Tony Bennett appreciation: Decade after decade, he left his heart in every fan’s memories

A great singer passes, and we fall back into his work to honor the loss.

Not long after hearing of Tony Bennett’s death, I revisited the 1975 album Bennett recorded with the peerless jazz pianist Bill Evans. I was driving on the Kennedy Expressway, going about 7 miles per hour. Minus the freeway construction, this is how millions of us first encounter, and then return to, our favorite singers and musicians who last and last. At home, doing things, not doing things. Or in the car, going wherever we’re going.

Listening to that album again Friday, hearing Bennett’s singularly operatic delivery crack open the heartache in the Leonard Bernstein/Betty Comden/Adolph Green “On the Town” standard “Some Other Time,” and then activate the powerful yearning of “Young and Foolish” — well. It’s something. Especially on the day of Bennett’s passing, two weeks before his 97th birthday.

The man born Anthony Benedetto, whose family came from Calabria, Italy, was something too. He had a huge, generous heart. He marched with Martin Luther King Jr. and Harry Belafonte. He was alert and awake to his times, and to his country.

Chicago loved the guy, though it was hardly unique in that regard. From 1984, a few years before he regained worldwide stardom, to 2019, Bennett graced 32 separate seasons at Ravinia Festival, performing outdoors for the satisfaction of thousands and thousands of fans.

“Total class. Gracious gentleman. What you saw onstage is what you saw backstage,” Ravinia senior artistic producer Erik Soderstrom said Friday.

Before the Ravinia era, Bennett played Chicago, for decades, at the Edgewater Beach Hotel’s Beach Walk, or Chez Paree in Streeterville.

“A show stopper who sings the audience out of its chairs and has to beg his way off the floor after a crowded hour of high voltage vocalizing.” That’s how William Leonard reviewed Bennett in the Tribune in 1957. By then the singer had scored a few hits, earlier in the ’50s, with “Because of You” and “Boulevard of Broken Dreams” and “Rags to Riches.”

Howard Reich listened to and interviewed Bennett many times, as Tribune arts critic and jazz chronicler from 1983 to 2021, plus some freelance Tribune years before that. In 1975 Reich was a senior at Northwestern University majoring in piano performance; for independent study course approval, he reviewed Bennett at Orchestra Hall. Bennett was on a bill with Lena Horne. The review, though unpublished, “launched my whole career as a critic,” he said.

And it got him thinking about why Bennett was not like any other popular or jazz vocalist.

For one thing, he told me, “Bennett was the only major white singer who didn’t fall under the spell of Frank Sinatra. Bobby Darin, Vic Damone, Steve Lawrence, Harry Connick Jr. — they all work within the Sinatra template. Bennett comes from a completely different vantage point. He’s basically a romantic operatic singer who happens to be doing jazz. He doesn’t have Sinatra’s beautiful, lustrous instrument; Bennett’s sound is leathery, craggy, pugnacious.”

He’s “the non-Sinatra,” Reich said.

Bennett’s longtime association with the Columbia Records label went kaput in 1971, around the time singer reluctantly agreed to record some “new,” “now” material that didn’t really suit him. The decade was not an easy one. Still, Bennett toured, valiantly, capping his gigs with the 1962 audience favorite “I Left My Heart in San Francisco.”

In the late 1980s, something wonderful happened: Bennett came back, under son Danny’s management and with a little help from MTV. It didn’t happen because of a change in artistic direction; he was still doing the glorious, time-tested stuff he cherished, by Cole Porter, Irving Berlin, Jerome Kern, newer cats such as Michel Legrand, so many other greats. And there he was, first gradually, then suddenly: cool again.

There’s a 1994 “MTV Unplugged” concert, viewable on YouTube, in which Bennett floats through the brilliant Kurt Weill/Ogden Nash song “Speak Low.” Most of the audience, very likely, is hearing it for the first time, and the way Bennett swings it, gently, intimately, it’s like a love potion poured by one generation’s musical exemplar into another generation’s ears.

Bennett toured all the way into his 90s. He and his family went public with his Alzheimer’s disease diagnosis in 2021. Music, said his third wife, Susan Benedetto, kept him as present in his life as humanly possible.

In 1991, early in the glorious resurgence of Bennett’s career, I spent part of a weekend with him in San Francisco for a story. We ate dinner at his friend Gino’s place on Columbus Street. Bennett sketched a little picture of me while we had our espresso. We played tennis the next morning, by which time I thought to myself: If you have to work on a weekend, there is no better way to do it. He beat me in two sets, exactly the way he sang: powerfully but effortlessly. How do you do it? I asked him. You’re 65 and you’re playing like you’re 30, and I’m 30 and playing like I’m 130. What’s your secret?

“Cream sauce,” Bennett said. “I avoid it.”

During dinner the night before, I asked him why the music he loved apparently had come back in favor, and why he thought careers like his had their ups, downs and, if you’re lucky, ups again.

He smiled. “It’s a young country, only a couple hundred years old,” he said. “Other societies are thousands of years old, and they’re smarter; they know what’s good about America. We don’t always know. We’ve always had this silly streak, I guess. ’Cause we’re young and foolish, y’know?” Like the song.

Jazz, he told me, “is the thing that’s ours. It’s the thing we invented. It was America’s first real expression of: Just keep going. Keep improvising. Make up the moment.”

May each new generation discover anew the music Tony Bennett championed, like no one else.

Michael Phillips is a Tribune critic.

mjphillips@chicagotribune.com

Twitter @phillipstribune