Originally Published: 21 JUL 23 08:51 ET

Updated: 21 JUL 23 11:05 ET

By Catherine E. Shoichet, CNN

(CNN) — Legendary singer Tony Bennett, best known for singing “I Left My Heart in San Francisco,” has died, according to his longtime publicist, Sylvia Weiner.

He passed away Friday at age 96.

In a career spanning eight decades, Bennett wowed Bob Hope and Frank Sinatra, performed live on MTV, had a cartoon cameo on “The Simpsons” and recorded two albums of duets with Lady Gaga, winning 19 Grammy Awards and a lifetime achievement award from the Recording Academy along the way.

In 1965, Frank Sinatra told LIFE magazine Bennett was “the best singer in the business.”

Bennett and his family opened up in 2021 about the singer being diagnosed with Alzheimer’s disease in 2016, but the public had been unaware of his declining health because he kept on performing.

No matter how many awards he won, or how many grueling hours on tour he logged, or how many times he belted out his signature song, Bennett often said he’d never worked a day in his life – because he loved performing so much.

His stint as a singing waiter at a New York restaurant was only the beginning. Even then, at age 15, Bennett knew he’d found his calling.

“I just decided that … I would love to become successful, and if I didn’t, I’m going to do this the rest of my life,” he told CNN’s Larry King in 1998. “I loved it.”

He is survived by his wife, Susan Benedetto, his two sons, Danny and Dae Bennett, his daughters Johanna Bennett and Antonia Bennett and nine grandchildren.

How Anthony Benedetto became Tony Bennett

Anthony Dominick Benedetto was born on August 3, 1926, in Astoria, New York.

He sang his first nightclub gig in 1946, at the Shangri-La. His big break came three years later, when famed entertainer Bob Hope heard him performing in Greenwich Village.

It was Hope who suggested a simpler stage name for the budding star, Bennett told CNN in 2004.

“He took me from that show and put me right on the stage at the Paramount, and he said, ‘What’s your name?’ I said, ‘Anthony Dominick Benedetto.’ He said, ‘Well, that’s too long for the marquee. Let’s simplify it and call you Tony Bennett.’”

The next year the renamed Bennett signed with Columbia Records and began churning out a string of hits, including “Because of You” and “Rags to Riches.”

But it took another decade for Bennett to find his signature song.

His performance of “I Left My Heart in San Francisco” won Grammys for best record and best male vocal performance. But Bennett said he never imagined the song would take off. His music director had pulled it out of a drawer and brought it along on tour for a San Francisco show, hoping to win over the crowd in a place where Bennett had never performed before.

“I thought it was going to be a local song in that area,” Bennett told CNN. “I bet on the other side of the record. … We had no idea it was going to become my signature song. It made me a world citizen.”

The song became so popular, and so associated with Bennett, people would often ask if he ever got tired of singing it.

“I retort by saying to them… ‘Do you ever get tired of making love?’” Bennett said in a 1982 interview with NPR’s Terry Gross. “I happen to love the fact that it’s made me this popular. It’s allowed me to be as creative as I want in any…musical endeavor. … I’m very grateful for that song.”

In 2016, as Bennett celebrated his 90th birthday, the city of San Francisco unveiled a statue of him in front of the Fairmont Hotel, where he first performed the song in 1961.

His son helped him bounce back after a slump

But it wasn’t all smooth sailing for Bennett. Two of his marriages ended in divorce. And the singer battled drug and financial problems in the 1970s as rock music took over the airwaves and his popularity waned.

“I thought I was singing well. You know, you think you’re doing great, but you’re not,” Bennett told CNN in 1998. “It’s not as great as being sober. I’m higher than anybody right now by being sober because I’m wide awake. I’m completely honest.”

Eventually one of his sons, Danny Bennett, took over as his manager. And the singer’s career bounced back in the 1980s and 1990s as new audiences found his music.

He appeared on “The Simpsons” as a cartoon version of himself in 1990. And in 1994, he appeared on “MTV: Unplugged” with guest appearances by kd lang and Elvis Costello.

“Tony Bennett has not just bridged the generation gap, he has demolished it,” a New York Times review noted at the time. The album from that performance would later earn Bennett a Grammy.

In a 2004 interview with CNN’s Larry King, Bennett said he had managed to appeal to generations of fans by never changing his tune.

“Everything today is all demographic, you know. Everything is split up … I never did that,” Bennett said.

Instead, he said he modeled himself after “old masters” like Jack Benny, Charlie Chaplin and Walt Disney.

“They played to the whole family…and so, if they hit, everybody bought it,” he said.

Singing wasn’t his only love

Bennett was also an accomplished painter; some of his work is part of the Smithsonian’s permanent collection.

He began painting as a child and studied it at New York’s High School of Industrial Art.

Even as his singing career took off, Bennett made a point of sketching as often as he could and painting every day.

“It’s a very relaxing, wonderful thing, and it’s very difficult, but if you have a passion, you go for it, and it stays difficult,” Bennett told CNN’s Larry King in 2004. “No matter how good you become, you’re still not finished yet. You know that there’s so much more you have to learn.”

Bennett said that push to keep learning and growing – through music and art – kept him going. At times when others might be slowing down or thinking about retiring, Bennett boasted he was just getting started.

Sinatra called him ‘the best singer in the business’

Many great musicians counted themselves among Bennett’s biggest fans. The Kennedy Center in Washington proclaimed Bennett a “singer’s singer” when awarding him with its prestigious honor in 2005. Wishes for the singer’s 95th birthday in 2021 came in from the likes of Paul McCartney, Jon Bon Jovi and Bono.

“He excites me when I watch him – he moves me,” Sinatra said. “He’s the singer who gets across what the composer had in mind, and probably a little more. There’s a feeling in back of it.”

The admiration was mutual – not just between Bennett and Sinatra, but between Bennett and many other artists who he sought out as collaborators. In 1999, Bennett and his wife Susan Benedetto founded an arts high school in New York and named it for Sinatra.

And in the last decades of his career, Bennett became known for his duet performances. He released “Duets: An American Classic” in 2006 followed by “Duets II” in 2011.

Bennett told “Larry King Live” finding different voices that complement each other was the key to a successful duet.

“A classical album with Ella Fitzgerald and Louis Armstrong, you know, his wonderful rasp. That’s where mine came from, being influenced by him. And then there’s Ella, you know, singing so sweet and beautiful and that combination of contrasts – Bing Crosby, Louis Armstrong, those are the best duets,” Bennett said.

‘Things can change, and you can still be magnificent’

Recording “Duets II,” Bennett found a new musical partner in Lady Gaga. The duo sang “The Lady is a Tramp” for that album, then went on to collaborate on two albums together, “Cheek to Cheek” in 2014 and “Love for Sale” in 2021.

In August 2021, the duo sang side-by-side in a series of concerts at Radio City Music Hall. Months earlier, Bennett’s family had revealed he’d been diagnosed with Alzheimer’s and battling the disease for years. His wife told AARP magazine that sometimes Bennett didn’t understand where he was or what was happening around him. But whenever music started playing, she said, Bennett was back to being his old self.

That connection to the songs he’d sung for decades was on full display at the Radio City Music Hall performances.

“I think he really pushed through something to give the world the gift of knowing that things can change, and you can still be magnificent,” Lady Gaga told “60 Minutes” after the show.

Bennett used to point out even when he sang songs over and over, each performance was unique; certain phrases, he said, would come out differently every time.

And as he sang “Fly Me to the Moon” that night in August 2021, looking toward the rafters with his eyes gleaming, the words of the catchy love song seemed to take on an even deeper meaning.

“Let me sing forever more. You are all I long for, all I worship, and adore.”

The crowd roared, and Bennett beamed.

A few weeks later, his family announced those concerts would be his last.

A recording of the show became a CBS special, airing in November 2021, just weeks after Bennett set a world record for being the oldest person to release an album of new material.

In April 2022 he won his 19th Grammy, along with Lady Gaga, for “Love for Sale.”

Even at 95, even with Alzheimer’s, he was still learning, growing and singing his way into millions of fans’ hearts – in San Francisco and around the world.