Tony Bennett and his daughter, Antonia Bennett, return on Friday, June 21, to the Ravinia Festival in Highland Park. Associated Press, 2018

40 times! Legendary crooner Tony Bennett returns to Ravinia stage

Tony Bennett, the musical legend, has led a storied career for nearly seven decades, performing with musical royalty, both past and present, and living out his creative dreams.

The jazzy, outgoing crooner and painter makes his 40th appearance at Highland Park’s Ravinia Festival Friday, June 21.

We spoke with him about his history, his collaborations and his art in an emailed interview:

Q. When did you feel like you made it? Do you remember the first time you walked on stage in front of thousands of people and thought “I belong here”?

A. In 1949 I was invited to go on tour with Bob Hope. He asked my name. I told him Joe Bari. He said, “What’s your given name?” I told him it was Anthony Benedetto. He said, “Well, let’s shorten it to Tony Bennett.” So Bob Hope introduced me on that stage at New York’s great Paramount Theatre! In 1951 Columbia signed me to a recording contract. I made “Because of You,” and my career really took off.

I felt that I had made it with my first hit record. A string of hits followed, along with the Bobby Soxers (screaming teenage girls). In 1962, when I recorded what would become my signature song, “I Left My Heart in San Francisco,” I received my first two Grammy Awards, and that song has made me “A Citizen of the World.”

My beautiful friend Pearl Bailey (who, along with Bob Hope, really discovered me) once said, “It will take you 10 years just to learn to walk across the stage!” Boy, was she correct! I always loved to entertain for an audience. I have actually been doing that since I was a child — though at the time it was my family. The love you give with your music is the love you get right back! I just love what I do and I’ll never retire.

Q. What do you think it is about your music that makes you such a timeless artist?

A. I only stay with the very best songs … the classics. My dear friend and mentor Frank Sinatra gave me some good advice long ago, “Always stay with the best music.” Not to go for the fads of the moment. The great Count Basie told me, “Why change an apple!” I am only a timeless artist because I have always stayed true to myself and the songs I sing are timeless. Just like one of my favorite tunes, “I’m Old-fashioned.”

Q. What has been your favorite musical collaboration? And who would you have loved to work with but never got the chance?

A. Singing with Lady Gaga and our triumphant “Cheek To Cheek” Tour and Grammy Award-winning album. We played two nights at Ravinia, and it was the fastest sellout in their (then) 110-year history.

“Lady” is brilliant at whatever she does, and I just love her.

I would love to make an album with Stevie Wonder … and there is still a chance!

In 1988, Tony Bennett gifted his original painting “Ravinia: Music Under the Stars” to the Highland Park venue. It’s available for viewing at Ravinia Festival.

Q. What came first: your visual art or your music? And how do you feel the two inform or influence one another?

A. When I was a child growing up in Astoria, Queens, my first musical influence was my father. He had a beautiful singing voice. In his native Calabria, Italy, as the family story goes, he used to sing on a mountaintop and the whole valley would come to hear him. My brother John Benedetto, who was just a few years older than me, also had a beautiful voice. When he was a youngster, he was known as “The little Caruso” and even sang at The Metropolitan Opera House. My mother, Anna, was so loved by her family, and they would all congregate at our house (aunts, uncles, nieces, nephews) and John and I would entertain them. They would tell me “We like the way you sing.” “We like the way you paint flowers.” I remember very clearly saying to myself, “This is what I want to do.” John soon grew tired of studying music and singing, but he liked to go into the Village and fell in love with the great jazz clubs. I would go with him. I wanted to do everything that my older brother did. That is how I became so fascinated with jazz.

My dear friend Duke Ellington once told me to “Do two things and not just one.” Singing and painting are my greatest passions. I want to do both and keep getting better and better as I get older.

Singing and painting are both creative art forms. One is done in front of an audience and the other in solitude. It is a beautiful balance in my life. Each one is an expression of who I am and what I am feeling at the moment. For me “Nature is the boss!” I especially like painting the stunning beauty that is nature and I try to paint or sketch every day. It is a quiet way to relax and have this time to myself before I go onstage.

Antonia Bennett joins her father Tony Bennett for the “I Left My Heart” tour at Ravinia Festival Friday, June 21. – Courtesy of Larry Busacca

Q. Do you have a favorite song?

A. I would have to say, “I Left My Heart in San Francisco.” You know my longtime gifted pianist, the late Ralph Sharon, found this song for me one day when we were playing the world-famous “Venetian Room” of The Fairmont in San Francisco in 1961. I recorded it in 1962 and received the first two of my 19 Grammy Awards. I sing it at every performance. … I love to promote San Francisco. I understand people have even traveled there from all over the world after hearing that song. It’s a magnificent city. I can’t wait to sing it every night!

• • •

Tony Bennett “I Left My Heart Tour” with special guest Antonia Bennett

When: 8:30 p.m. Friday, June 21 (doors open at 4:30)

Location: Ravinia Festival, 418 Sheridan Road, Highland Park, (847) 266-5100 or

Tickets: $39 for lawn, $126-$146 for pavilion seating

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