Steppin’ out with Tony Bennett

Tony Bennett, 85, sings with Amy Winehouse and Lady Gaga on his new CD, and has taken up sculpting. Try to keep up.
Steppin’ out with Tony
Photograph by Jessica Darmanin

“Bap! . . . Bap!” Tony Bennett’s unamplified voice, loud as a snare drum, bounces off the back wall of Place des Arts as he tests the acoustics at an afternoon sound check. Standing next to him at centre stage, looking out at the 3,000 seats that will be packed for his evening performance at Montreal’s jazz festival, I ask if some audiences are warmer than others. “The audience is never cold,” he says. “If they’re cold, that means you’re cold. You gotta walk out there energized. Sinatra taught me that years ago.” Energy? It’s not the word that comes to mind when you think of an old master crooning The Shadow of Your Smile or I’ve Got You Under My Skin. But when I gently broach that notion, Bennett gives me a puzzled look. Obviously I’ve never seen him perform.

That night, from the standing ovation that greets him as he bounds onto the stage to the one that bids him farewell, Bennett’s energy is miraculous. This, after all, is a man who would soon celebrate his 85th birthday on Aug. 3. His scuffed velvet voice seems enriched, not diminished, by age. Still muscular and elastic, it ranges from intimate jazz detours to flights of operatic grandeur—reminiscent of Sinatra, but infinitely warmer. Bennett works the microphone like a musical instrument, pulling it close for a confidential aside, but holding it just above his waist much of the time. At one point, he has the soundman turn off the mikes, then sings Fly Me to the Moon a cappella and unplugged, beaming his voice to the upper balcony. Near the end of the song, he opens the throttle. He hits a note, holds it, and his voice fills the hall like a floodlight, with a power that seems to come out of nowhere.

Oh, and he also dances. Occasionally, he’ll finesse a phrase with a pirouette, a switchblade flash of Vegas that draws a roar from the crowd. When his 37-year-old daughter Antonia comes onstage for a duet, Bennett joins her in a nimble soft-shoe. Throughout the show, he almost never stops smiling. And why not? His music, plucked from the Great American Songbook, summons up a golden age, when jazz and pop were happily married. Spanning Gershwin, Cole Porter and classic strains of Hollywood and Broadway, it exists in an emotional utopia—a wonderful world with skies of blue, where love comes just in time, little cable cars climb halfway to the stars on the sunny side of the street and the best is yet to come. It’s how America was meant to be.

Tony Bennett is the last torchbearer. He sang with all the legends and they became his friends—Louis Armstrong, Pearl Bailey, Bing Crosby, Fred Astaire, Ella Fitzgerald, Duke Ellington, Count Basie, Frank Sinatra, Nat King Cole, Judy Garland, Ray Charles. Now he’s the only one left standing. He works out three times a week, plays tennis, pursues a lifelong passion as a painter and recently took up figure sculpting—starting with a clay bust of Harry Belafonte, the man he calls his best friend now that Sinatra is dead. He’s been with his third wife for 26 years—they began dating when she was 19. Embracing his 85th birthday, he says, “It’s my favourite age right now. I love what I do. I’m never going to retire. I get up in the morning and the first thing I want to do is study music, or paint.”

Straddling several generations of jazz and pop, Tony Bennett has never been more fashionable. After weathering the rock ’n’ roll revolution and a ’70s slump in his recording career, he enjoyed an MTV-anointed comeback in the 1990s and has never looked back. To celebrate his 80th birthday, he recorded Duets with the likes of k.d. lang, Paul McCartney, Elvis Costello, Stevie Wonder, Céline Dion and Elton John. It sold three million copies. He went on to make a full album with k.d lang. And on Sept. 20, Sony Music will release Duets II, with an eclectic cast that includes Norah Jones, Sheryl Crow, Mariah Carey, Aretha Franklin, Willie Nelson, the late Amy Winehouse—and a fellow phenomenon born of New York Italian Americans, Lady Gaga.

Bennett met her at a benefit concert in Manhattan. “The first thing she said to me was, ‘Anything you want to do, I’ll do.’ ” Bennett proposed Anything Goes, but they settled on The Lady is a Tramp. “She sings very well and she knows how to swing,” he says. “She has that training you’re supposed to have. On the record, I’m hoping to show everybody. I want people to say: ‘I didn’t know she sang that well.’ ” In an age when it seems every pop star has to be a songwriter, Bennett, who isn’t one, has devoted his career to the art of interpretation, to rendering a song so well that he owns it. “It’s a lost art,” he says. “We try to do what Nat King Cole and Ella Fitzgerald tried to do—the definitive version of a song. That’s the game.” Bennett can’t talk music without paying homage to his idols, especially Frank. Sinatra crowned him as his successor as early as 1965, when he told Life magazine, “For my money, Tony Bennett is the best singer in the business. He excites me when I watch him. He moves me. He’s the singer who gets across what the composer has in mind, and probably a little more.”

Bennett’s story is as rich an embodiment of the American Dream as you will find. He was born Anthony Dominick Benedetto in Astoria, in the New York City borough of Queens. The son of impoverished Italian immigrants, he dreamed of being a painter. After losing his father at age 10, he worked as a singing waiter in his teens to support his mother, a seamstress who made dresses for a penny apiece. After fighting in Europe at the end of the Second World War—where he witnessed the horrors of a concentration camp—he resumed his assault on showbiz and studied the art of bel canto singing. He was discovered by Pearl Bailey and got his big break, and name, from Bob Hope. Tony had adopted the moniker Joe Bari, which Hope disliked. When the singer told him his real name, Hope said it was too long for the marquee and rechristened him Tony Bennett. (His paintings, which now sell for five figures and have penetrated the collections of museums such as the Smithsonian, are still signed Benedetto.)

The morning of his Montreal concert, Bennett has agreed to meet me at the Montreal Museum of Fine Arts. Several rooms, housing French Impressionists and Old Masters, have been closed to the public so he can roam undisturbed. Bennett says he paints every day. He has an apartment overlooking Central Park, which he’s painted countless times. He reveres studious technique in both art and music. His favourite artist is the 19th-century portrait painter John Singer Sargent. But we linger over the Impressionists.

Admiring a Matisse canvas of a woman seated by a window overlooking a sail-flecked promenade in the south of France, he says, “Even though it’s primitive, it really captures the light. It’s a sketch in oil.” So is a vocal line like a brush stroke? “Yes. It’s knowing when to stop, what to leave out. My ambition is to actually sound better as I get older. It’s all about meaning it more, giving it more depth. Being genuine.”

The first painting Bennett ever sold was called South of France, bought by his friend Cary Grant. “We became very close,” he says. “He told me, ‘Don’t do movies. It’s the most boring thing in the world. You get dressed at six in the morning, maybe you don’t do a line until five in the afternoon, and you spend the next six months thinking, why did I do that movie?’ ” Bennett starred in one film, a dud called The Oscar (1966). He was asked to do more, “but because I’m Italian American, they were all gangster movies. I didn’t want to put my race down. I’m the only guy who didn’t like The Godfather. I didn’t like The Sopranos. I don’t like that Jersey thing they’ve got going.”

After spending decades in nightclubs, Bennett has mixed with his share of wise guys, but the Mafia stereotype still rankles. In the time I spend with him, it’s the only thing that darkens his sunny disposition—aside from a long-standing grudge over the insult inflicted on American music by rock ’n’ roll.

That comes up after the Montreal concert, as Bennett holds court at 25,000 feet, not quite flying to the moon, but to Toronto in the leather-bound luxury of a private jet. I sit facing him, as in a railway car, straining to hear his soft, husky voice above the engine’s roar. It’s loud. Tony’s wife, Susan Crow Benedetto, a willowy blond with a quick intelligence, sits across the aisle with an iPad and a glass of red wine. As Bennett sketches me in a square-ruled notebook, we talk about how he’s resisted pressure to adapt to musical fashions. “When Elvis Presley became famous, good music died,” he says, quoting a favourite line by Fred Astaire biographer Joseph Epstein. “I have an education. I know the difference between a good song and ‘so what.’ ” Dismissing rock ’n’ roll as “white music,” he still hasn’t forgiven it for putting so many trained musicians out of work. Sure, he has recorded duets with rock singers, but always on his home turf of jazz standards.

Winehouse—who would be found dead three weeks after our interview—was already fluent in jazz. “She was really the best of all the young artists that I met in the current scene in the last 10 or 15 years,” Bennett told Rolling Stone. “She was singing true jazz . . . I wanted to talk her out of the drugs, but unfortunately I never had a chance.” When they recorded Body and Soul last March, Bennett told me, she didn’t know how to approach it until he mentioned Dinah Washington—“The minute I said that, she got it.” (Their duet is being released as a charity single.)

Among Bennett’s other Duets II cohorts, Sheryl Crow is “a good friend.” Willie Nelson “picks the best song he can think of, On the Sunny Side of the Street, and does it really simple. He doesn’t go way off the melody.” Paul McCartney “sings very well, [and] is sensible about things.” Bennett prefers him to the Beatles. I don’t dare ask about the Stones.

“I never wanted to be number one, only one of the best,” he says. “Being number one is treacherous. I’m not in that race. The best jazz artists are still ahead of the pack. They keep honing that gift, and it will never sound dated.” Bennett traces rock’s ambitions back to Liberace’s record-breaking performances at Madison Square Garden. “When the music executives saw how much money they could make, they went into ballparks and giant outdoor venues. The more people they got, they acted like they’re bigger than anybody. My answer to them is: Hitler had more people than that, and he was lousy.”

Though he resented rock, Bennett joined in other aspects of the ’60s revolution. He was active in the civil rights movement, and got swept up by the drug culture. “When I was young,” he says, “I did everything.” In 1979, worn down by financial woes and a cocaine habit, he almost died of an overdose; Sandra, his second wife, had to haul him out of a hot bath and pound his chest to get him breathing again. That was a wild marriage. All the Things You Are, a new biography by David Evanier, tells of her drunkenly stripping in the front row during a royal command performance in London, hurling her clothes onto the stage as Tony continued to sing. But by the 1990s, Bennett had got clean and found a financial saviour in his son Danny (one of four children), who remains his manager. He also found Susan. “This lady I’m with,” he says, “is so sane. I live a comfortable life. I eat well, I sleep well.”

It’s only fitting that she’s a San Francisco girl. I Left My Heart in San Francisco is Bennett’s signature song, first performed at the city’s Fairmont Hotel. Which is where he learned of his mother’s death, just before hitting the stage on Thanksgiving in 1977. He asks Susan to tell the story of how they met.

“I’m a fifth-generation San Franciscan, so I was born and raised on Tony Bennett,” she says. “As a little kid I grew to love his music, and my parents would take me up to the Fairmont to hear him. They had friends who knew him, so I would get backstage. As I got older, he was a little more interested in me getting backstage.” One time, she adds, “I innocently called him up and said, ‘Can I see the show?’ He said, ‘Sure, come on up and be my date.’ I dumped the guy I was having lunch with that day and here we are all these years later.” A former teacher, Susan has since worked with Tony to create the acclaimed Frank Sinatra School of the Arts in his old neighbourhood of Astoria.

“Susan,” says Diana Krall, “is one of the few women of my generation who knows as much about music as anyone I’ve ever met. She’s amazing.” After performing an outdoor concert in Toronto, Krall sits backstage, fretting about a duet she’s planning to sing with Bennett, who has just begun his set. Her voice trembles as she talks about him. “It’s so emotional to hear him right beside you,” she says, “which is why I’m a little flustered. You know that sound. It’s your mom, it’s your dad, it’s your childhood.” She remembers lying on the floor, being blown away by his album with jazz pianist Bill Evans. “Tony’s a jazz singer, but he’s not a jazz singer. He still gets choked up about San Francisco. He’s like a great actor. Very few people can do that without being nostalgic. Tony is not nostalgic. He understands the music because he lived it at the time the songs were being composed.”

Krall suggests I talk to her husband, Elvis Costello. While she sits at an electric piano, rehearsing her duet (The Best is Yet to Come), Costello, in shades and a straw fedora, recalls first singing with Bennett on a 1983 TV show with Count Basie. “I made a complete hash of it. I’d lost my voice singing rock ’n’ roll. You want to be in full voice when you’re singing with Tony Bennett.” Asked about Bennett’s disdain for rock, he says, “We have continual arguments about whether rock ’n’ roll swings, which of course it absolutely does. I have a different view of the Great American Songbook than Tony—it has Willie Dixon and Hank Williams in it. But I totally respect that for Tony it begins and ends when it does. Depending on where you started from, certain kinds of music must seem horrifying.”

Outside, Bennett is singing in the rain. Though the stage is covered, the crowd is getting soaked. They don’t seem to mind. But with thunder and lightning moving in, the promoters pull the plug. Krall’s duet never happens. And Bennett, who usually closes his show with a heartbreaking version of The Music Never Ends, has to cut his set short. In the long term, barring a force of nature, he sees no end to the music. “God forbid, if something happened and I couldn’t sing well, I would just paint for the rest of my life,” he says, with the tireless smile of a man who still believes the best is yet to come.