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As a small boy, dreaming of becoming a professional singer, Anthony Dominick Benedetto sat by the radio in his family’s home in Astoria, Queens, New York, each week and listened to Major Bowes Amateur Hour. The winning group one night in 1935 was the Hoboken Four, and young Tony never forgot its 19-year-old spokesman, Frankie Sinatra. Tony studied Sinatra’s vocal technique, emulated his breathing and eventually became not only Sinatra’s closest friend but the entertainer Sinatra himself would call “the best singer in the business. He gets across what the composer had in mind, and probably a little more.”
Tony Bennett, who died Friday at age 96, according to his publicist, Sylvia Weiner, was best known for the 1962 hit “I Left My Heart in San Francisco,” which ranks 23rd on the Recording Industry Association of America’s list of the most historically significant songs of the 20th century. He first sang it in the Venetian Room of the Fairmont Hotel in San Francisco in 1961. Nearly 60 years later, during the COVID-19 pandemic, he led a citywide sing-along of the song in that same city to boost morale, tweeting everyone to “Spread the love and strength throughout the bay!”
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Bennett’s long style-setting career as a performer of traditional pop standards, big band music, show tunes and jazz rivals only Sinatra’s for ownership of the American songbook, with fans arguing for years about which singer had the better phrasing and timing or delivered the most emotional impact.
Unlike most singers of his generation, Bennett was able to not only resurrect his career after it flagged in the 1970s (and drug and financial problems took hold), but also to remake himself into a contemporary figure while holding on to the essence of his style. He achieved that in the 1990s largely through duets with younger performers such as k.d. lang and Elvis Costello, who crossed over to Bennett’s jazzy oeuvre instead of the other way around.
In 2014, pairing with Lady Gaga, he became the oldest performer to have a number 1 album, Cheek to Cheek. In his ninth decade alone, he sold more than 10 million recordings and celebrated his 90th birthday with a book of his reminiscences of important friends and influences (Just Getting Started), as well as a prime-time television special, Tony Bennett Celebrates 90: The Best Is Yet to Come.
“Tony’s all about moving forward,” his manager-son Danny said at the time. “He tells me, ‘Hey, as long as my voice doesn’t wobble and people like me, I’m going to keep singing until I die.’”
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