Tony Bennett on his first job, Sinatra's advice and San Francisco

As an aspiring young singer, Tony Bennett recalled a relative warning him that his voice was too raspy, and that he wouldn't make it in show business. It didn't stop him; in fact, the warning only sharpened Bennett's determination.

"John Barrymore once said: The harder the slap, the greater the artist," Bennett told Fresh Air's Terry Gross in 1991.

Bennett, who revealed his Alzheimer's diagnosis in 2021 and died July 21 at age 96, would go on to become one of the foremost interpreters and champions of the Great American Songbook, with a career that spanned eight decades. As for that rasp? He credits drummer Louie Bellson, husband to Pearl Bailey, with helping him overcome it.

"[Bellson] taught me how to breathe so that when I sing, the rasp is not heard at all," Bennett said. "And it's just a matter of breathing before a phrase that you sing."

That wasn't the only advice that helped shape Bennett's career. Born Anthony Dominick Benedetto in Queens, N.Y., the singer said he adopted his stage name at the suggestion of comedian Bob Hope, who happened to catch his act in a New York City club.

"[Hope] saw me on the show and got a big kick out of it," Bennett recalled. "He said, 'Let's Americanize you,' and changed [my name] to Tony Bennett."

Bennett's career was a notably varied one. He came to prominence in the 1950s with hits like "Because of You" and "Rags to Riches," and released his signature song, "I Left My Heart in San Francisco," in the early '60s. The following decade, he redefined himself as a jazz singer by releasing two albums of duets with pianist Bill Evans.

Younger audiences started to catch on to Bennett in the '90s, through his MTV Unplugged performance and his duet albums, which over the years included K.D. Lang, Amy Winehouse, Aretha Franklin, Stevie Wonder and Lady Gaga.

Speaking to Gross in 1982, Bennett explained his versatility as a form of experimentation: "I don't like being predictable. And I like to do different things. I was the first one to sing without a microphone in clubs," he said. "So I'll try things. And if they work, I leave them in."

These interview highlights come from interviews taped in 1982, 1991 and 1998.

On meeting Frank Sinatra backstage

Tony Bennett: I was warned, "Look out, he could be pretty tough." So I said, "No. But I love the way he sings. And I love him personally as a fan. I'm just going to go up and talk to him." I found out that it was just the opposite of what everybody said about him. He was just wonderful to me and sat me right down in his dressing room and gave me some wonderful advice about not worrying about being nervous because he said the public likes that. He said, "If you don't care, why should the audience care?" He said, "If you're nervous, they're going to see that you care. So they're going to root for you. And the more they root for you, the more you'll give back to them," he said. "And it'll just be fine." And it was wonderful advice.

Terry Gross: Do you feel that you learned things about singing from listening to Sinatra?

Oh, well, if you listen to one, it's thievery. But if you listen to everybody, it's research.

On interpreting songs

Is there any etiquette among singers about who records what tune. Like, could anyone record "I Left My Heart in San Francisco" after you recorded it? How many years did it take until someone was able to make a recording of that?

Well, see in the early '50s, when I recorded, there was still a semblance of ethics, because if Nat Cole had a recording, you just left it alone. You found your own. And it was quite a challenge 'cause he'd come up with some pretty good records.

If one looks to see what other people are recording and there's certain songs you don't touch, the only person I think now who would be in the same league with you would be Sinatra. Would you be paying attention to what other people were recording and seeing what was theirs?

To me, there is a game, and the game is to make it your own number somehow ... even if you have to change the tempo a little. If Sinatra's doing a tune that's a ballad, but you like it very much, you could swing it, or if there's a swing tune that you could turn into a ballad. So that it becomes your interpretation, your way of doing it. So there's a little originality. I'm very interested in people that are individuals, rather than all doing the same thing.

What makes a song right for you to sing? I mean, you have a wonderful repertoire, and your interpretation of certain songs have really made me hear them in a way I haven't before. How do you know that a song is one that you want to sing? What do you look for?

Sometimes I just migrate over to, like, what's autobiographical? Unconsciously, I'll just find something, and I say, "My God, I've experienced that. I've lived that. It's happened to me!" And it could be humorous. It could be dramatic. It could be smooth and cool. You never know which way it's going to come from, but what I really look for is a kind of craftsmanship in a song, someone who's really musically knowledgeable and combines it with great words, so that it meshes. And I like to concentrate on interpreting songs.

On his smash hit "I Left My Heart in San Francisco"

Did you know that "I Left My Heart In San Francisco" would be the overwhelming smash success that it was?

I had no idea about that one because I really thought that was a local hit, that in San Francisco the people loved their magnificent city. And I thought it would just be local in that area, having no idea it would ever break into an international song.

What goes through your mind when you sing it now?

I happen to like it very much. I had a great idol when I was younger and even now, Maurice Chevalier — the way he performed, his gregariousness. There's his spirit. His energy at his old age was something to behold. And he had a handle called Paris. And everything he sang about was Paris. And to me, San Francisco is America's Paris. So it's a wonderful song for people to dream by. A lot of times, they said it doesn't necessarily mean San Francisco to them — just something, some dream that they'd like to have happen. And it happens to have a nice musical structure to it. And I like the song. So I don't mind doing it. I have to do it wherever I play.

A lot of creative people say, "Don't you get tired of singing that?" And I retort by saying to them, "Do you ever get tired of making love?"

Tony Bennett

A lot of creative people say, "Don't you get tired of singing that?" And I retort by saying to them, "Do you ever get tired of making love?" So it's like that. I happen to love the fact that it's made me this popular. It's allowed me to be as creative as I want in any musical endeavor. So it's given me a great license to be established in an institution in the country. And I'm very grateful for that song.

On his first job as a singing waiter

Your father died when you were 9. How did your mother earn the money to bring up the children?

Well, she was an amazing lady because she was a seamstress. And she worked so hard and raised three children. My older sister helped her so much and raised two boys. And we just were very close. ... It was just the most beautiful home life that you could ever dream of. And it was different. It was sad not to have a father and very confusing. But it's funny — it just shows you when people love one another how many things really work out.

How old were you when you had to go out and work for a living?

I was about 15 when I first started. I started out as a singing waiter.

So you had to sing in between serving or sing while you were serving?

Well, yeah, both. It was fun. It was almost Chaplin-esque, because I had two Irish waiters. And they were great, jolly-type guys and always wanted to encourage me. And I'd get a request to sing "I'll Get By" or a song like that. And I'd run into the kitchen to get ... [and] they'd teach it to me just right on the spot. And I'd come out singing it. And I used to love doing that. It was just so much fun every weekend when I sang there.

Were you still thinking of yourself as the clown when you were performing then?

I've been very fortunate even before I was known internationally. I always had luck with audiences. Somehow or other, I always had a gift of communicating. And I've got very nice reaction and encouragement from the audience. So it was always a positive thing for me to carry on. And I had all kinds of jobs, though. I really wasn't any good at anything, except — I used to have just this craving that I had to become a singer.

On war

You were in the military in World War II.

I was in the infantry, yes.

So as punishment, you were supposed to find the wounded and the dead and bury the dead.

Yes.

How long did you have to do that?

For two and a half weeks. It was horrible. It's just a horrible thing in my life, and I've never gotten over it. And man's inhumanity to man is very important to me, personally.

How do you think you were changed by that experience?

Well, it definitely made me anti-war.

Roberta Shorrock and Danny Miller produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Zach Thompson adapted it for the web.