In the 1950s, Mr. Bennett toured for the first time, played Las Vegas for the first time and got married for the first time, to Patricia Beech, a fan who had seen him perform in Cleveland. The marriage would founder in the 1960s, overwhelmed by Mr. Bennett’s perpetual touring, but their two sons would end up playing roles in Mr. Bennett’s career: the older one, D’Andrea, known as Danny, became his father’s manager, and Daegal, known as Dae, became a music producer and recording engineer.

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 moldering in a drawer for two years. Mr. Sharon and Mr. Bennett decided that 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 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 got sensational reviews — though The Times’s was measured — and the recording of the concert is now considered a classic.

But as the 1960s proceeded and rock ’n’ roll became dominant, Mr. Bennett’s popularity began to slip. In 1969, he succumbed to the pressure of 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 the Beatles’ “Eleanor Rigby” and “Something” — was a musical calamity, a record that Mr. Bennett would later tell an interviewer made him vomit.

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