Just shoot me now.

That might be a normal journalist’s reaction to news that the subject of a mega-profile for a magazine cover story has declined to be interviewed for the piece. But in the mid-1960s Gay Talese was anything but a “normal journalist.” When Frank Sinatra offered not so much as a “Buzz off!” in person, Talese kept reporting in his meticulous way as the persistent eyewitness, eventually writing a Sinatra story that caused a national sensation and pioneered a narrative style of nonfiction later dubbed the New Journalism.

Frank Sinatra Has A Cold” appeared in Esquire in April 1966. In October 2003, for the magazine’s 70th anniversary, editors pronounced the Talese piece the best story Esquire had ever published. And of course the story appeared in Talese’s classic story collection “Fame and Obscurity,” which New York University’s journalism department named No. 43 among the 20th century’s top 100 works of American journalism.

Why’s it so good? I could point to any of the usual signposts for superb literary nonfiction – scenes, dialogue, characters, interior monologues, the beginning, the ending, digressions and a structure that suggests a larger meaning. The 15,000-word story is as finely crafted as Sinatra’s (and Talese’s) custom-tailored suits. I prefer today to praise the humble but honest work that should come with any journalism, new or old: reporting.

Talese’s curiosity fuels his research in such an expansive way that we learn the paradoxical tale of Sinatra the arrogant, tempestuous celebrity and Sinatra the lonesome, sentimental man, a part of whom, Talese writes, “no matter where he is, is never there.” It required prodigious reporting to write with such confidence a crystalline description that serves as the essence of this piece.

The mastery begins with Talese reporting on Sinatra’s origins and family life. Biographical details abounded. Sinatra had been the subject of published articles for decades. How could Talese bring something fresh to the task? First, he was Italian-American. He understood Sinatra’s culture from an insider’s point of view. He knew the relevant layers of cultural experience and where to mine the telling details, the “remarkable juxtaposition of the pious and the worldly” − the photographs of Pope John and Ava Gardner, the statues of saints and holy water, and a chair signed by Sammy Davis Jr., for instance, all in Sinatra’s parents’ home. Best of all, he landed an interview with Dolly, Sinatra’s mother, “a large and very ambitious woman,” an agile player in Hoboken’s Democratic political machine and not the sort of Italian mother who could be appeased “merely by a child’s obedience and good appetite.”

Without saying it outright, Talese underscores the region’s historical political tensions when he writes:

In later years Dolly Sinatra, possessing a round red face and blue eyes, was often mistaken for being Irish, and surprised many at the speed with which she swung her heavy handbag at anyone uttering “Wop.”

She threw a shoe at her son when she learned he wished to become a singer. “Later, finding she could not talk him out of it – ‘he takes after me’ – she encouraged his singing,” Talese writes. Such reporting on family history forms the foundation that allows us to savor revelations that Talese deftly introduces through scenes in Las Vegas, a New York saloon, a poolroom, a recording studio and a movie lot. We have context for our character because Talese has shown us the origins of Sinatra’s world.

Now pay attention to the minor characters. Talese assigns them illuminating roles to help us understand Sinatra. Here is how Talese deals with a dreaded story obstacle: the press agent. In this case, the anxious flack is Jim Mahoney, and we learn Mahoney has plenty of reason to worry:

Still, Sinatra seems ever present, and if Mahoney did not have legitimate worries about Sinatra, as he did today, he could invent them – and, as worry aids, he surrounds himself with little mementos of moments in the past when he did worry. In his shaving kit there is a two-year-old box of sleeping tablets dispensed by a Reno druggist – the date on the bottle marks the kidnapping of Frank Sinatra Jr. There is on a table in Mahoney’s office a mounted wood reproduction of Frank Sinatra’s ransom note written on the aforementioned occasion. One of Mahoney’s mannerisms, when he is sitting at his desk worrying, is to tinker with the tiny toy train he keeps in front of him – the train is a souvenir from the Sinatra film, Von Ryan’s Express; it is to men who are close to Sinatra what the PT-109 tie clasps are to men who were close to Kennedy – and Mahoney then proceeds to roll the little train back and forth on the six inches of track; back and forth, back and forth, click-clack-click-clack. It is his Queeg-thing.

We are wringing our hands by the time we finish reading about this poor guy and his woes. Yet by developing Mahoney as a character, even only slightly, we somehow see Sinatra more clearly.

And in the following passage Talese relays some old news, but settling his unerring eye on a nameless, minor character reveals more than the standard tattler fare:

He also wore, as everybody seemed to know, a remarkably convincing black hairpiece, one of sixty that he owns, most of them under the care of an inconspicuous little grey-haired lady who, holding his hair in a tiny satchel, follows him around whenever he performs. She earns $400 a week.

(Talese anticipated our curiosity about that paycheck. Today, her salary would be roughly $2,800 − not bad for toting hair.)

These minor characters surround Sinatra as agents who serve, protect and sometimes fear him. Examine each one, and you will come away impressed by the intense reporting that Talese had do to unearth their stories. He doesn’t overwhelm us with their presence; each one’s appearance, carefully placed, deepens our understanding of Sinatra he approaches his 50th birthday.

Talese’s gift for observing detail gives us immediate, vivid imagery that put us right there in the room with Sinatra. The tension is palpable as Talese recounts the poolroom scene in which one of “coolest” in the bar, writer Harlan Ellison, drew Sinatra’s ire for wearing Game Warden boots, “for which he had recently paid $60.” Talese has Sinatra gazing at those boots, turning away, focusing on them again and then firing questions at Ellison about the provenance of the boots. “I don’t like the way you’re dressed,” he tells Ellison. Throughout the slowly evolving, hostile scene, Talese conveys the precise action in the background −  from the man who was bent low with his cue stick and then froze, to the “hard tap of Sinatra’s shoes” as the singer made his way with a “slow, arrogant swagger” from his stool to face off with Ellison. In simply writing what he saw and heard, Talese built scenes around straight action, which builds drama, emotion. In one scene, Talese conveys the “kind of airy aphrodisiac” of Sinatra’s music through young couples moving languidly on a dance floor, holding each other close.

By giving us a portrait of Sinatra, Talese also gives us a portrait of L.A., “a lovely city of sun and sex, a Spanish discovery of Mexican misery, a star land of little men and little women sliding in and out of convertibles in tense tight pants.”

Without such relentless reporting none of this would have been possible. Who cares if the subject won’t cooperate? In the right hands, there’s always a story.

Maria Henson (@mariahenson), a 1994 Nieman Fellow, won the Pulitzer Prize for editorial writing in 1992 and edited the Sacramento Bee’s 2005 Pulitzer Prize-winning editorial series about Hetch Hetchy. She teaches journalism and serves as vice president and editor-at-large at Wake Forest University, which last month screened “Editor Uncut,” a documentary in production about WFU alumnus and Esquire editor Harold T.P. Hayes. Created by Hayes’ son, Tom, the film includes an interview with Gay Talese about “Frank Sinatra Has a Cold.

For more from our collaboration with Longreads and Alexis Madrigal, see the previous posts in the series. And stay tuned for a new shot of inspiration and insight every week.

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