In his roles as both Frank Sinatra’s road manager and friend, Tony Oppedisano enjoyed unrivaled access to the man many consider America’s greatest 20th-century entertainer. The two met in 1974 at the New York City club Jilly’s when Oppedisano was 21 and Sinatra 56. Little did the author of “Sinatra and Me: In the Wee Small Hours” know that he had not just met his vocalist hero but someone he would spend many nights and early mornings with until Sinatra’s death in 1998.
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With so much already having been written about the Chairman of the Board, Oppedisano wisely avoids trying to compose a little-needed second-hand chronological biography. Instead, he briefly recounts his own experiences growing up and then gaining Sinatra’s respect and confidence. The heart of the book then contains thematic chapters of reminiscences Sinatra shared about his loves, family, artistry, political and charitable work and supposed mafia ties. Finally, Oppedisano recounts the singer’s passing and the machinations needed to keep the paparazzi from being invasive and various family members from openly squabbling.
So, is “Sinatra and Me” a juicy tell-all? Hardly. While Oppedisano shares an insider’s perspective, he does so largely in service of maintaining Sinatra’s positive image. While not glossing over Sinatra’s legendary temper, nor his demanding nature and fickle romantic heart, Oppedisano largely wants readers to see the best of his subject. The rumors about Sinatra’s ties to the mob? Untrue and unfounded. His devotion to his children and family? Absolute. His hush-hush monetary and personal support of friends and charitable causes? Outrageously generous.
So, is “Sinatra and Me” a mere puff piece? Also, no. Having the author recount reminiscences shared with him by Sinatra might seem like a recipe for bland retellings, but Oppedisano, aided by writer Mary Jane Ross, shares the tales with punch and panache. Readers get the benefit of Sinatra having shared these stories after considering them over decades. Late-in-life wisdom seeps through as Sinatra recounts regrets about leaving his first marriage, takes stock of who his true friends are and tries to keep his music career flourishing as executives and producers quietly imply or insist he is washed up. Tales of feuds between Sinatra, his last wife, Barbara, his first wife, Nancy, and his children, rather than tawdry, come off as compellingly tragic.
Perhaps the most surprisingly interesting portion of the book may be Oppedisano sharing his own life story and details of first entering Sinatra’s orbit. Despite their age difference, the two men found much to bond over, from their proud Italian heritage to their close families to their musicianship, Oppedisano having worked his way up the New York City club scene in his teens and early 20s as a singer and jazz musician. Oppedisano discovers an ability to direct, inspire and comfort people that leads to a career producing projects, managing artists, and acting as Sinatra’s sounding board, confidant and protector. That ultimately ends in the difficult work of discretely trying to control the chaos swirling around Sinatra’s death, the writer’s own grief having to be put aside for weeks as he wades through the practical work of such terrible times.
In his “Source Notes,” the author expresses his frustration that Sinatra himself became resigned to the idea of writers sharing their own versions of his life, no matter how far off base. Oppedisano remembers saying to his friend and boss, “‘But Frank, the truth is the truth.’” Sinatra’s response? “‘If you feel that passionately about it, then you fix it.’” “Sinatra and Me” may not set the record straight about every misconception of its title subject but not for lack of Oppedisano trying. That the results of such a quest prove so readable, human and sympathetic testifies to the writer’s powerful memory and singular life experiences.
John Young teaches seventh-grade language arts and plays in the rock band The Optimists.
First Published: June 17, 2021, 10:00 a.m.
Updated: June 17, 2021, 10:28 a.m.
