In November of 1965, the journalistic fates brought Gay Talese and Frank Sinatra together in Beverly Hills and Las Vegas, Manhattan and Hollywood. Well, sort of. They were two guys from New Jersey, both of them Italian-American, given to Continental tailoring, unstoppable ambition, and unrelenting perfectionism in their chosen crafts. Talese, the writer, was traveling on assignment for Esquire, the It Magazine of the decade. Edited by Harold Hayes, Esquire made the so-called New Journalism famous—or infamous, depending on your point of view. (Talese disliked the term, promulgated by his friend Tom Wolfe.) Sinatra, the singer, was the 20th century’s reigning entertainment icon, the Rat Pack ringleader, a tuxedoed man’s man in the shaggy era of the Beatles and the Byrds.

Just One Hitch

Hayes had commissioned Talese to write a cover profile of the singer. It was meant to be a celebration of all things Sinatra as the living legend approached the golden, if worrisome, age of 50. (His birthday was December 12.) Amid an outpouring of projects that would make younger pop stars blush (two network-television specials, two albums, a movie), the Esquire cover would top it all off. There was just one hitch: Sinatra had a cold.

The cover by Ed Sorel of the April 1966 issue of Esquire and the opening page of Gay Talese’s story.

Fifty-four years later, the resulting piece, “Frank Sinatra Has a Cold,” which ran in the April 1966 issue of Esquire, remains one of the most incisive portraits of Sinatra ever created and probably the most renowned, studied, and picked-apart celebrity profile in American nonfiction. Talese turned Sinatra’s post-nasal drip into a metaphor for the singer’s outsize impact upon the entire entertainment industry. The seasonal ailment, as Talese told it, also became Sinatra’s opportunity to renege on an agreement to sit for an interview: a profile of Sinatra, with no Sinatra.

Sinatra with Ed Sullivan, Eden Roc, Miami, 1964.

Talese went into gumshoe mode. The 33-year-old writer observed his quarry at the Daisy in Beverly Hills, a members-only redoubt of California cool where Sinatra got into a scuffle with the science-fiction screenwriter and author Harlan Ellison over a pair of trendy boots; at a jam-packed Jilly’s, on West 52nd Street, in Manhattan, where Sinatra held court and even the New York Giants’ halfback Frank Gifford couldn’t get through the crowd to him (“only seven yards in three tries”); at the Ali-Patterson heavyweight-title bout in Las Vegas, on the second anniversary of the Kennedy assassination (Patterson, profiled by Talese the previous year, was TKO’d in the 12th); at the Sahara and the Sands, where Sinatra partied all night with his Rat Pack pals, including Dean Martin, who emptied a bottle of whiskey on his own head; at NBC’s Burbank studios, where the congested singer failed to get through a taping of the TV special Frank Sinatra: A Man and His Music (“Boy, do I need a drink”); on the Paramount lot, where Sinatra shot a racy scene with the Italian siren Virna Lisi for Assault on a Queen and made frequent, inscrutable references to his “bird”; and inside United Recording Studios in L.A., where Sinatra’s voice, back in form, caused all jaws to drop, including Talese’s. Here, at last, was Sinatra in his glory, beyond the reach of fame or age or clogged sinuses: an American artist.

Talese turned Sinatra’s post-nasal drip into a metaphor for the singer’s outsize impact upon the entire entertainment industry.

Unable to score the customary interview, Talese, by his own estimate, spoke with more than 100 people in Sinatra’s orbit, gathering insight into the singer’s retinue of employees and attendants (including the “superbly tailored” press agent, Jim Mahoney, and the “little grey-haired lady” who allegedly earned $400 a week carrying Sinatra’s hairpieces around in a satchel), his vast holdings (including a missile-parts firm), his famous temper (you were not, under any circumstances, to present Mr. Sinatra with a hot dog dressed with ketchup), and his famous generosity (an expansive Christmas-gift list, covering friends’ hospital bills).

Talese in his Manhattan home, 1969.

Talese viewed Sinatra as not only a sublime jazz singer, maestro of media attention, and movie star, but as a singular midcentury figure who personified two distinct, and opposing, masculine types: the jet-age swinger and the ancient Sicilian padrone—the village patriarch who commanded respect, settled scores, solved problems, righted wrongs. And yet the guy could be brought low by the most quotidian and human of infirmities. “Sinatra with a cold,” Talese wrote, “is Picasso without paint, Ferrari without fuel.”

The Rosetta Stone

Today, “Frank Sinatra Has a Cold” is considered a high-water mark of the New Journalism, a Hall of Fame feat of immersive reporting on a non-participating subject. It’s the ultimate instance of a reporter turning his biggest nightmare—known in the trade as a “write-around”—into storytelling gold. “I gained more by watching him, overhearing him, and watching the reactions of those around him,” Talese once said, “than if I had actually been able to sit down and talk to him.”

Dean Martin, Sammy Davis Jr., and Sinatra, backstage at Carnegie Hall, following a benefit honoring Martin Luther King Jr.

It is a Rosetta stone of profile writing, along with, say, Joseph Mitchell’s “Professor Sea Gull,” a 1942 New Yorker profile of Joseph Gould, the indigent Greenwich Village bohemian allegedly scribbling away at a nine-million-word Oral History of Our Time, and Lillian Ross’s 1950 profile in the same magazine of a bibulous, malarkey-talking, and uniquely charismatic Ernest Hemingway, “How Do You Like It Now, Gentlemen?”

It’s the ultimate instance of a reporter turning his biggest nightmare—known in the trade as a “write-around”—into storytelling gold.

You pore over Talese’s story and wonder: How did he do it? Where was he standing when the altercation at the Daisy blew up? How did he ever end up talking to the singer’s mother, the formidable Dolly Sinatra of Fort Lee, New Jersey? How did he create the cinematic closing scene of Sinatra in his Ghia at a stoplight, smiling at a girl on the sidewalk? (“It looks like him, but is it?”) In recent years, some of these mysteries have been cleared up by Talese himself here and there, as in the annotated version of the piece posted online by the Nieman Foundation at Harvard in 2013, and in a Paris Review Art of Nonfiction interview in 2009.

If anything, Talese’s elucidations—showing the stitching underneath the fabric, as it were—have only added to the story’s legend. Its renown has also been nourished by the drama of its creation: the high-pressure assignment, the young writer, the evasive superstar. Ever the tailor’s son, Talese made his outlines on shirt boards. On the multicolored one he created for “Frank Sinatra Has a Cold,” Talese recorded hopeful anticipation upon arrival in Los Angeles to begin the reporting: “Article would be an opportunity to ‘swing’—have fun,” he jotted, amid swirling arrows and cascading paragraph symbols, a D.I.Y. riot of black, brown, blue, green, red, orange, and yellow ink that feels almost Blakean.

Instead, Talese experienced dread, mistrust, self-recrimination, fear, and paranoia—with room service. (He took careful note of the Beverly Wilshire’s “sexy chambermaids.”) “Mahoney was saying be careful—don’t talk to him.” No interview! What a headache! Didn’t Harold Hayes know that Talese liked profiling the little guys, the unknowns, the losers, the has-beens? Sinatra! Would this assignment ever amount to anything? Was he being typecast as an Italian-American? “FUCK HAYES,” Talese wrote, all caps. He was reporting his own writerly meltdown in addition to an Esquire cover story.

Sinatra with his parents, Dolly and Martin, circa 1965.

Yet, for all the turmoil, modern readers of “Frank Sinatra Has a Cold”—including creative-writing majors, M.F.A. nonfiction candidates, and J-schoolers—discover a window onto a colorful, glamorous heyday of print journalism. Talese was able to spend as many as 10 weeks to report and write. He accumulated expenses of nearly $5,000 (the equivalent of about $41,000 today) and filed a 50-page draft derived from what he described as a “two-hundred page chronicle”—all those shirt-board outlines, interview notes, and general observations, a veritable kitchen midden of reporting that Talese ran through his typewriter.

This document still ostensibly resides in Talese’s writing “bunker” beneath his Upper East Side town house, where he has lived and worked for more than 50 years, creating whopping best-sellers such as Thy Neighbor’s Wife and Unto the Sons, presiding over his extensive archives, and occasionally weathering Twitterstorms, all while being married to the influential publisher Nan A. Talese and raising two daughters.

By the late 1980s, Talese was already bemoaning the lapsed glory of magazine journalism, which he argued had been compromised into mediocrity by sleepy, tape-recorded interviews and budget cuts: “Fast-food computerized bottom-line impersonalized workmanship.” Thirty years further down the line, in an age when magazines are being turned into Instagram accounts and newsstands have vanished, the investment in storytelling represented by “Frank Sinatra Has a Cold” seems downright gaudy. It’s a jarring artifact from a time when journalism aspired to art and ad-glutted magazines—Esquire, Time, Life, The New Yorker, The Saturday Evening Post—could make or break Hollywood movies, presidential campaigns, even global entertainment icons with head colds.

Well, here we are: another end-times threnody on the lost splendor of legacy media. There is still great magazine writing out there, with new voices emerging every week. Read them. They are the Talese, Wolfe, Didion, Sontag, Baldwin, and Kael of now. Yet don’t forget that on a winter weekend in the exasperating 21st century, with something more serious than rhinovirus going around, you might want to go read or re-read “Frank Sinatra Has a Cold”—the story of the 20th century’s greatest entertainer and the reporter he tried to elude but who captured him for all time.

Mark Rozzo is an Editor at Large for Air Mail