Autumn 1933: the first issue of Esquire Magazine. Photography: Hearst International


IT IS SENSIBLE for any magazine to have a clear idea of who it thinks its ideal reader is. When Esquire was launched in the United States in October 1933, the magazine’s founders went so far as to commission an illustration. Esky, as he was christened, was the creation of the pioneering Black cartoonist E. Simms Campbell, who’d learned his craft sketching the passengers on the trains whose dining car tables he’d once cleared. Esky was an affectionate caricature of a pre-World War II urban dandy, both stylish (the luxuriant silver moustache, swish black homburg) and wryly inquisitive (the bulging blue eyes beneath sardonically arched eyebrows). Some representations of Esky reinforced the point by adding a rolled-up copy of Esquire, tucked beneath one sleeve of a smartly cut overcoat.

But Esky had clearly led a life enjoyed by few Americans of this period. It was only four years since the Wall Street Crash had destroyed the nation’s economy, and though recently inaugurated new President, Franklin D. Roosevelt, had launched the eventually transformative measures known as the New Deal, nearly a quarter of the workforce remained unemployed. An unabashedly aspirational magazine like Esquire was a big bet on America’s optimism, and capacity to reinvent itself.

This wager was placed by Chicago publisher David Smart, New York businessman Henry L. Jackson—who also had a background in journalism—and Michigan editor Arnold Gingrich. They toyed with a few different mastheads: their new magazine might have been Trim, Beau or Stag, until the eye of Gingrich’s secretary was caught by a letter to her boss. It was addressed to Arnold Gingrich, Esq.

Esquire began life as a quarterly. The first issue, priced at 50 cents and dated Autumn 1933, promised “Fiction, Sports, Humour, Clothes, Art, Cartoons”. The cover image, of a scarlet seaplane recently arrived in some sun-splashed tropical bay, was framed in an olive sidebar with bold black type splashing a remarkable cast of contributors for any edition of any publication, never mind a debut: Dashiell Hammett, Douglas Fairbanks Jr., John Dos Passos, Morley Callaghan. Top billing, however, went to a writer who would define the Esquire vision, and as a partial consequence, 20th century American journalism: Ernest Hemingway.

Gingrich had lined Hemingway up from a way off. Hemingway, still in his mid-30s, was already colossally famous, with The Sun Also Rises and A Farewell To Arms behind him. Gingrich accosted him in a New York bookshop, then sent him the kind of letter that every writer dreams of receiving.

Frank Sinatra Esquire
April 1966: Frank Sinatra. Photography: Hearst International.

“Esquire,” wrote Gingrich, “will try to be to the American male what Vogue is to the female. It aims to have ample hair on its chest, to say nothing of adequate cojones. Just short of splitting a bowel, I’ll try anything to sell you the idea of being in that first issue. Something about fishing in Florida. Or about hunting. Or about anything you like. And—I promise—no editing whatever. You write and I print—no monkey business en route to the printers.” In the first 33 issues of Esquire, Hemingway’s incalculably influential byline appeared 28 times.

Esquire was an instant hit. By 1937, it was making enough of a profit to justify a listing on the New York stock exchange (and by 1938, 12 of its executives had been indicted by the Securities and Exchange Commission for cooking the share price, but nobody’s perfect). It had the reach, the money and the cachet to attract more or less anybody it liked. A partial list of contributors Esquire acquired through the 1940s, ’50s and ’60s includes J.D. Salinger, Truman Capote, Norman Mailer, Diane Arbus, Tom Wolfe, F. Scott Fitzgerald, Thomas Pynchon, Terry Southern, Joan Didion, James Baldwin and Gay Talese. Talese’s 1966 profile of Frank Sinatra is frequently and correctly admired as a benchmark character study, and for having one of the most glorious opening lines in journalism: “Frank Sinatra, holding a glass of bourbon in one hand and a cigarette in the other, stood in a dark corner of the bar between two attractive but fading blondes who sat waiting for him to say something.”


BY THE TIME Talese’s piece “Frank Sinatra Has A Cold” ran, it was instantly recognisable as an example of what had become known as the New Journalism—journalism, that is, that aspired to the qualities of literature, which sought to present readers with a great deal more than just the facts. Many writers think they can write it, and many publications think they can publish it, and both are usually wrong, but Esquire’s roster, and Esquire’s resources, were equal to its requirements (if you want to make a modern freelancer weep, remind them what Esquire was paying its writers half a century ago).

Esquire’s commitment to literary longform journalism arguably peaked with the publication, also in 1966, of conflict correspondent John Sack’s epic “M”: fully 33,000 words, and not one wasted, chronicling one US Army infantry company’s journey from basic training at Fort Dix to combat in Vietnam. “M” was also an illustration of Esquire’s acute understanding of how a magazine cover could reach from a news-stand straight for the throat of the browsing reader. It was probably the simplest cover for which Esquire’s legendary art director George Lois was ever responsible, but it was a masterpiece: a plain black cover emblazoned with white letters spelling out the aghast exclamation “Oh my God—we hit a little girl”. It summed up not merely a gripping story, but a misbegotten war.

Muhammed Ali Esquire
April 1968: Muhammad Ali. Photography: Hearst International.


The covers dating from Lois’s stint at Esquire, from 1962 to 1973, are arguably as great an artistic representation of the period as anybody assembled—this assessment very much including one cover star, Andy Warhol, who Lois depicted drowning in a can of Campbell’s tomato soup to illustrate a May 1969 story on the decline of the American avant-garde. This was a signature Lois cover in that it negotiated a delicate balance—in this instance, waspish yet affectionate. Lois could also do solemnity without being mawkish—Esquire’s 35th anniversary edition, in October 1968, placed the recently assassinated John F. Kennedy, Robert F. Kennedy and Martin Luther King Jr. besuited among the tombstones of Arlington National Cemetery, as if attending their own wakes. He could do confrontational but graceful, in April 1968 imagining Muhammad Ali as Saint Sebastian after the boxer had been stripped of his titles for refusing to submit to the Vietnam draft. He could do alluring without (quite) leering, in February 1964 arraying a beauty pageant of uniformed air stewardesses.

And he could create profitable, purposeful uproar. In December 1963, Esquire’s Christmas issue bore an image of world heavyweight champion Sonny Liston, wearing a doleful expression and a Santa Claus costume. Lois later recalled that he showed the cover to the up-and-coming boxer who would, a couple of months later, take Liston’s title from him. “That,” chuckled Cassius Clay, later Muhammad Ali, “is the last Black motherfucker America wants to see coming down their chimney.” So it proved. At a time of roiling racial tensions, a hefty cohort of white America regarded the picture, taken at Lois’ direction by photographer Carl Fischer, as near- blasphemous. Esquire’s phones rang red with complaints, subscriptions were cancelled, advertising pulled—US$750,000 worth, from the year’s most financially important edition.

Esquire Andy Warhol
May 1969: Andy Warhol. Photography: Hearst International.

WHEN IT CAME TO APPROACHING the subject of arguably greatest interest to its largely male readership—i.e., women—Esquire tried to keep it, by and large, classy. It preferred not to see the likes of Playboy—founded by a former Esquire copywriter called Hugh Hefner—as a peer, or a competitor: Esquire took pride in being a men’s magazine whose readers actually did buy it for the articles.

This is not to say Esquire ever shied from printing pictures of not overclothed women, though especially early on Esquire strove to do this in a more artistic fashion, via the pin-up girls sketched by George Petty and Alberto Vargas. Paintings inspired by their works became popular nosecone decorations of World War II combat aircraft, most famously Petty’s “Memphis Belle”, which adorned the legendary B-17 bomber of the same name. These were not universally appreciated, however. In 1943, the Postmaster General brought charges against Esquire on the basis that it was using the US Postal Service to distribute these “lewd images”; in 1946, the US Supreme Court decided that the Memphis Belle and her compadres were protected by the First Amendment.

And it would be a reach to suggest that Esquire has never overstepped the boundaries of gentlemanly decorum, especially when besieged in the late 1990s and early 2000s by a raffish new generation of print publications (Maxim, FHM, et al). In 2004, an annual Sexiest Woman Alive feature was instituted (first honouree, Angelina Jolie). After 2015, and a decade of richly merited criticism of the queasily lubricious tone of these profiles, it was abandoned (last honouree, Emilia Clarke).

March 1991: Bridget Bardot. Photography: Hearst International


The run of Sexiest Woman Alive coincided almost exactly with a hiatus of Esquire’s Dubious Achievement Awards, which ran initially from 1962 to 2008. That the two institutions only briefly overlapped was probably just as well, lest Esquire find itself in the awkward position of eventually having to present trophies to itself. The DAAs were revived in 2016, in time to declare that the Dubious Man of The Year was the new president-elect, Donald Trump—who had previously been, in August 2004, Esquire’s cover star, strung with glittering bling, photographed in mid-bellow, trailing an interview headlined “How I’d Run The Country (Better.)” The possibility that it gave him ideas cannot be discounted.

Bill Clinton Esquire
December 2000: Bill Clinton. Photography: Hearst International.


THE 21ST CENTURY has not been widely considered a golden age of magazine journalism. The internet demolished the business model that had allowed a magazine like Esquire to flourish. Readers went online, and became accustomed to free media. Advertisers followed them, and magazine budgets dwindled accordingly. A hyperactively whirling news cycle further discouraged ruminative longform reporting.

Despite these daunting challenges, Esquire continued to find ways to be Esquire. David Granger, editor-in-chief of US Esquire from 1997 to 2016, revived the title for the modern era substantially by returning to its founding values. He brought with him from GQ, where’d he’d been executive editor, such talents as Tom Junod; he hired David Sedaris, Chris Jones and Charles Pierce, among many others.

Also on Granger’s watch, Esquire re-embraced its literary tradition with the 2007 launch of the Napkin Project: in a nod to the origins of at least some of Hemingway’s works, Esquire sent cocktail napkins to 250 writers, inviting them to fill the space as they saw fit. For the better-known names—Rick Moody, Jonathan Ames, Z.Z. Packer, among others—an engaging whimsical exercise: for the up-and-comers, an opportunity, the literary equivalent of a comedy venue’s open-mic slot. Esquire revived the Napkin Project in 2023, once again demonstrating the multitudes that a great writer can cram into a small space.

Philip Seymour Hoffman Esquire
March 2013: Philip Seymour Hoffman. Photography: Hearst International.

As the interests of its readers have evolved, so too has Esquire’s coverage. One of the greatest cultural shifts of the last five years has been the attention men pay to fashion and celebrity, and indeed, Esquire’s most recent photo shoots have featured some of the most daring looks to come from the runways—Kid Cudi’s August 2022 cover story, which features an image of the American rapper wearing nothing but a monogrammed Dior sock on his family jewels, is nothing if not unforgettable.

Esquire also launched the Big Black Book, a biannual manual offering instruction on how the modern man might conduct himself in the style Esquire had long encouraged.

Summer 2019: Brad Pitt, Quentin Tarantino and Leonardo DiCaprio. Photography: Hearst International


And Esquire’s history has created a global reputation, with 27 global editions. Australia becomes the latest boulevard down which Esky will stroll, and he should feel right at home. He has, after all, an Australian name.

This story was published in the October/November 2023 issue of Esquire Australia. Subscribe here.

Read Esquire Australia’s cover stories:

This is not a Nick Kyrgios redemption story

The extraordinary world-building of Genesis Owusu

The rebuilding of Ben Simmons