As we celebrate Volume Two of our History of the Music Biz, we bring you a few of the many memorable anecdotes from Michael Sigman's profile of the legendary Tony Bennett. (Click the cover image at left for a larger view.)

Tony explained how he got his big showbiz break. It was 1949, the year I was born, and Tony, using the name Joe Bari, had been knocking around small clubs like the Shangri La in Astoria, Queens. To his astonishment, the owner of the Village Inn, a classy Lower Manhattan supper club, invited him to open for Pearl Bailey, a huge star.

Tony recalls, “Pearl was doing two movies and a show on Broadway, and she was booked at the Village Inn. She had heard me sing and must have liked what she heard, because she went to the boss at the club and said, ‘I don’t work here unless this boy is on my show.’ The boss said, ‘Are you serious? We’re only booking you, and that’s costing us a fortune.’ She said, ‘If I can’t present him to the audience, I’m not performing here.’”

The formidable Bailey got her way, which led to a second astonishment: “Bob Hope came down to see the show, and afterwards he came over to me and said, ‘You’re coming with me. I’m taking you to the Paramount and on tour with me.’ I couldn’t believe it. This was Bob Hope!”

Hope did Tony another favor, one that would last a lifetime. “He asked me my name and I told him, ‘Joe Bari.’ He asked me for my real name and I said, ‘Anthony Dominick Benedetto.’ He said ‘That’s too long for the marquee; Let’s Americanize you and call you Tony Bennett.’”

In 1956, Tony was given the coveted summer replacement spot on NBC-TV’s Perry Como Show, a Saturday night institution. But the lack of network support made him anxious.

“They left me with very few guest stars and a bare stage instead of a big orchestra. On a hunch, I went to the Paramount Theatre to see Frank Sinatra. He was 10 years older than me and I idolized him at the time. Because I had the two top songs in the country, he knew who I was. So I went up to his dressing room and he said, ‘What is it, kid?’ I told him why I was in a panic and he said, “Just know that if there are people in the audience that came to see you. They’re friends; they’re not an enemy. They’re rooting for you, so you befriend them right back.’ That was the greatest lesson, and to this day I still have that philosophy. And I’ve sold out all over the world for all those years.”

“We were down south in Arkansas playing a club, and there was a bartender listening to us rehearse. After I sang it, he said, ‘I don’t want to interrupt, but if you record that song, I’ll be the first one to buy it.’ That was a tipoff that we should record it.”

The song, “I Left My Heart in San Francisco,” was released as the B-side of a show tune, “Once Upon a Time.” “I was working ‘Once Upon a Time,’ and a Columbia Records rep called me and said, ‘You have to turn it over.’ I said, ‘What do you mean?’ He said, ‘We’re selling this thing like you won’t believe because of the B-side, so you have to start promoting that.’

“Even Goddard Lieberson called to say how important that song was gonna be to my career. It was a real grass-roots phenomenon, and to this day it’s still my biggest song. I couldn’t believe it, ’cause I had never been in San Francisco!”

To order a copy of The History of the Music Biz Two: The Mike Sigman Interviews, go here.