In July 1961, Mr. Bennett was performing in Hot Springs, Ark., and about to head to the West Coast when Ralph Sharon, his longtime pianist, played him a song written by George Cory and Douglass Cross that had been languishing in a drawer for two years. Mr. Sharon and Mr. Bennett decided it would be perfect for their next date, at the Fairmont Hotel in San Francisco, and it was.

They recorded the song – of course it was “I Left My Heart in San Francisco” – six months later, in January 1962. It won Mr. Bennett his first two Grammys, for best male solo performance and record of the year, and worldwide fame. In “The Good Life”, he wrote that he was often asked if he ever got tired of singing it.

“I answer, ‘Do you ever get tired of making love?'” he wrote.

Just five months later, Mr. Bennett performed at Carnegie Hall with Mr. Sharon and a small orchestra. He received rave reviews – although that of The Times was measured – and the recording of the concert is now considered a classic.

But as the 1960s wore on and rock ‘n’ roll became dominant, Mr. Bennett’s popularity began to slip. In 1969, he succumbed to pressure from the new president of Columbia Records, Clive Davis, to record his versions of contemporary songs, and the result, “Tony Sings the Great Hits of Today!” — including “Eleanor Rigby” and the Beatles’ “Something” — was a musical disaster, a record that Mr. Bennett would later tell an interviewer made him vomit.

His relationship with Columbia soured and eventually ended, and in the mid-1970s Mr. Bennett formed his own company, Improv Records, on which he recorded the first of two of his most critically admired albums, duets with the jazz pianist Bill Evans. (The second was released on Evans’ label, Fantasy.) Together the two opened the Newport Jazz Festival, which moved to New York, at Carnegie Hall in 1976.

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