A Tribute to Tony Bennett (1926-2023)

I've been a fan since childhood—and it feels like I've lost a part of my extended family

Tony Bennett (photo by Andy Witchger)

I was just listening to Tony Bennett’s music last night. I do that often. And then, this morning, I learned of Bennett’s death at age 96.

This was sad news for me, but not unexpected. Bennett had been diagnosed with Alzheimer's in 2016, and had stopped performing two years ago. His fans knew that this was coming, but that still didn’t lessen the blow.

I probably own 30 or 40 of his albums, and his singing has been part of my life since childhood—when my Sicilian father played Tony Bennett records at our family home. At times, it almost felt like Bennett was a member of my extended family.

And that wasn’t by chance. His singing possessed a rare intimacy and sense of direct communication. He wore his heart on his sleeve—I think this is what my gentle father responded to in Bennett’s music. I know that’s what grabbed me. You really did feel that he was singing just for you.

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Back in 2013, I got enlisted by CBS to write the liner notes for the recently rediscovered album of Tony Bennett’s 1962 performance with Dave Brubeck. I was very excited to do this—but I had to pass an audition to get the job.

I think somebody in the Brubeck family had recommended me, but the Tony Bennett camp didn’t know who I was. I had to convince them that I knew enough about Bennett’s life and times to deserve this assignment. A phone call was set up, and I would have to demonstrate my mastery of Bennett-ology.

Hah—I passed that test with flying colors. And for a good reason. I’d been preparing for it all my life.

He was a true gentleman, a person of absolute integrity and commitment to fairness in every sphere of life—as a soldier in World War II he helped liberate prisoners in a Jewish concentration camp, and he later marched in Selma with Dr. Martin Luther King.

I retained my childhood enthusiasm for Tony Bennett’s music even during those tough times after he lost his Columbia recording contract, and many people thought he was washed up—a figure from the past that was out-of-touch with contemporary trends in music.

Around that time, Woody Allen released Broadway Danny Rose—a film in which he plays a struggling agent who is reduced to representing failing musicians. Many believed that the pathetic singer Lou Canova, a key character in the movie, was a cruel parody of Tony Bennett.

That’s how low Bennett had sunk during this period.

I remember going to the Fairmont Hotel in San Francisco to hear Tony Bennett sing back then. Even at his lowest point, he was always a revered figure in that establishment—it was where he had first sung “I Left My Heart in San Francisco.” There’s now a statue of Bennett in front of the hotel.

Tony Bennett statue outside the Fairmont Hotel in San Francisco

That song not only became a hit, but also a symbol of the entire city. And, once again, listeners felt that personal connection. The song rose the charts shortly before the escalation of the Vietnam War, and many soldiers who shipped out of San Francisco to fight in Southeast Asia heard it as a story about them and their loved ones back home.

But when I saw Tony Bennett at the Fairmont that night, he hadn’t enjoyed a hit since “I Left My Heart in San Francisco” left the chart in 1962. I looked around at a roomful of senior citizens. As far as I could tell, I was the youngest person in attendance at the performance.

So nobody was more surprised than me when Tony Bennett gained a young audience after the success of his 1994 appearance on MTV Unplugged. He was almost 70 years old, and found himself back in the mainstream of American popular music.

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COMING TOMORROW ON THE HONEST BROKER: A GUIDE TO TONY BENNETT’S GREATEST JAZZ COLLABORATIONS

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But it was absolutely deserved.

He still sang those songs with total conviction—and the songs themselves are timeless. Many people laughed at the idea of going on MTV to sing tunes by George Gershwin, Irving Berlin, and Cole Porter. But Bennett knew exactly what he was doing. These were some of the greatest vocal compositions ever written, and he had absolute confidence in the music and his ability to deliver it to a new audience.

After that point, Bennett’s career never faltered. In fact, he became something of a legend in American music—one of the great comeback stories in 20th century entertainment. He sold ten million albums in his 80s alone.

But Bennett never rested on his laurels. He continued to sing at a very high level. When the music world threw a party for Bennett’s 90th birthday, he got on stage at the very end and sang brilliantly. Even a devoted fan like me was stunned. I had never heard a singer perform so well at such an advanced age. I don’t think I ever will.

As recently as February 2016, Bennett won a Grammy for his Jerome Kern tribute album, performed with pianist Bill Charlap. And this was no symbolic gesture or lifetime achievement award—Bennett (and Charlap) earned that statuette. This is a beautiful record, and you would never guess that the singer was 89 years old when it was released.

That’s an inspiration whether you’re old or young. But Bennett was a role model in so many other ways. He was a true gentleman, a person of absolute integrity and commitment to fairness in every sphere of life—as a soldier in World War II he helped liberate prisoners in a Jewish concentration camp, and he later marched in Selma with Dr. Martin Luther King.

Even in the final years of his life, Bennett was a generous mentor and promoter of others—and was constantly looking for ways to give young people a boost. You never heard him say a cruel or thoughtless word about anybody.

I could fill up an entire article just with stories of his acts of kindness. He radiated decency and generosity of heart. That showed up in his life and his music. I heard it in the songs, and you probably did too.

We have lost him, and even if the music lives on, his presence will be deeply missed. But we can still learn from him—and it’s a worthy lesson both onstage and off.

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Tomorrow I will share my favorite jazz collaborations from Tony Bennett’s discography.