Tony Bennett is as cool at 90 years old as he was in his 20s and 30s. Maybe cooler.
That’s not lip service. It’s not like when you say to your grandpa, “You’re so handsome,” when maybe you’re just trying to make him feel good. Bennett is legitimately cool, at an age when it’s enough that you’re just walking around and able to pull on your own pants unassisted.
The way Bennett wears a suit, it doesn’t look like he’s heading to a funeral; it looks like he’s heading to a cocktail party that the rest of us aren’t hip enough to get invited to.
His coolness can’t be explained just by listing his accomplishments, but let’s do it anyway. 110 albums, 19 Grammy Awards, and 81 singles (including his biggest hit, “I Left My Heart in San Francisco.”)
Over the span of two centuries, he fought in the Battle of the Bulge during World War II, marched on Selma with Martin Luther King Jr., kicked cocaine using willpower alone, and sketched Lady Gaga naked for charity.
But it’s not the resume that makes him cool. It’s that he did it all without changing. He’s been doing the same thing, with the same smooth delivery and impeccable style, for seven decades. As Clint Eastwood once said, “Tony Bennett is cool because he doesn’t have to act like he’s cool.”
We caught up with Bennett as he heads into a particularly busy month—he’s got a new book out, Just Getting Started, and a two-hour TV special, Tony Bennett Celebrates 90: The Best Is Yet to Come, airing on NBC on December 20th at 9pm ET/PT.
Men’s Health: It’s difficult to imagine you in anything but an impeccably tailored suit. Is it possible that even your pajamas come with a tie?
Tony Bennett: They don’t come with a tie, but they’re nice, brand new pajamas all the time. [Laughs.] Being civilized is just important to me.
When was the last time you wore a grubby t-shirt and sweatpants?
Grubby? I’ll never wear grubby anything. But I exercise every day with a great trainer. So I’ll wear sweatpants for that. But then I take a shower and jump right back in the suit.
Do you just feel more comfortable in formal wear?
It’s something my mother taught me when we were very, very poor. She was a dressmaker, and she didn’t make much money, just a penny a dress. But she used to tell my brother and I, “Always have a clean suit jacket, a white shirt, and a black pair of pants.” That was important to her, and it became important to me. It changed my life.
She was seriously making a penny a dress? That seems ridiculous by today’s standards.
Who does anything for a penny anymore, right?
She was an amazing woman. She tried to make as many dresses as she could, because obviously every one counted. But when she got to a bad one, she’d throw it on the floor—I’ll always remember this—and she’d say, “I don’t work on bad dresses. Only the good dresses.” [Laughs.] I’ve tried to stay true to that.
You only wear good suits?
I only do good songs. The songs that are well written, and won’t be forgotten in ten months. You know them when you hear them. I never tried to get a hit record. You can’t do this for money. Money and fame comes and goes. It has to be about quality songs that you know are going to last forever.
You got your sense of style and your high standards from your mom. What’d you get from dad?
His voice. He was a great singer. Back in Italy, in Calabria where he grew up, my dad used to go up into the mountains and sing, and the whole valley below could hear it. Can you imagine that? No microphone, just the power of his voice.
Did you always want to be a singer?
Always. When I was ten, after my father died, my whole family — we had a lot of Italian relatives who lived nearby—they would come by the house every Sunday, to help my mom and just make her feel good. I would perform for them, and they would say, “I love the way you sing, I love the way you paint flowers!”
You painted too?
I painted and sang, my two passions. I sang for my family, for my mother, because I saw how happy it made them. I started singing in the courtyards, and the neighbors, they would throw me pennies. [Laughs.]
You were making pennies just like your mom.
It was a good life.
Do you paint as often as you sing?
I paint every day. When I paint, I become another person.
What kind of person?
A quiet person. [Laughs.]
You don’t get to be quiet all that often onstage.
Never. I love singing and entertaining people, but sometimes it’s just nice to sit and do nothing. When I paint, I concentrate on the one painting that I’m working on, and it’s quiet and lovely.
What’s your favorite subject for a painting? Do you prefer painting portraits, or landscapes, or something else?
Anything. I’ll paint anything. I love painting nature, but anything that’s alive has seasons. People are nature. That’s life. There’s no painter that’s as great as nature itself. I live right across the street from Central Park, and sometimes when I’m home I’ll go into the park early in the morning, before the public gets there, and I’ll paint nature. I love painting Central Park. There’s so much about it that’s just breathtaking.
So if somebody in New York got up early enough, they could go to Central Park and maybe end up in one of your paintings?
No! Don’t tell them to do that. [Laughs.] That’s the last thing I need.
Your first professional gig, as a teenager, was as a singing waiter?
That’s right. I was just 14, and I loved it.
14? That is young.
I used to take requests from the audience to find out what they really wanted to hear. And then I’d go into the kitchen and ask the other singing waiters, who were all Italian, “How does this song go? What are the words?” They would tell me the words and then I’d come right back out and sing it.
What kind of songs?
Love songs, whatever they wanted.
So you’re a 14-year-old kid, probably going through puberty, singing love songs to adults. Did your voice ever crack?
Oh I’m sure, now and then. But nobody starts strong. Even when I was booking at nightclubs, I wasn’t ready. I had some real masters, singers who had been around the block, say to me, “You’re doing okay, but it’s going to take seven years to learn how to do it right.” And they were accurate. It took exactly seven years.
Why seven years?
There’s so much to learn. I thought I was doing great, and then Fred Astaire took me aside, told me how to put a set together. He said, “Make a set that you think is perfect—every song feels essential—and then pull fifteen minutes out of it.” [Laughs.] That’s genius.
After all of these years, is one gig pretty much like another? Or do any of them stand out?
They’re never the same. Each one is different. It’s funny the things you still remember. There was one time in Chicago—it was years ago, maybe decades—I’m singing, and all of a sudden the audience just gasps. They’re like, “Wow!” Well, I think they’re raving about how good I was singing. But it turns out, one of the trumpet players behind me fell off his chair. [Laughs.] All that time, I thought I was killing it. But the damn trumpet player is doing pratfalls behind me.
You’ve played for British queens and U.S. presidents.
Eleven presidents. I’ve played for every U.S. president since Eisenhower.
And you’ve played at the Playboy Mansion.
Sure. I’m up for anything.
Do you play the same set for a president as you do for Hugh Hefner?
For the most part, sure. But I’ll mix it up, add a few songs in the moment. It depends on the room,
At the Playboy Mansion, did you pick songs that were extra sexy?
I did the opposite. I sang a song called “You Can’t Love ‘Em All.” [Laughs.]
You’ve performed some of the most romantic songs of all time.
Well thank you.
How many babies do you think were conceived by couples listening to “Fly Me to the Moon”
Um. [Laughs.] I couldn’t tell you. That’s their problem. I just sing it cause it’s a beautiful love song.
Frank Sinatra’s take on “Fly Me to the Moon” was arguably more famous, but in our opinion, your version blows him out of the water.
Oh no, no, no!
Come on, you can say it. Ol’ Blue Eyes had nothing on you.
I have so much respect for Frank. He always supported me, to the very last day of his life. He was always raving about me. He was a true inspiration. Everything Sinatra did was quality. Quality, quality, quality. I learned that from him. He was ten years my elder, and I tried to follow his blueprint.
But you never did movies like Sinatra. Why not?
I got talked out of it by Cary Grant, who became a great friend of mine. He came to my house, to buy one of my paintings, and we started talking about movies. I was thinking about taking a movie role, and he said to me, “Don’t do it. You’ll be so bored. It’s like prison.”
Prison? It’s that bad?
That’s what he said. He told me, “You just sit there all day, and then you do four lines and go home. It’s the worst.” He said I should travel the world instead, meet the public, make them feel good. And this is Cary Grant, right? The most handsome man in the world. So I think, maybe I should listen to him. [Laughs.]
You quit cocaine cold turkey in the 70s. What made you decide to stop?
Well, I was talking to Jack Rollins, who was Woody Allen’s manager for awhile, and we got to talking about Lenny Bruce. You know about Bruce?
Yeah. Brilliant comedian.
Right, right. Well, Jack knew Bruce when he was on top of the world. He was the best comedian out there, the talk of the whole business. And then he died. An overdose, I think it was. Jack said one sentence to me that changed everything. He said about Bruce, “He sinned against his talent.” That just blew me away.
You worried that you might doing the same thing?
I didn’t want to do the same thing. From that day on, I cut everything out.
I used to smoke a lot, and I stopped smoking. I stopped smoking dope, stopped the harder drugs. Stopped doing anything but taking care of myself, and being in good health.
How have you lasted this long?
As a singer or a person?
Because I like to make people feel good. That’s the secret to a long life.
It’s as simple as that?
That’s it. That’s it.
But surely some nights you’re just not in the mood? The last thing you want to do is sing “I Left My Heart in San Francisco” for the eight billionth time.
Doesn’t matter. It’s not about me. It’s never about me. It’s about them. I make sure the audience is having the time of their life when they come see me. It’s the only reason I wanted to do this with my life. When I was a teenager, I saw Jimmy Durante at the Copacabana (a New York nightclub) and he was so wonderful. I told my mother the next morning, “I’m going into show business,” and she said, “How come?” I told her about Durante, and how the people went crazy for him, and he made everybody feel so good. I wanted to be like that. I wanted to make people feel like Jimmy Durante made them feel.
It wasn’t about being as famous as Durante?
No. Never. It’s like Durante sang in that song. “Make someone happy/ Make just one someone happy/And you will be happy too.” [Laughs.] That’s it. That’s all there is. That’s all you need to know.
[This story originally appeared, in a slightly different form, in the December 2016 issue of Men’s Health.]