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Back Stories: My 2016 Interview With Tony Bennett

The iconic vocalist on his longevity, the secret to collaborating & much more.

In the summer of 2016, Sony Music Canada sent me to New York City for several days so I could sit down for a chat with living legend Tony Bennett and cover his 90th birthday celebration at Radio City Music Hall. This seems like an appropriate time to pull it out of the archive, along with my coverage of the event itself. As usual, I’ve added some bits that were edited out due to print space restrictions back in the day. Enjoy:


NEW YORK CITYTony Bennett is still going strong. And he isn’t going anywhere. “I’m not retiring at all,” the legendary crooner promises in an exclusive in-person Canadian interview. “In fact, I feel like I’m just starting out.”

Not bad for a guy who’s celebrating his 90th birthday. And fittingly, he’s celebrating it in a big way. The singer born Anthony Dominick Benedetto is marking his latest milestone with a slate of events and releases, including the memoir Just Getting Started, the star-studded two-hour TV special Tony Bennett Celebrates 90: The Best is Yet to Come, and a companion box set of the same name with Bennett classics and rarities alongside new tributes by the likes of Michael Buble, Andrea Bocelli, Diana Krall, Rufus Wainwright, k.d. lang, Stevie Wonder, Elton John and Bennett’s BFF Lady Gaga.

A few days before taping his birthday special at Radio City Music Hall, the casually dapper Bennett sat down in the Artist Lounge of Sony Music’s Manhattan HQ to rewind his illustrious career.

How does it feel to be an American institution?
(Laughs) It feels wonderful. You know, as a performer, you hope to be accepted. And to be accepted so fully for so many years … I’m thrilled at the fact that I’ve been performing my whole life. And I’ve been sold out my whole life. The audiences have been wonderful to me throughout the world. So it’s a wonderful accomplishment to me personally.

Do you like these big occasions and all the fuss?
Well, you just hope that everything works out. And you adjust to the amount of time they want from you and what they want to do with it. It’s always very interesting to create these events and to try to make them spontaneous and presentable to the public.

But on a personal level, is there any stocktaking from these milestones?
Oh yeah. There are many moments you remember. You remember the good things that happened, and you reflect on that.

Do you only remember the good things?
Well, no. You also remember the negative things and the things that didn’t happen. There’s moments you never forget — and moments you wish you could forget. (Laughs). But the majority of it has been very special for me. I’ve had the opportunity to participate and create with great artists.

Yes, you’ve collaborated with countless performers. What’s the trick to collaborating with someone?
You hope that when you do something with someone, it’s just for the right amount of time so it doesn’t bore the public. Sometimes, there have been occasions when it would go on a little too long. And then I’d have to make an excuse and say I have to go somewhere and just leave. (Laughs)

You’re not going to do that on me, are you?
Well, we shall see. (Laughs)

Speaking of moments you wish you could forget: Do you remember your 1970 album Tony Sings the Great Hits of Today?
No. I don’t remember that one.

You sang a bunch of pop songs. At the time it was panned, but today, it would probably be a hit.
You know, I never tried to get a hit record. I just wanted to do quality work. And I was fortunate enough to do that throughout my career. If somebody listens to one of my recordings, it doesn’t sound old-fashioned. It could have been done 40 years, but it sounds the same as if it were done today. That’s because I always did something with a jazz presence, and my involvement with the different people I’ve performed with makes it look like it’s not old-fashioned.

Is there a secret beyond that in terms of your career longevity?
Well, I love what I do. And again, I just make sure I don’t stay on too long. I don’t want to bore the public. So I make sure that whatever I do, it’s a statement that works. And then I say, ‘That’s it.’ And sometimes someone says, ‘Why don’t we do more of this or that?’ But I say, ‘No, that explains it.’

Is it hard to find that line?
No. Instinctively, you know where it is. Sometimes, it should just be a good 10 or 15 minutes. Sometimes it could be 3/4 of an hour with someone very special.

You have a new memoir. Tell me about that.
When it comes out, I think a lot of people will be very pleased with that book. It’s all about the different moments in my career and things that happened. Every chapter is dedicated to a certain person or place that influenced me. So there’s a chapter about Bob Hope and one about Judy Garland. Amy Winehouse is in there and Lady Gaga. It’s a mix of biography and people that have helped me and influenced me in my career. It’s a love letter to all these people.

And you have a new box set called Tony Bennett Celebrates 90. When you listen to those old songs, what goes through your mind?
I’ve never made a bad record. (Laughs) Even when what I was doing wasn’t the fashion at the time. When The Beatles or somebody came along, and their sound overtook everything else, well, I accepted that and was influenced by it. But I just kept on doing my own thing, you know. I just love jazz. I was influenced by Louis Armstrong and Billie Holiday and Ella Fitzgerald and Nat King Cole. And of course, my biggest influence was Frank Sinatra. He was a big fan of mine and always said good things about me. That was a wonderful compliment coming from him. Because he was absolutely the best.

What kind of music do you listen to now?
I listen to all kinds of music. I like a lot of classical performers. I’m always amazed by how much talent there is in the world. It’s amazing.

Do you like opera?

Have you ever thought about trying it?
No. I sang at the opera house here in New York — only once — and I was frightened because I was out of my element. But I was received so well it was unbelievable. In fact, the management of that institution still says, ‘We’d like for you to come back and perform.’ And I’m always surprised because O’m a jazz singer. But they liked what happened there that night.

You say you still enjoy touring. A lot of artists say that aside from the time onstage, touring can be a grind.
Well, they should get out of the business. (Laughs) I stay in the best hotels in the world. I play in the finest concert halls. I play beautiful halls — 2,400 seaters. To me that’s still a lot of people. I don’t play big stadiums. I’m not trying to play to 24,000 people. Other people do that, and it’s big business. But I’m not trying to make more and more money. I retired years ago, financially. So now, I just play nice, intimate halls that are acoustically perfect. And I’m surrounded by great musicians that play beautifully and inspire me.

Even so, with some songs that you’ve been singing for decades, it must be tough for your mind not to wander and start thinking about what you want for dinner?
(Laughs) I don’t think that way. If a song becomes boring to me, I take it out of the book. I only do songs I’m interested in doing. I don’t want to insult the audience. I don’t want to feel bored about anything I’m doing. So I just do songs I like.

Where do you wanna be on your 100th birthday?
I have no idea. We’ll have to wait and see. I just know what I want to do right now — I want to do what I love. And it’s very wonderful to be accepted throughout the world. I can’t ask for more than that, really.

•          •          •

NEW YORK CITY — When you turn 90 — and you’re Tony Bennett — you get a standing O just for showing up at your own party.

At least, that’s how it went when the iconic crooner arrived at the Radio City Music Hall taping of his birthday tribute special Tony Bennett Celebrates 90: The Best is Yet to Come. But the man of the hour wasn’t the only familiar face in the house: Umpteen famous friends, fans and fellow celebs were on hand to sing his praises. Some highlights from the night:

Alec Baldwin

Donald Trump’s favourite actor resurrected a different SNL favourite — his outsized Bennett impression — to add some comic relief. “I know my birthday was a couple of years ago … a couple of months ago,” he rasped. “But when you’re 90, every day above ground is a cause for celebration.” Tony even got in on the gag, playing Bennett impersonator Phony Bennett.

Lady Gaga

Tony’s recent collaborator and new bestie paid loving tribute to the crooner in word and song — first belting a swinging version of The Lady Is A Tramp in front of a 40-piece big band, then returning to purr a mesmerizing La Vie en Rose after talking about how he saved her career, helped validate her as an artist, and is her first call for dating advice.

Kevin Spacey

Anyone who’s seen his Bobby Darin biopic Beyond the Sea knows Spacey can carry a tune and hold his own. As he proved once again by wowing the crowd with his version of The Very Thought of You — after complimenting Bennett as a “master.”

Rufus Wainwright

While many of the performers swung for the fences, Wainwright went predictably lush and languid with his rendition of I Can’t Give You Anything But Love.

k.d. lang

Barefoot as usual and clad in what appeared to be black PJs, the chanteuse serenaded Bennett with A Kiss to Build A Dream On, a number from their Grammy-winning 2002 album A Wonderful World. When you’ve got a Grammy you can wear what you want, I guess.

Stevie Wonder

Bennett covered Stevie back in the ’60s — and they teamed up on Tony’s 2006 Duets disc. So no wonder Wonder showed up for the gig — and brought down the house with Sir Duke, a funky Happy Birthday, and a reworked I Just Called to Say I Love You.

Tony Bennett

The man himself closed his own party with a five-song set that included The Best is Yet to Come, I Got Rhythm and (of course) I Left My Heart in San Francisco — wrapping as always with his a cappella rendition of Fly Me to the Moon. “This is the greatest thing that has happened to me in my career,” he told the crowd. “Tonight is something that will live in my mind forever and ever.”