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Famed Musician Tony Bennett Dies at 96

‘I Left My Heart in San Francisco’ singer’s career spanned 7 decades and multiple genres


Taylor Hill/FilmMagic

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.’”​

Even when he enjoyed sold-out tours, Bennett worked to improve his craft. “I still insist that I can get better as I go along,” he told The New York Times in 2016, adding that he had started studying the basics of jazz piano. “It’s the same way with painting,” he said. “I paint every day. And just by doing it every day, you get better.”​

Bennett paintings were exhibited in galleries around the globe, and several of his pieces are in the permanent collections of the Smithsonian American Art Museum in Washington and the National Arts Club in New York City. He published two books of his artwork, Tony Bennett: What My Heart Has Seen (1996) and Tony Bennett in the Studio: A Life of Art & Music (2007).​

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“Actually, in high school, there was a time that I was thinking about just concentrating on painting,” he said on the 2007 PBS American Masters biography of him, The Music Never Ends. “I asked my music teacher, Mr. Sondberg, for advice, and he encouraged me to stick with the music as well. So all my life, I have been singing and painting.”​

The son of an Italian immigrant who died when Bennett was 9, he rose from poverty, performing for money from age 13 and then working as a singing waiter in Italian restaurants. In World War II, he saw so much fighting and suffering in France and Germany that he later became a pacifist, evolving into that rare entertainer who mixed artistry and activism without alienating a segment of his audience.

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Tony Bennett performs on stage as local radio disc jockey Bill Randall (left) applauds and teenage girls scream in the audience at a high school in Cleveland, Ohio, in 1952.
Hulton Archive/Getty Images

In 1965, two years after winning the first of his 18 Grammys (for record of the year and also best solo vocal performance by a male for “I Left My Heart in San Francisco”), he walked with Martin Luther King Jr. in the march for voting rights from Selma to Montgomery, Alabama.​

He got his break in 1949, opening for Pearl Bailey in Greenwich Village. The entertainer Bob Hope was in the audience, invited him on the road and suggested he simplify his last name. The following year, Mitch Miller signed Bennett to Columbia Records and produced his first hit, “Because of You,” which soared to number 1 and stayed on the charts for 10 weeks, selling more than a million copies. His other hits of the era included “Cold, Cold Heart” (a pop rendition of the Hank Williams country song), “Blue Velvet,” “Rags to Riches” and “Stranger in Paradise.”​

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Bennett relied on the bel canto singing discipline and studied improvisation with the idea of adapting the human voice to the sounds of musical instruments.

He was married three times and had four children, including the singer Antonia Bennett. Along with his widow, Susan Crow Benedetto — a former teacher 40 years his junior who was president of the Bay Area Tony Bennett Fan Club when they first met in person — he founded Exploring the Arts, a charitable organization dedicated to supporting arts education, as well as the Frank Sinatra School of the Arts High School in Queens, New York.​

VIDEO: Tony Bennett Keeps Singing With Alzheimer’s

​In February 2021, Bennett’s family shared with AARP that the singer had been diagnosed with Alzheimer’s in 2016. Still, he continued to rehearse his music twice a week.​

 ​Pre-diagnosis Bennett was often asked about retirement. The question mystified him: “If you are creative, you get busier as you get older,” he once told The New York Times, pointing out that Pablo Picasso, Jack Benny and Fred Astaire worked “right up to the day they died.” ​

“I think if you have a passion for what you do, then there are no limitations on how long or how much you can accomplish,” he said. “When people ask me if I plan to retire, I say, ‘Retire to what? I am doing what I love best right now!’”​

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