"Frank Sinatra Has a Cold," Gay Talese's legendary literary shadowing of Ol' Blue Eyes, has long been enshrined in the pantheon of great journalism. This fall, the oft-anthologized piece will receive yet another honor when Esquire, where it originally appeared in April 1966, hails it as the greatest story ever to run on its pages.
The article appears as an insert in the October issue as part of the magazine's four-month celebration of its 70th anniversary, a packaging that goes far in showing just how much the magazine, and the industry of which it's a part, has changed.
For one, this hallowed piece of journalism now has a corporate sponsor - Absolut Vodka. Talese's article was chosen not only because it's an object lesson in how to translate a larger-than-life personality, but also because its subject still resonates.
"It's a very unique, modern marketing platform that drove that," says Esquire publisher Kevin O'Malley. "There's no advertorial, convoluted art direction, or Absolut bottle on the cover. Absolut took a very pure approach. They said this is an amazing story. It's on a great icon of entertainment and entertainment is a way to connect to our audience. From P Diddy to Dr. Dre to white-boy performers - [they] still reference Frank. He's still the 'Chairman of the Board.'"
The keepsake insert isn't the only nod Esquire is making to a journalistic pedigree that includes Hemingway, Mailer, and Tom Wolfe. The October issue will also include the 70 greatest sentences to appear in Esquire, a feature that's tailor-made for attention spans that won't go through the dense articles that made Esquire's literary reputation.
This is all part of a sophisticated package that includes a fashion spread that looks back at the past seven decades and the Esquire apartment, a 5,800 square foot, $19 million abode in the Trump World Tower, the world's tallest residential building, which will give advertisers the opportunity to put their wares in front of "key influencers."
O'Malley would prefer to talk about the magazine's service journalism rather than long-form articles. And, despite the nature of Esquire's celebration, he'd rather talk about the future than the past. The overall theme of the anniversary is the future of man.
Esquire, of course, isn't the only title trying to figure out what that future is by thinking younger. A recent New York Times article on GQ's first issue under its new editor featured this assessment: "GQ has responded to a midlife crisis by filling its magazine with shorter articles, hipper fashions, and a voice that suddenly seems 20 years younger."
Much of the same could be said for Esquire.
"Whether you're a magazine, a soft drink, a car, or a computer company, you can't spend too much time leveraging your heritage in today's market," O'Malley says. "It matters, but you've got to interpret it in a modern way."