Cary Hoffman Wants You to Know My Sinatra

How one man's obsession with Ol' Blue Eyes turned into a PBS special, an Off Broadway show, and a new career.

By , Columnist
Forty years ago, in June 1971, Frank Sinatra announced his retirement.

Of course, Ol' Blue Eyes had had rough times before. Twenty years earlier, having overused his voice, damaged his vocal cords, seen new stars like Eddie Fisher arise to eclipse him, and failed on television, Sinatra'd fallen into despair. But like many champs, he couldn't resist a comeback. And two decades later, his next "retirement" in 1971 turned out to be anything but the final sayonara of the man with the golden voice. Heck, Sinatra didn't even record the now-iconic "New York, New York" until 1980.

Forty years ago, in 1971, Cary Hoffman, Queens-raised son of a lox slicer, had put his longtime Sinatra obsession on hold. Taking his inspiration from his idol, he'd developed a career crooning in small auditoriums in the Catskills, but by the late '60s he'd quit the stage. 
The young singer, whose uncles were New York studio musicians who had worked with Sinatra and many others, began working behind the scenes, as a songwriter, arranger, and promoter. In parallel with his hero, Hoffman had grown disillusioned with the ascendence of rock and roll and the passing of the age of the crooners.

Hard to believe there was a time when Hoffman, now starring in his own show, My Sinatra, in New York, actually threw away his Frank Sinatra records and embraced as best he could the new four-chord style of songwriting and the high-pitched singing dominating the airwaves. Not to mention the long hair.

"But I was lost musically, because of rejecting Sinatra and adopting this avant-garde rock stuff," he says. As a teenager he'd "gotten inside of that voice" and would always "fight to go back to crooning. I'd turn Little Richard's 'Tutti Frutti' into a Cole Porter song."

As we now know, Sinatra didn't just get under Cary Hoffman's skin, he made a permanent impression on the whole world, even well past his prime—and still today, 13 years after his death at 82. Hoffman, currently playing at the Midtown Theatre in an open-ended run, has some good ideas why. First, "Sinatra became ultimately more than just about the music.  Like the Beatles and Bob Dylan and Elvis, anybody who becomes an icon transcends the recordings. Sinatra is a lifestyle."

Hoffman points to some young men in suits near us in the Wall Street area restaurant where he and I met for lunch. "A lot of these young business guys would like to have Sinatra's lifestyle. They'd love to smoke without any fear of cancer, to drink, fuck…That persona, I believe, has kept him alive because he is Mr. Cool. [Even] Bono and Springsteen say he's the coolest.

"And there was something else. In the music he said 'fuck you' also. See, rock and roll guys have to actually say 'fuck you.' But Sinatra said it by his attitude: This is what I want to do, and no one will stop me, and if I want to say 'babe' in the middle of a record…" So what if Cole Porter hadn't put "babe" in the lyrics? If Sinatra wanted to throw in a "babe," who was to stop him?

Adds Hoffman, "Sinatra was in some ways the first singer-songwriter. He didn't write them, but he changed them like he was writing them. When Sinatra was at his best he reinvented all those songs." Hoffman opens his show with "South of the Border" and says that when Sinatra sang a song like that, "it became a story that you believed": "Then she sighed as she whispered 'manana'/Never dreaming that we were parting/And I lied as I whispered 'manana'/'Cause our tomorrow never came."

Sinatra's tomorrows did keep coming, of course; his ability to fuse the tough-guy persona of his second-stage career with the rich emotion of his singing made him unique, which is part of why his music still speaks even to young people today. Just this week a dreadlocked 36-year-old car washer named Landau Eugene Murphy blew away the judges on America's Got Talent with a smashing performance in Sinatra's voice. A pair of boots once owned by Sinatra just sold for $2,500 at auction.

My Sinatra grew out of Hoffman's PBS special from a few years ago, produced by Jon Small (Billy Joel, Elton John, Garth Brooks). Public television also plans to air a Sinatra legacy concert by Michael Feinstein next month. The Chairman of the Board shows no indication of laying down his gavel any time soon. Move aside, Howard Stern; in the 21st century, Frank Sinatra has become King of All Media.

"It's like Vic Damone, Mel Torme, Peggy Lee, Ella Fitzgerald never existed to young people," says Hoffman - whereas Sinatra is still a pop star. "The way he's survived is bizarre. There's two books every year, two albums every year. It is amazing how it has lasted. Even ten years ago it wasn't as popular as it is now. You hear him in every bank, every coffee shop."

And you can hear him today, four times a week in a Times Square theater, in the surprising shape of Cary Hoffman, a self-described "Medicare recipient who looks like a rabbi." "It's not an impersonation," Hoffman is quick to point out. It's the story of an obsession—but a rewarding one for audience members. "I feel very romantic when I look out at the audience and I see these people, some of them with their eyes closed, singing along," he says. "I'm helping to put them in a place that was safer and more comfortable than now."

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Jon Sobel is a freelance writer, web editor, theater and music critic, marketing writer, and musician. His newest project is the blog Park Odyssey, where he is visiting and blogging every park in New York City - over a thousand of them.

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