Bennett died in his hometown of New York, his publicist Sylvia Weiner said. In February 2021, he revealed that he had been diagnosed with Alzheimer’s disease five years earlier, but he soldiered on, in the recording studio and on tour, rarely performing a song the same way twice.

He and Lady Gaga headlined two shows at New York’s Radio City Music Hall in August 2021, after which he announced he was canceling his fall tour

His Facebook page noted Friday, July 21, that Bennett was “still singing the other day at his piano, and his last song was ‘Because of You.’” That was his first No. 1 hit.

The recipient of 20 Grammy Awards, including a Lifetime Achievement honor presented in 2001, he earned his final trophy in April 2022 for his work with Gaga on the album Love for Sale, his second acclaimed collaboration with her, becoming the second-oldest winner in history.

He sold about million records and charted albums in every decade from the 1950s to the 2020s.

Bennett’s initial superstardom came with the longing ballad “I Left My Heart in San Francisco,” which he first recorded in early 1962 after his arranger and pianist Ralph Sharon brought the song to him after Tennessee Ernie Ford passed on it.

Written by George Cory and Douglass Cross, two Bay Area transplants who had relocated to New York, “I Left My Heart in San Francisco” was placed on the B-side of “Once Upon a Time” by Columbia Records.

However, the tune about the city where “little cable cars climb halfway to the stars” made it to No. 19 on the Billboard Hot 100, then captured Grammys for Record of the Year and best solo vocal performance, male.

“I had hits before that song, and certainly a lot of hits afterward,” Bennett told San Francisco Weekly in 2016 interview. “But I never had a hit like that one. That song gave me international recognition.”

Bennett, though, would hit a rough patch, and amid personal crises that included tax problems and drug abuse in the late 1970s, he turned to his oldest child, Danny Bennett, to manage and resuscitate his career.

Bennett began targeting the younger crowd — showing up on the MTV Music Awards with the Red Hot Chili Peppers and  programs like The Simpsons and Late Night With David Letterman — while introducing them, without compromise, to the Great American Songbook.

He scored a hit with the 1992 album Perfectly Frank, homage to his idol, Frank Sinatra, then cemented his comeback with the 1994 release of MTV Unplugged, culled from a concert appearance on the music network.

Bennett perfected the art of the duet, teaming with Lady Gaga, Amy Winehouse, k.d. lang, Diana Krall, Christina Aguilera and Norah Jones.

Duets II, released on his 85th birthday in 2011, became the first No. 1 album of his career, and 2014’s Cheek to Cheek, his first LP with Gaga, made him, at 88, the oldest performer to have No. 1 album. He sold some 10 million recordings in his ninth decade alone.

He never thought about quitting. “As George Burns said, ‘Retire to what?’ You should do what you really like to do, love to do, and then just keep going forward,” he said in 2007. “The more you keep learning, the more life becomes important, and it makes you live longer.”

“One of the early gifts I got was from my mother,” he told Robert Sullivan for the 2007 book Tony Bennett in the Studio: A Life of Art and Music. “She always insisted on top quality. She would make those penny dresses, and the more she made, the more money she would earn. But even still, she’d throw away a bad dress. Always quality. Ever since, I never wanted to do a song that would insult the audience. That’s the way to make music that lasts. Like a dress that lasts.”

Just before he turned 10, he stood alongside New York mayor Fiorello La Guardia at the 1936 opening of the Triborough Bridge and sang “Marching Along Together.” It wasn’t long before his dad died, sending the Benedettos to live in an apartment building in Astoria, Queens.

He attended P.S. 141 and the School of Industrial Art, where he studied music and painted in Central Park for his homework assignments, but he had to drop out at age 16 to help support the family as a singing waiter. (He was inspired by his brother, Giovanni, who was nicknamed “The Little Caruso” after he performed solos as a teenager at the Metropolitan Opera.)

Benedetto was drafted into the U.S. Army in 1944, serving in the infantry on the front lines in France and Germany and helping to liberate a concentration camp. He remained in Europe after World War II to sing with a Special Services band until his discharge in 1946.

Back in New York, he studied singing on the G.I. Bill at the American Theatre Wing, took acting lessons and worked as an elevator operator while performing in nightclubs under the stage name Joe Bari.

Bob Hope saw him open for Pearl Bailey in Greenwich Village in 1949 (the only white kid i  show) and invited him to be his opening act at the famed Paramount Theatre in Times Square.

“Just before I’m going on, Hope tells me the name’s no good. Joe Bari’s no good. He asks what my real name is. I say Anthony Benedetto. That doesn’t do it for him either,” he said. “So he goes out and says to the audience, ‘And here’s a new singer, Tony Bennett!’ He had to introduce me twice because I didn’t know who he was talking about.”

Bennett was signed by Mitch Miller at Columbia and reached No. 1 in September 1951 with “Because of You,” followed by another chart-topper, a cover of Hank Williams’ “Cold, Cold Heart.” Those were the first of his 24 songs to make it into the Top 40.

In 1953, Bennett’s “Rags to Riches” also made it to No. 1, and “Stranger in Paradise,” from the Broadway musical Kismet, reached No. 2. But with rock ‘n’ roll getting popular, he shifted his focus to jazz with such albums as 1957’s The Beat of My Heart and LPs recorded with the Count Basie Orchestra.

In March 1965, he marched with Martin Luther King Jr. in Selma, Alabama, to support civil rights.

A month later, Sinatra was quoted in Life magazine: “For my money, Tony Bennett is the best singer in the world. He excites me when I watch him, he moves me. 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.”

A grateful Bennett said years later: “Sinatra’s fans became interested in me, and I sold out all over the world. He did change my career. I owe him so much.”

Amid the British Invasion, Bennett turned to easy listening versions of such songs as “For Once in My Life,” “MacArthur Park” and “Something.” After splitting with Columbia and recording for Verve Records, he launched his own label, Improv, in 1975, and made two albums with jazz pianist Bill Evans. However, Improv lasted just a couple of years and ended in bankruptcy.

In the ’70s with no recording contract, Bennett spent time performing in Las Vegas as his marriage to his second wife, Sandra Grant, was falling apart.

His first wife, Patricia, whom he had wed in St. Patrick’s Cathedral in 1952, had sued him for divorce on the grounds of adultery, and they split in 1971. He also was being hounded by the IRS for $2 million in back taxes and struggling with drug addiction, nearly dying of cocaine overdose in 1979.

“I was in a completely self-destructive tailspin,” he said, but he quit drugs, without going to rehab.

For his intimate MTV Unplugged concert, Bennett was accompanied by Sharon, Doug Richeson on bass and Clayton Cameron on drums and joined on songs by lang and Costello. When it was over, he glowingly told the audience, “This has been one of the most wonderful nights of my career.”

Duets: An American Classic, featuring collaborations with Paul McCartney, Elton John, Streisand, Bono and others, won three Grammys in 2006/A Rob Marshall-directed NBC special inspired by the album netted the singer the second of his two career Emmy Awards.

Duets II and 2013’s Viva Duets (collaborations with Latin artists like Gloria Estefan and Marc Anthony) followed.

As actor, Bennett appeared on ABC’s 77 Sunset Strip in 1963 and as Hymie Kelly, the friend of a self-absorbed movie star (Stephen Boyd), in The Oscar (1966). He was much better served playing himself, which he did in Muppets Most Wanted (2014) and on series including The Doris Day Show, Entourage and Blue Bloods.

Bennett also had a second career as an accomplished painter; he signed his works — three of which, including “Central Park,” are in the Smithsonian — using his birth name.

He married his third wife, former New York schoolteacher Susan Crow, nearly 40 years his junior, in 2007. They met backstage at one of his concerts when she was 19 and president of a San Francisco Tony Bennett fan club; they were together for 20 years before they wed.

In 2001, the couple founded the Frank Sinatra School of Arts in Queens. Eight years later, the school moved into a new $78 million home across from the Kaufman Astoria Studios.

Bennett was named a Kennedy Center honoree in 2005 and received the Gershwin Prize for Popular Song from the Library of Congress in 2017. (The latter represented a nice full-circle moment: One of the first songs he ever recorded — in 1949, when he was still going by Joe Bari — was George and Ira Gershwin’s “Fascinating Rhythm.”)

In addition to his wife and son Danny, survivors include another son, Dae; daughters Joanna and Antonia; and nine grandchildren.

He continued: “It is easy to believe that when this planet of ours gives forth its last ding-dong, Tony Bennett will be onstage in some worthy cabaret, resplendent in a double-breasted tuxedo and a batwing bow tie, summoning what the late Nelson Algren called ‘a rain that lightly rains regret’ and singing in his wonderful voice of the Tony Bennett verities — heartbreak, joy, and love, of course. Like no other.”