThe Rat Pack, a legendary group of entertainers, formed during a movie shoot where they disrupted each other's acts, creating off-color humor and impromptu performances that delighted crowds. Their image of stylish, handsome men acting silly on stage continues to appeal.

      The Rat Pack, a legendary group of entertainers including Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop, formed almost accidentally during a time when Vegas was known for its naughtiness and breaking rules was acceptable. They initially disrupted each other's acts during a movie shoot for "Oceans 11," and the crowds loved their off-color humor and impromptu performances. The Rat Pack's image and style have endured, despite the fact that much of their material is now considered offensive. Quincy Jones, an African American musician and arranger who worked with Sinatra, recalled that Sinatra made racial jokes during his shows at the Sands in the late 1960s. The Rat Pack's influence continues to be felt, and their image of stylish, handsome men acting silly on stage is still appealing to audiences.

    • Frank Sinatra's iconic status: More than just aura and Rat PackFrank Sinatra's unique ability to convey raw emotions through singing voice made him relatable and desirable, advocating for tolerance and acceptance of vulnerability in men.

      Frank Sinatra's enduring iconic status as a symbol of American masculinity can be attributed to more than just his aura and the mystique of the Rat Pack. His unique ability to convey raw emotions through his singing voice, which exuded both masculinity and vulnerability, made him relatable and desirable to both men and women. Despite his politically incorrect jokes and falling outs with friends, Sinatra's advocacy for tolerance and acceptance of vulnerability in men set him apart and continues to resonate with audiences today. His voice, filled with an acceptable vulnerability, is a testament to Sinatra's genius and a timeless reminder that it's okay for men to express their feelings.

    • Insights on Sinatra's Music and LegacyKaplan discusses Sinatra's innovative approach to music, his influence on the entertainment industry, and his enduring legacy. Check out Kaplan's books for more information and a suggested playlist at aom.is/Sinatra.

      Kaplan, the author of the book "Sinatra: The Chairman," shared insights from his research and personal connection to Sinatra's music. The conversation touched on Sinatra's innovative approach to music, his influence on the entertainment industry, and his enduring legacy. If you're interested in learning more about Sinatra and his music, Kaplan encourages readers to check out his books, available on Amazon and his website, James Kaplan.net. For a suggested playlist and additional resources, visit aom.is/Sinatra. As a reminder, if you enjoy the Art of Manliness Podcast, please consider sharing it with others and leaving a review on iTunes or Stitcher. Stay manly!

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