Here’s How Tony Bennett Knew ‘I Left My Heart In San Francisco’ Would Be a Hit

TONY BENNETT LIVE BY REQUEST: A VALENTINE'S DAY SPECIAL, Tony Bennett, 1997.
Automatic Productions/ Courtesy: Everett Collection.

Nearly nine years ago, I enjoyed a true highlight of my long career in writing about entertainment: I was offered an invite to Tony Bennett Celebrates 90: The Best Is Yet to Come, a star-studded celebration of Bennett’s 90th birthday that would be broadcast on NBC.

The birthday boy was much too busy chatting with and being serenaded by A-list musicians and actors to take questions that night at Radio City Music Hall. But a few weeks later, Bennett treated me to a nearly hourlong chat that ranged from his close friendship with Lady Gaga to his philanthropical efforts to his artwork and advice from some famous mentors.

Six years later, on July 21, 2023, Bennett passed away — but a few of his stories are still fresh in my mind. Particularly one about the charming way he knew his signature tune, “I Left My Heart in San Francisco” would be a hit.

Take it from the barkeep

Somewhere in the middle of our chat, I asked Bennett when he first heard a piece of music, a singer’s voice or a song that made him realize music would be his lifelong career.

“It’s so funny that you mentioned that,” Bennett exclaimed. “There is something that really happened in my life. We were in a Southern town, and rehearsing in the afternoon and there was a bartender setting up a bar for the evening’s performance. We found the song ‘I Left My Heart in San Francisco,’ and because we were going to San Francisco for the first time, we said, ‘Let’s do that song when we go.’

“As we were singing it, the bartender came up from behind the bar, and he said ‘I don’t mean to interrupt you guys, but if you record that song, I’m going to be the first one to buy that record,” Bennett continued of the George Cory/Douglass Cross song. “And that was the tipoff to ‘I Left My Heart in San Francisco.’”

Bennett did indeed record the song, thought it was only released as the B-side to “Once Upon a Time.” DJs ignored that tune, choosing to play “San Francisco” instead. It spent a year on various popular music charts and earned the Record of the Year Grammy in 1963. As proof of its timeless appeal, the song was also inducted into the Grammy Hall of Fame in 1994 and selected by the Library of Congress to be preserved in the National Recording Registry in 2018.

> Remembering Tony Bennett, 2 Years After His Death

 

Advice from Benny and Burns

Singer Tony Bennett In his New York Central Park West penthouse apartment painting studio in June 2002.

Eeddie Sanderson/Getty

Later, when our discussion turned to Bennett’s successful career as a painter, I asked the legend if music informed his painting or vice versa.

“When you paint, you learn so much about singing. When you sing, you learn so much about painting,” Bennett explained. “It’s knowing what to leave out, not what to put in. It makes the painting spontaneous and alive. … You leave it unfinished. It’s the same with music, and it’s the same with art. You keep it alive.”

Then Bennett shared the surprising sources of that “less is more” lesson — iconic comedians Jack Benny and George Burns.

“They met me when I first had hit songs with ‘Because of You’ and ‘Cold, Cold Heart.’ Million-selling records,” Bennett recalled. “They said, ‘Now son, [you] really hit there with these two songs, but it’s going to take you seven years to learn how to do it.’

“Boy, were they right!” Bennett chuckled.

Tell us about your favorite Tony Bennett tunes in the comments below!

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