In 1951, Bennett's first big hit, "Because of You," reached No. 1 on the pop charts and sold more than 1 million copies. And because of Bennett, music lovers of all ages would fall in love with the classic standards of the pre-rock and roll era that he interpreted — and reinterpreted — throughout his career.
"He didn't bridge the generation gap, he destroyed it," his son and manager, Danny Bennett, said.
Danny Bennett told "CBS Sunday Morning" on Friday that his father, who had lost much of his memory to Alzheimer's, stayed connected to the songs he cherished until the very end.
"I'll share something typical with Alzheimer's. The person will go in and out, and he would have times when he was alert, and other times when he wasn't, and he was with Susan, his wonderful wife, and he said, 'Susan, was I always popular?' And she said, 'Yeah, of course you were.' He said, 'Good, because I stayed with quality.'"
The son of Italian immigrants, Anthony Dominick Benedetto was born in a working-class neighborhood of Queens, New York, where he began singing at an early age.
"To this day, I remember very clearly saying to myself: If I never make it, I don't care. I'm just gonna keep singing. You know, I'd love to make a living singing," Tony Bennett said in a 1992 interview.
He served in the U.S. Army during World War II, seeing combat in France and Germany.
"I think he suffered post traumatic stress syndrome like a lot of veterans did and didn't talk about at the time," his son Danny Bennett said. "All he said was, 'War is the worst, lowest common-denominator in humanity,' and he came out a pacifist."
After the war, the singer, then known as Joe Bari, opened for Bob Hope, who asked what Bennett's real name was.
"And I said Anthony Dominick Benedetto," Tony Bennett recalled in a 2014 interview. "'Well, that's a little long, but why don't we call you Tony Bennett?' Bob Hope gave me my name."
Bennett wasn't an immediate hit. "The first review I got said that, well, another Italian mama's boy with… with a gravel voice has come about. That was the first review. It was a terrible review, I was shocked by it."
In 1962, Bennett recorded what would become his signature song, "I Left My Heart in San Francisco."
"He told me that he really had barely seen a cable car," NPR host Scott Simon, who co-wrote Bennett's memoir "Just Getting Started," said.
"At the time he saw the sheet music, he was on a 1961 nightclub tour. He was in Hot Springs, Arkansas. And Tony began to sing, and said the bartender, who was cleaning up, said, 'Damn, if you guys record that. I'll buy your first copy.'" The song won him the first of 20 Grammys.
Bennett also gave his voice to the civil rights movement. In 1965, he joined the march from Selma to Montgomery, Alabama. Privately he was equally committed to the cause.
Some of Bennett's biggest fans were his fellow artists. Frank Sinatra once told Life Magazine, "For my money, Tony Bennett is the best singer in the business."
"He changed my career," Bennett told Anthony Mason. "All of his fans wanted to find out about what he was talkin' about."
Danny Bennett said his father drew inspiration from instrumentals.
"Tony's line was: Listen, if you copy one person, you're a thief. If you're copying many, he says, you're doing research," Danny said. "I mean, the secret: Tony emulated saxophone players. It was instrumental. That's where he got his inspiration, through the musicians."
"I think Tony took songs that a lot of people knew, and he put such personality into them, he put such a depth of feeling," Simon said. "He had a great voice, but he also had a kind of, you know, rasp in it that was almost like you could… you could hear somebody making the station announcements on the number 7 train."
In the 1970s, Bennett's life went off the rails. Trying gamely but unsuccessfully to sing rock and roll, he was abusing alcohol and cocaine, at one point almost drowning in his bathtub.
"And I think something that was harder for him to talk about, but he touched on it with me was that it got bad because it affected his family and the relationship with his family, which I think is what really got to him, but, you know, he pulled himself out," Simon said.
He called on Danny, who took over his career. They decided that the songs of Bennett's past would be his way forward. By the early 1990s, he was in heavy rotation with groups like Pearl Jam and Nirvana.
"This is what he taught us: Music has a transcendent quality," Danny Bennett said. "Any great art has a transcendent quality. And when you are true to the art, that's why the masterpieces are hanging in the museums, right? There's no gimmick to Renoir."
A fitting comparison: When Bennett wasn't holding a mic, he was handling a brush. Bennett said he loved to paint as much as he loved to sing.
His own comeback may have explained his connection with the late British singer-songwriter Amy Winehouse.
"He knew her well enough to understand something of her troubles," Simon said. "He saw a future for Amy Winehouse and he wanted to put a reassuring hand on her and let her know that if she'd let her talents speak up, he would be there to support her."
They recorded duet "Body and Soul" just two weeks before Winehouse's death from alcohol poisoning at age 27.
Bennett found even greater success with Lady Gaga, who was in her own kind of artistic rut when the two met.
"He said, don't you ever, ever, ever, ever —again or in the future — let anybody take down the quality or the intelligence of what you do," Lady Gaga recalled.
Bennett took his final bow alongside Lady Gaga at Radio City Music Hall in August 2021.
Five years after his Alzheimer's diagnosis, the performance was a smashing success. But the disease had already taken its toll, as "60 Minutes" correspondent Anderson Cooper observed. Days after his performance, he had no memory of playing Radio City Music Hall.
But Danny Bennett said his father never forgot those songs.
"He was singing up until a week ago. You know, towards the end here, he became, you know, pretty much immobile. Put him next to a piano, and he turned to Susan, his wife, and he was just standing at the piano, and he said, 'What do you want to hear?' And she said, 'Whatever you want to sing.' And his last song, he sang 'Because of You.'"
"Which was his first big hit," Danny Bennett noted.
Danny Bennett said he was with his dad hours before he passed. "I roused him. He opened his eyes and he looked at me, with that smile, and said, 'Thank you.' And those were the last words he said to me."