The first thing I notice when speaking to Tony Bennett is, of course, his voice—languid, velvety, and still boyish, with an unmistakable cool cat vibe that’s probably been with him since the ’60s, when he was hanging out with Frank and all the other great ones. Tony Bennett hasn’t even sung a note, but it’s immediately clear I’m talking to one of the last great American voices.

The son of an Italian-born immigrant, Bennett’s first big break came back in 1949, when Bob Hope saw him working with Pearl Bailey in Greenwich Village and said, “Come on kid, you’re going to come to the Paramount and sing with me.” Hope suggested the young Anthony Benedetto shorten his name to Tony Bennett, and a star was born.

Songs like “Because of You,” “Rags to Riches,” “The Good Life,” “Who Can I Turn To (When Nobody Needs Me),” and his signature hit, “I Left My Heart in San Francisco,” earned him 15 Grammy Awards, including the prestigious Grammy Lifetime Achievement Award. In 2005, Bennett, who has performed for 10 U.S. presidents, became a Kennedy Center Honoree, and in 2007, his prime time special, Tony Bennett: An American Classic, won seven Emmy Awards.

Now entering his seventh decade as a recording artist with more than 100 albums, Tony Bennett will celebrate his 85th birthday with—what else?—a new CD. Tony Bennett: Duets II will be released September 20 on RPM/Columbia Records, but before that, Tony Bennett will celebrate another milestone: his 30th season at Ravinia, which will be marked with an 85th birthday concert on August 26.

On a recent busy day, which found Bennett visiting the school he founded in Queens 10 years ago, Bennett called me, with NYC sirens blaring in the background, to talk about his astonishing career, his friend Frank, and his secret for staying young.
 
On His Early Years

When Bennett was just 10, his father, newly emigrated from Italy and working as a grocer in Queens, died—leaving his mother alone to raise three children during the Great Depression. Bennett quickly went to work, helping to support the family as a singing waiter, among other things. If it was hard, he never noticed; in fact, he says it was one of the best times of his life. “The whole [extended] Italian family would join us every Sunday and make my mother feel so good,” Bennett says. “They’d make a circle around my brother, sister, and me, and we would entertain them. And they were so encouraging to us that they actually created a passion in me that I’ve never gotten over.”

Bennett says his family’s encouragement fueled him to pursue his two passions—painting and singing—but it was actually his service in World War II that gave him the break he needed. After the war, Bennett enrolled under the GI Bill at the American Theater Wing School, a place that launched such greats as Sidney Poitier, Marlon Brando, and Harry Belafonte. “The school was magnificent—the best teachers that you could ever dream of were there,” Bennett remembers. “I had very good training.” One of the things he learned was the Italian bel canto singing method, which Bennett calls “the art of beautiful singing” and what critics say has allowed him to preserve his voice over the years.
 
On Being an Artist

Although Bennett is now enjoying the sunset of his career, he’s had some bumps along the way—two divorces, a drug problem, financial troubles—but his dedication to his art has carried him through the rough spots. “I have a quote by Duke Ellington framed in my art studio,” Bennett says. “It says, ‘Number one: Don’t quit. Number two: Listen to number one.’ That’s the wonderful things about the arts—no matter how much you learn, it’s always like starting over again. You can never really say, ‘I’m an artist.’ You just say, ‘I’m getting better slowly. I still have this and that to learn.’ They say Leonardo’s last words were, ‘Has anybody ever finished anything?’”

A dedicated painter, Bennett has been commissioned twice by the United Nations and has three paintings in the Smithsonian Institution collections, including portraits of Ella Fitzgerald and Duke Ellington. “It’s funny, because painting is the same format [as singing],” Bennett says. “It’s all about learning what to leave out and how to simplify something so that it communicates. On the stage, don’t stay on too long, you’re gonna bore people if you do that. It’s the same with a painting. If you do something with a few lines, it’s worth a thousand words.”
 

On Frank

Tony Bennett was friends with all the greats—Ray Charles, Cary Grant, Nat King Cole, Bob Hope, Louis Armstrong, Judy Garland, Count Basie, Duke Ellington, Fred Astaire—but it was Frank Sinatra who really changed his life. “Frank Sinatra was doing a self-portrait in LIFE magazine (1965) where he really revealed how he felt about everything,” Bennett recalls. “He said, ‘For my money, Tony Bennett is the best singer in the whole business, and he excites me when I watch him perform. He moves me.’ It just changed my whole career, because his mass following automatically said, ‘Let’s check this out.’ From that day on, I’ve been sold out all over the world.”

Bennett never forgot what Frank Sinatra did for his career, so when he decided to establish a public arts high school in his hometown of Astoria, Queens, he named it the Frank Sinatra School of the Arts. In a letter on the school’s website, Bennett says, “I can think of no better way to remember, celebrate, and honor my best friend and colleague, the great performer and entertainer, Frank Sinatra, than to create a wonderful, vibrant school in his name.”

On Staying Young

At 84, Bennett shows no signs of slowing down—in fact, he has no plans to retire at all. “If you take care of yourself, you can get better as you get older,” says Bennett, who works out three times a week with a Romanian trainer, plays tennis, and eats well. But his real secret seems to be his ability to honor the past, enjoy the present, and look toward the future. “I sing and paint and love what I do every day,” says Bennett, bursting with pride after paying a visit to the Frank Sinatra School of the Arts. “I was so knocked out with the work that the students were doing, it’s unbelievable. It’s so exciting to be around them, to see what great work they’re doing already. The school is so successful, this is our 10th year, and 97 percent of the kids go on to college.” In addition to the school, Bennett and his wife, Susan, a former teacher, have established Exploring the Arts, a charitable organization that supports arts education in New York City public high schools. “Our dream is to go to every public school in the country and make sure they have an arts program,” says Bennett.
 
On Music

With very few exceptions, Bennett has stayed true to the music that inspires him: the great American standards. “That’s the kind of music I fell in love with,” Bennett says. “The ’20s, ’30s, and ’40s with Cole Porter, George Gershwin, Johnny Mercer, and all the great composers—that whole era is magic.”

His new CD, Tony Bennett: Duets II, a follow-up to the Grammy-winning best-selling CD, Tony Bennett Duets: An American Classic, once again features Bennett singing from the Great American Songbook with an all-star roster that includes Andrea Bocelli, Michael Bublé, Mariah Carey, Natalie Cole, Sheryl Crow, Josh Groban, Faith Hill, Norah Jones, k.d. lang, John Mayer, Willie Nelson, Alejandro Sanz, Carrie Underwood, and Amy Winehouse.

To make the CD, Bennett traveled all around the world to the homes of the artists he collaborated with, an ambitious project that is the subject of an upcoming documentary. While such an exhaustive schedule might be challenging for someone half his age, Bennett insists he’s having fun. “I’m just blessed,” he says.

Among his many blessings, he says, is his signature song, “I Left My Heart in San Francisco,” a song that, simply put, changed his life. “Internationally, it’s so loved,” Bennett says. “People dream about coming to America and visiting San Francisco because of it.” The song gained national exposure when Bennett performed it on television for the first time in 1962, on the first night of The Tonight Show Starring Johnny Carson.

“That was great,” Bennett says of the experience. “I’ll never forget, at the end of the show, Johnny Carson got up and said, ‘Well, that’s the first one. Let’s see what happens.’”