Bennett often said his lifelong ambition was to create “a hit catalog rather than hit records,” which he accomplished through more than 70 albums, garnering 19 Grammys — all but two after he reached his 60s. If his singing and public life lacked the emotional drama of Sinatra’s, Bennett appealed with an easy, courtly manner and an uncommonly rich and durable tenor that made him a master of caressing a ballad or brightening an up-tempo number.

“I enjoy entertaining the audience, making them forget their problems,” he told the AP in 2006. “I think people … are touched if they hear something that’s sincere and honest and maybe has a little sense of humor. … I just like to make people feel good when I perform.”

Bennett received many accolades from fellow singers, but none so meaningful than when his friend and mentor Sinatra said in a 1965 Life magazine interview: “For my money, Tony Bennett is the best singer in the business. He excites me when I watch him. He moves me. He’s the singer who gets across what the composer has in mind, and probably a little more.”

In 2014, at age 88, Bennett broke his own record as the oldest living performer with a No. 1 album on the Billboard 200 chart for “Cheek to Cheek,” his collaboration with Lady Gaga. Three years earlier, he topped the charts with “Duets II,” featuring such contemporary pop stars as Gaga, Carrie Underwood, and Amy Winehouse in her last studio recording.

For Bennett, one of the few performers to move easily between pop and jazz, such collaborations were part of his crusade to expose young audiences to what he called the Great American Songbook.

“No country has given the world such great music,” Bennett said in a 2015 interview with Downbeat Magazine. “Cole Porter, Irving Berlin, George Gershwin, Jerome Kern. Those songs will never die.”

Ironically, it was two unknowns, George Cory and Douglass Cross, who provided Bennett with his signature song when his career was in a lull. They gave Bennett’s musical director, pianist Ralph Sharon, some sheet music he forgot about until he was packing for a tour that included a stop in San Francisco.

“Ralph saw some sheet music in his shirt drawer … and on top of the pile was a song called ‘I Left My Heart In San Francisco.’ Ralph thought it would be good material for San Francisco,” Bennett said. “We were rehearsing and the bartender in the club in Little Rock, Arkansas, said, ‘If you record that song, I’m going to be the first to buy it.’”

Released in 1962 as a B-side, it became a grassroots phenomenon, staying on the charts for more than two years and earning Bennett his first two Grammys, including record of the year.

At times, Bennett struggled with recording companies for the right to sing the music he loved, but he refused to compromise by singing “cheap songs” that pandered to the latest musical fad. That approach served him well in a career that saw him become one of the only artists to have albums chart for seven decades.

After turning 60, Bennett could have accepted lucrative offers for extended runs performing old hit for older fans. Instead, his son and manager, Danny, found creative ways to market the singer to the MTV Generation without compromising his musical integrity.

“I wanted to be able to bring my music to as many people as possible, regardless of their age,” the singer wrote in his 1998 autobiography “The Good Life.” “I wanted to be one of the keepers of the flame when it came to great music. I knew that if I brought the best songs and the best orchestrations to people, they’d respond to it, because great music transcends generations.”

He appeared on “Late Night With David Letterman” and was a celebrity guest artist on “The Simpsons.” He wore a black T-shirt and sun glasses as a presenter with the Red Hot Chili Peppers at the 1993 MTV Music Video Awards, and his own video of “Steppin’ Out With My Baby” ended up on MTV’s hip “Buzz Bin.”

That led to an offer in 1994 to do an episode of “MTV Unplugged” with special guests Elvis Costello and k.d. lang. The resulting album won two Grammys, including album of the year.

Bennett would go on to win Grammys for his tributes to great female vocalists (“Here’s to the Ladies”), Billie Holiday (“Tony Bennett on Holiday”), and Duke Ellington (“Bennett Sings Ellington — Hot & Cool”). He also won Grammys for his collaborations with other singers: “Playin’ With My Friends — Bennett Sings the Blues,” and his Louis Armstrong tribute, “A Wonderful World” with lang, the first full album he had ever recorded with another singer.

It culminated with “Duets: An American Classic” in 2006 celebrating his 80th birthday. Barbra Streisand, James Taylor, Paul McCartney and Stevie Wonder were among those who recorded with him in his preferred manner — face-to-face in the studio.

“They’re all giants in the industry, and all of a sudden they’re saying to me you’re the master,” Bennett told the AP in 2006.

Bennett may have sung about San Francisco, but his heart belonged to Astoria, the working-class community in the New York borough of Queens, where he grew up as Anthony Dominick Benedetto during the Great Depression. The singer chose his old neighborhood as the site for the “Fame”-style public high school, the Frank Sinatra School of the Arts, that he and his third wife, Susan Crow Benedetto, helped found in 2001.

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Gans, the principal writer of this obituary, is a former Associated Press journalist. AP National Writer Hillel Italie contributed to this story.