On the day I meet Tony Bennett, a splendid summer afternoon in London, neither of us is to know that one particular song from his new album Duets II, a series of collaborations with stars ranging from Aretha Franklin to Lady Gaga, will soon overshadow the rest.
That song is "Body and Soul," a 1930 standard that he sings with Amy Winehouse. Talking about her to me, Bennett's face clouds over. "She's a great artist. I'd really like to help her, talk to her about slowing down, with the problems she's got," he says.
But that will never happen now. Not long after the veteran New York crooner's visit to London, Winehouse was found dead. "Body and Soul," a jazzy ballad on which she accompanies Bennett's warm tones with a statuesque slur, giving lines such as "My life, a wreck," the wayward flourish of a modern Billie Holiday, now carries the unwanted distinction of being her last official recording. Last month Bennett led the tributes to her at an MTV awards ceremony. "Amy had the whole gift, she sang beautiful," he said.
That fate should entwine the pair in this fashion is grimly ironic. Winehouse was only 27 and had two albums to her name. Bennett is 85 and Duets II is his 63rd album. Next month he will play a televised show at the London Palladium, with his old friend Cary Grant's words ringing in his ears: "He said, 'Make sure you play the Palladium because there's a lot of history there.' " No singer is better qualified to offer advice about artistic longevity than Tony Bennett. Few needed it more than Amy Winehouse.
Born in 1926, Bennett is one of the last survivors of the pre-rock-and-roll era of popular music. His first hit was the orchestral weepy "Because of You" in 1951. It was succeeded at No. 1 in the charts by Bennett's version of "Cold, Cold Heart," a cover of a Hank Williams song whose breezy pop makeover caused the volatile Williams to telephone Bennett complaining, "What's the idea of ruining my song?"
Bennett chuckles. "He said that with a sense of humor because it sold millions of records." It's July, two weeks before Winehouse's death, and we're at the Dorchester Hotel, in the lavish penthouse suite designed in the 1950s by the theater designer Oliver Messel. The walls are covered with smoky inlaid mirrors and green rococo decor mimicking an arbor. French windows open onto a spacious terrace balcony with a gurgling fountain and panoramic views over London.
It's a far cry from Bennett's Depression-era childhood in a small apartment above a sweets shop in Astoria, Queens. His father, a grocer, died when Bennett was 10, forcing his mother to become a seamstress to support the family. "My Mom had to raise three children and she was working on a penny a dress to put food on the table for us," he says.
Love of music ran in the family. His elder brother, who turned Bennett on to jazz, sang at the Metropolitan Opera as a teenager and was nicknamed "the little Caruso." Bennett's own beginnings as a singer were humbler. At 16 he began working as a singing waiter at an Italian restaurant in Queens, serenading diners.
"Irving Berlin and Frank Sinatra and myself, we were all singing waiters when we first started," he says. "You'd take an order, what food they'd want, and then I'd say, 'What song would you like me to sing?' and I'd take their requests." Bing Crosby's hit "I'll Get By (As Long as I Have You)" was a popular choice. "I loved the gig. I very clearly remember saying to myself, I may not become a popular artist but for the rest of my life I'm going to be a singer."
Seventy years later he shows no sign of flagging. Bennett's vocals still have an easy, mellifluous charm. He purrs through Duets II like a vintage Rolls-Royce, relaxed in the presence of younger guests from the worlds of pop, rock, and soul, who in turn seem eager to please him, as with Mariah Carey's uncharacteristically restrained turn on "When Do the Bells Ring for Me?"
"As you get older you get a bit of wisdom. You learn what to leave out, simplify things; it gets a little warmer, more natural, and less pushy. You just interpret a lot better as you get older," he says.
Like Sinatra, he's Italian-American, changing his name from Anthony Benedetto to Tony Bennett after being discovered by the comedian Bob Hope. In his singing you can hear the bel canto traditions of the old country slipping seamlessly into the vibrant, seductive new world of mass-produced popular music.
"No [other] country has ever given the world such a height of light entertainment, the most wonderful populist songs to fall in love with," he says. "It was a moment that will go down in history. In Britain they call it light entertainment but I'm convinced 35 years or 50 years from now it'll be called America's classical music."
Bennett came late to it. The golden age of the Great American Songbook, honed on Broadway and exported to the world by Hollywood, was fading by 1950 when Hope spotted Bennett singing in a New York nightclub. Nonetheless, he has proved one of its most loyal interpreters, sticking faithfully with the work of songwriters such as Jerome Kern, Irving Berlin, and Cole Porter, "who wrote better than anybody."
He continued making hits into the 1960s, with his best-known song, "I Left My Heart in San Francisco," coming out in 1962, while excursions into jazz with the likes of Count Basie gave him heavyweight kudos. In 1965, Sinatra said Bennett was "the best singer in the business."
"Well, what did he know?" Bennett says, an amused glint in his eye. His relationship with Sinatra was "always very respectful." "I was never part of the Rat Pack. I lived in New York and they were all in Vegas and Los Angeles but I was great friends with all of them."
Bennett was 9 when he first heard the 19-year-old Sinatra sing, on a radio talent show in 1935. Even then he was struck by Sinatra's confidence and, like every crooner of his era, he was destined to follow in the older man's steps. But there was no rivalry, he insists. "A rivalry happens when you're playing tennis or golf. In the music world there's room for everybody. I never wanted to be bigger than anyone else, I just wanted to be one of the best."
Bennett isn't an overbearing singer. He doesn't so much seize a song as elucidate it gracefully. "I never do a bad song. I don't like to insult the audience. I never do anything silly. I do very well-written songs." What's a "silly" song? "I don't know. I don't do 'em."
His fortunes dipped in the late 1960s as rock took over the music industry. Tony Sings the Great Hits of Today! found Bennett trying to get hip to the youth in 1970, but the results were as awkward as the garish psychedelic loon pants that the singer sports on the album artwork. "It's a nice album," he says unconvincingly, "but far from my favorite."
Bennett's refusal to make another crossover record led to his departure from Columbia Records. The 1970s weren't exactly wilderness years—he continued gigging, lived in London for a couple of years, launched a jazz record label—but the hits dried up. It wasn't until the late 1980s that he was rediscovered amid a revival of interest in the sharp suits, male bravado, and impeccable songcraft of the 1950s. Since then he's had a renaissance as the last of the great crooners.
"I could have retired 14 years ago. But I love it; it just gives me such a good feeling," he says, clapping his hands together. Does he feel like the last of an era? "I don't think of it that way. I do it because I love it. Years ago it was all about longevity. You got started and you had to keep learning a craft. My idols were George Burns and Jack Benny." Burns was still performing at 100. "I like that. I'm hoping that if I keep my health I can go that far."
It hasn't always been a smooth journey. When he was living in California in the late 1970s he developed a cocaine habit. "I went and took a dip. I thought I was doing great but when I was lucky enough to stop it, I really started doing well. I'd like to tell Amy Winehouse that's the way to do it. She's a very lovely person."
As we now know, his chivalrous hopes have been dashed. Winehouse has joined Frank Sinatra, Bob Hope, Cary Grant, Count Basie, and all the other ghosts from Tony Bennett's long and illustrious career.
This article originally appeared in Financial Times. Click here to read more coverage from the Weekend FT.