Tony Bennett, a Legend in the Worlds of Jazz and Pop Music, Dies at 96
He was the only guy I ever knew who was equally close to both Ella Fitzgerald and Judy Garland, both personally and musically, and who had absorbed the key strengths of both of them.

In 2021, the family of Tony Bennett announced that the legendary singer was suffering from Alzheimer’s disease, and that his final performance would be on his 95th birthday, August 3 of that year. I had already started putting together my annual Tony Bennett birthday radio show when the news came in this morning that he had passed away.
Let’s begin during the last days of the old WNEW — back when that AM radio station was the standard-bearer of what we had even then started to call “The Great American Songbook,” by which we meant the music of the Gershwins, Rodgers & Hart, and Irving Berlin as sung by Sinatra, Ella Fitzgerald, and company. Tony Bennett was having one of his many big birthdays — possibly his 65th — and WNEW was doing a special Bennett tribute and invited me to speak. I agreed, of course, and was interviewed by one of the station leaders, the late Stan Martin. It so happened that about two days later, I had lunch with Tony Bennett’s son and manager, the ever-resourceful Danny Bennett.
What surprised me about those two meetings was that Stan asked me the same question that Danny and I asked each other, and that the answer was exactly the same in both cases. The question was: What makes Tony Bennett so great?
Independently of one another, we both came to the same conclusion: The main thing that makes Tony so wonderful, and why his career lasted so long, was that he was somehow both a jazz singer and a pop singer at the same time. Ella Fitzgerald was a great jazz singer who occasionally made pop-oriented records; Frank Sinatra was the greatest of all popular singers, and also frequently made a purely jazz album; Nat King Cole was both, but usually at different points in his career.
Tony Bennett was somehow a jazz artist and a pop star at the same time — the only figure in American music who was always both.
On one hand he celebrated the legacy of Louis Armstrong, and of such collaborators as Duke Ellington and Count Basie, but also Charlie Parker and Miles Davis. On the other hand, he was a great avatar of old-school show business, Jimmy Durante, Sophie Tucker, and the singer who was his very earliest influence, Al Jolson.
He was the only guy I ever knew who was equally close to both Ella Fitzgerald and Judy Garland, both personally and musically, and who had absorbed the key strengths of both of them. He was also the only artist to fully fathom and assimilate the greatness of Louis Armstrong and Jimmy Durante — not to mention Louis Prima.
At the end of his long career, the younger generation thought of him as an old-style crooner — and, it goes without saying that it was due to his remarkable talent and longevity that they were thinking of him at all when virtually all his peers were either gone or just forgotten. Yet Tony didn’t have the slick, high-polished pipes of most of the swinging lovers who came along in the wake of Sinatra. If anything, he was a traditional crooner only in the earliest, most operatic phase of his career, but even then he was trying to move in a jazz direction and add a swinging dimension to his work.
From the 1960s onward, Tony had cultivated a voice that owed as much to Armstrong and Durante as it did to Sinatra and Bing Crosby. In 2016, on the occasion of Tony’s 90th, I had the opportunity to speak with his old friend and collaborator, the composer and orchestrator Johnny Mandel, who had known Tony since the ’40s.
He told me, “He’s the only singer that doesn’t sound like Frank, and never tried to. I’ll tell you why: He comes from a totally different place, and the closest I can think to it is Louis Armstrong. He doesn’t sound like Louis, but he reads a song like Pops did. Tony is a jazz musician at heart. And if you listen to the way he phrases, it’s quite a bit like Louis. That’s the reason he doesn’t ever sound like Frank. He just comes from somewhere else. He doesn’t sound like anyone.”
Tony Bennett was perpetually learning and growing; his irascible sideman of many years, trumpeter Ruby Braff, admired how Tony never stopped trying to learn something new, even at an age when most of his contemporaries were content to rest on past achievements.
Tony openly didn’t approve of the new pop music that started coming in when he was only about 30; but his objections were more toward the mentality of planned obsolescence that became a business model for pop in the late ’50s. Still, he appreciated talent, which is why he didn’t hesitate when he had the opportunity to work with Amy Winehouse on his 2011 album “Duets II” and then his more extensive collaboration with Lady Gaga.
If you asked Tony to name his favorite song, he never hesitated; it was always, “I Left My Heart in San Francisco.” He loudly trumpeted that he never got tired of singing it every night, even as he did for nearly 60 years. “That’s the song that made me a citizen of the world,” he said.
Then there was his side career as a visual artist, a specialist in both oil paintings and watercolors, landscapes and portraits; he usually exhibited under his birth name, Anthony Benedetto. “They consider me a singer who also paints,” I heard him say more than once. “Which is funny, because I only sing three or four nights a week, but I paint every single day.”
In 2011, when Tony turned 85, Sony released a package called “Tony Bennett: The Complete Collection.” It wasn’t, even though it included 73 CDs and three DVDs — there were still at least another five or six CDs worth of material omitted; some enterprising collectors filled those in. Then, he went and recorded another 10 or so albums worth of new material anyhow. He would release new music even into his 90s.
More than one commentator has said that it’s impossible to imagine the world without him, but Tony Bennett will always be with us, and we are all the beneficiaries of his amazing legacy.