REVIEW: Why Sinatra Matters by Pete Hamill

Though separated by several generations, I have always felt connected to Frank Sinatra through my Italian-American heritage. I still fondly recall dancing around my living room on top of my father’s feet to “Come Fly With Me,” and other Sinatra classics. My paternal grandfather—a proud Italian-American—was of the same generation as Sinatra, born just two months after him to Italian immigrants. And yet, despite the connections through familial traditions and histories, Sinatra had long been an abstract figure to me—a fragment of my heritage rather than a real person.

In his semi-biographical book Why Sinatra Matters, Pete Hamill brings form and depth to the musical icon, like a sculptor chiseling away at a block of marble. Hamill expertly dodges the trite nicknames and dispels the Godfather-esque myths, cutting through to the man as best we can know him. Over the course of six chapters Hamill explores Sinatra’s formative childhood, laborious rise to fame, grisly fall from favor, and epic comeback. He does not truly begin to dig into the character of the music until the final chapter, in which Hamill identifies the teamwork of Sinatra and arranger-composer Nelson Riddle as the key to the iconic Sinatra-sound. Hamill hits the nail on the head in his analysis of the music, particularly his notes on Riddle’s “light” treatment, use of flutes, and the breathing room he gives Sinatra’s voice. Riddle uses higher pitched instrumentation that doesn’t compete with Sinatra’s timbre, a quality which is expertly executed to the point of subtlety. But once you know to listen for it, you hear its variations in each of Sinatra’s records. Trilling flutes, soprano violins; the majority of the compositions occupy the upper register, giving Sinatra the space he needs to emote in the genuine way for which he is known.

Everything up until chapter six illustrates the personal, musical and cultural experiences and circumstances that paved the pathway to Sinatra’s signature sound. To do so, Hamill bounces deftly through time and space, interspersing biographical content and interviews with Sinatra and associates with recollections of his own personal interactions with the artist. The anecdote he uses at the beginning of the text is particularly effective at illustrating what Hamill claims is one of Sinatra’s defining characteristics: loneliness. Hamill recalls sitting with Sinatra and other notables in a New York saloon, debating everything from sports to literature into the early morning hours. Sinatra comes off as distant, barely tolerating the sound of his own voice coming through the jukebox before finally walking out alone into the twilight. Perhaps more essential to his character than loneliness, however, is his identity as the son of Italian immigrants, an identity which Hamill views through Sinatra’s childhood experiences as well as historical events.

This book is, in many ways, a history of 20th century America viewed through the lens of Sinatra’s life. Many of America’s most defining issues of that era were equally as significant to the development of Sinatra’s career, and ultimately his lasting cultural importance. As Hamill follows Sinatra’s life parallel to issues of immigrant prejudice and racism, Prohibition, the Depression, and the many wars of the 20th century, he delves into the titular question: why Sinatra matters. He was a hero to Italian-Americans and immigrants of all nationalities. He “perfected the role of the Tender Tough Guy.” But most far-reaching is Sinatra’s ability to emote the imperfections of the human condition. As Hamill puts it, “his work will endure as long as men and women can hear, and ponder, and feel. In the end, that’s all that truly matters.”


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