New Album

Tony Bennett Duets with Amy Winehouse, John Mayer, Lady Gaga, & More

The music legend on working with the late singer, painting Lady Gaga naked, and more on his latest album.

Jemal Countess / Getty Images

Over the course of his 60-year career, Tony Bennett has won 15 Grammy awards; earned his star on the Hollywood Walk of Fame; been a Kennedy Center honoree, and founded the Frank Sinatra School of the Arts, a public high school in Astoria, Queens. In 2006, he released Duets, on which he sang with everyone from Bono to the Dixie Chicks. It earned him several of those prized Grammys, and went platinum in an era when people barely buy CDs. No wonder that Columbia Records is now releasing another album of collaborations, the aptly titled Duets II, on which he pairs with Lady Gaga, Sheryl Crow, Aretha Franklin, John Mayer, Amy Winehouse, and Mariah Carey, among others. He spoke with The Daily Beast about overcoming addiction, being in the studio with the late Winehouse, and painting Gaga naked.

For this album, you’ve managed to get duets with everyone from John Mayer to Lady Gaga. Do you do most of the duets in studio with them or do you do that thing where something is sent from one place to another?

We went all over the world, and instead of them coming to us, we went to them, recording where they’re comfortable. We went to see Queen Latifah at the Charlie Chaplin Studio in Los Angeles. For Amy Winehouse, we went to Abbey Road in Britain, then came back and met Lady Gaga in New York.

What was it like working with Amy Winehouse?

She sang the way I was taught to sing. She was really a great jazz singer, the only one of her contemporary singers, as far as I was concerned. I grew up on Frank Sinatra and Nat King Cole and here was this young girl, 26 or 27 years old. I said “Finally. Someone singing the way singers should sing.” She did it so well.

And how was it in the studio with her?

It was wonderful. At first everyone was apprehensive about it, but I said to her, “You sound like you were influenced by Dinah Washington.” And that relaxed her. She said “That’s my goddess. That’s the one I aspire to [be] more than anyone else.” So she knew that I knew where she was at and what she was doing. And that made her sing naturally and she gave a great performance.

Did you get any sense she was on drugs?

None at all. She was completely sober.

And the famous Gaga?

That was a gas. I first met her when we did a benefit for Robin Hood Organization. I went backstage after and she was with her mother, her father, and her boyfriend. And I said to her, “I’d love to make a record with you.” And she said, “Anything you want to do. I’ll do.” And the thing that’s amazing is that she’s kept her word right down the line. A few days ago, Annie Leibovitz photographed her completely nude in my studio for Vanity Fair, and I paint also. And so, in the magazine, there’s going to be a spread of me painting Lady Gaga completely naked.

Wow, nice.

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Yeah, she’s very beautiful.

What did you make of her costumes?

She’s different. And that’s one of the tricks to staying around. When she recorded with me she had the most beautiful gown on, and the next day, she had the checkered glasses and the checkered piano. She rediscovers herself on a daily basis. There’s no one quite like her.

When’s the last time you asked someone for a duet and didn’t get it?

It never happened. The only one I regretted never being able to do a duet with was Louis Armstrong. I would have loved to have done that.

What’s the worst thing about being 84?

Nothing. But I’m 85.

You grew up in Astoria, and have lived in the city on and off for most, if not all of your adult life. Do you agree with those who say the city has lost some of its character as it has become more about money?

It’s always been about money; it’s the capital of the world, financially. It’s always been that way. It’s like the song “New York, New York.” If you can make it there, you can make it anywhere. It’s my favorite place in the world. I like it better than Rome or Paris.

Do you think you’d be able to do what you did in your career if you were just starting out now, with the music business being in the state it’s in?

It was a lot better then. I’m not just being nostalgic. You had Sinatra; you had Ella Fitzgerald and Billie Holliday; you had Duke Ellington, Count Basie, Dizzie Gillespie, Miles Davis. It was a great era. Now it’s about, “How many tickets can we sell?”

In 1979, you called your son, told him you’d developed a drug problem, and asked for help. What did you learn that helped you get over it?

Well, I was spending more than I was making, and he told me that I couldn’t do that. I could have retired 14 years ago had I not spent all that money. But I like performing and I like entertaining and making people feel good. When they feel good, I feel good. So I’ll never retire.