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ESQUIRE IN THE SIXTIES THROUGH THE EYES OF HAROLD HAYES' SON 

By Roxana Vosough





“Esquire in the Sixties” — if you’re a magazine editor, you say those words in a hushed, reverential voice. That magazine in that era represents the best it has ever been for us, the apex of the craft. Or so the legend goes.” – Hugo Lindgren, New York Times Magazine Editor-in -Chief







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​​​​​​​​​​​​Smiling Through the Apocalypse OFFICIAL Trailer





It was during the sixties that Esquire magazine, now known for its insight into men’s fashion and annual “Sexiest Woman Alive”, revolutionized and revitalized the publishing industry.  Under the direction of Editor-in-Chief, Harold Hayes, Esquire fostered journalists whose writing and points of view were experimental and bold, popularizing the unconventional writing style known as New Journalism, and took on divisive topics like civil rights, the anti-war movement, drugs, and even the women’s movement.  With Hayes at the helm, Esquire not only captured the zeitgeist of the time, but was also able to breath new life into the publishing industry, cementing their place in American journalism.  The re-incarnation of a new era began with his reign as Editor-in-Chief of Esquire in the sixties.







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​​​​​​​​​​​​August 1966 Esquire Cover | Image Courtesy of Tom Hayes





In an era where many magazines were following the “dull, mannered strictures of the 50s…provocation, on many levels, was exactly what Hayes sought...he had pushed to make every column inch of the magazine sing with a brash authority that made news and upset the powers that be”, explains Frank DiGiacomo, in his eight page article on Hayes’ legacy, in a Vanity Fair piece entitled The Esquire Decade.



Filmmaker, and son of the late Harold Hayes, Tom Hayes, was so inspired by DiGiacomo’s article and his father’s legacy that he set out on the daunting task to create a film documenting Hayes’ achievements at Esquire. He started by conducting interviews with some of today’s most famous screenwriters, publishers, and writers including Hugh Hefner, Nora Ephron, Guy Talese, and Tom Wolfe. The feature-length film, entitled Smiling Through the Apocalypse: Esquire in the Sixties, captures the essence and powerful change that Hayes brought to the magazine industry.



“I felt that it was the best thing I ever did”, says Tom about making the film.

“The impact of his death crept forward in weird ways. It took me 6 months before I actually cried…one afternoon I just balled”.

Hayes, who passed away in 1989, certainly left his mark, as evidenced by the many tributes from acclaimed individuals, such as the then Vanity Fair Editor, Tina Brown, who made a very powerful tribute, says Tom. However it was not until, 18 years later in 2007 when DiGiacomo’s article re-struck a chord in Tom and he decided to embark on the challenging journey of creating a documentary about the influence and legacy of his late father.



“In 2009”, says Tom, “I started chasing down all these people to kind of explain the je ne sais quoi that my father had”, and the process of making the film began. Tom had extensive experience in German television production, which gave him the tools to begin the project.  However Tom’s experience in television production did not prepare him for the spontaneity and unpredictable nature of documentary filmmaking. “I really didn’t know how I was going to do this film. With doc filmmaking, you never know how it is going to come out”, explains Tom reluctantly, “it’s everything I never knew and more”.  His first interview was with acclaimed photojournalist, Robert Frank, who rarely does interviews, was a learning curve. “When I ran out of questions, he picked up the interview and started asking me questions. I started feeling inadequate” explains Tom. Interviews could be “slightly intimidating, you can only hope for the best”.



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​​​​​​​​​​​​The Esquire Staff in the sixties | Image Courtesy of Tom Hayes





When entering the Playboy mansion to interview the former Esquire employee, also known as Hugh Hefner, Tom recalls, “He’s a pro, we got there and lights were already set up. He is an incredible documentarian. He has a collection of every documentary that has been done of him”. While Tom was documenting Hefner, Hefner had someone documenting and filming them.  Tom cheerfully gloats that Hefner proclaimed in the film,

“one of the things that was fascinating for me is that Esquire was not allowed in my home, it was an adult magazine”.



In the end, “you want to distill that experience in some way that is going to be linear” explains Tom.  In his eyes “my father was an enabler, he enabled people to do things”, and as a result people had a tendency to focus more on themselves and their own achievements rather than Hayes’ legacy. However all this “storytelling”, explains Tom, was what comprised Hayes’ era, and his affect on his staff, as explicated in his famous memo (below).









 The acclaimed journalist, screenwriter, director, and author Nora Ephron (You’ve Got Mail, Sleepless in Seattle, Julie & Julia), was also a particularly notable interview, according to Tom. “We were invited to her Upper West Side townhome, during their lunch break. We were told to wait for a text, to come in and do the interview…she said the most glowing stuff about him…it was like a Valentine’s Day card”. The late Ephron, who passed away in 2012, is quoted as saying “he made you feel so incredibly safe at Esquire. He was all about protecting the artist’s voice. He should’ve become more famous”.



Surrounded with what Tom calls “a great batch of subjects” who were all “great and articulate minds, [who could] speak and tell stories well”, allows for an eloquent ballad explicating Hayes’ great affect on Esquire.



“He was the real Don Draper”

says Tom, referring to the fictional Mad Men character portrayed by the charismatic Jon Hamm. The film, Smiling through the Apocalypse: Esquire in the Sixties is “more about my interest to know his genius, than how human he was” explains Tom. It was Tom’s firm belief that “parents should never show their weaknesses”. Thus the film was strict in its narration, recorded by Tom, focusing on Harold P. Hayes the editor versus Hayes the father and husband. Tom also had the gracious production assistance of his sister and stepmother, who he says both “knew him, [Harold], in a different way, rounding out areas that were foggy for me”.



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 Overall, the film took nearly three years to complete, largely due to “waiting for people to come and talk to me, some people took two years. People who you thought would be first, were often last”, says Tom.  Despite setbacks such as these, it was Tom’s drive and commitment, characteristics he may have inherited from his esteemed father that ensured the completion and success of his documentary film project.



Smiling Through the Apocalypse: Esquire in the Sixties takes you on the fearless journey of a man whose hard work, dedication, and tenacity revitalized the magazine industry. It serves as a brilliant reminder of where we once were in publishing and the incredible affect it can have on society, through the editorial direction of Harold Hayes, a man who was given the freedom to express his vision and direct the voices of some of the most notable writers of his generation. This film should not be missed, especially by those interested in the publishing world and its immense potential for intellectual sophistication







The film premiered at the International Film Festival in Palm Springs. It has since been released for a private screening on Broadway this past week for the cast, and will release on the West Coast, at the Newport Beach Film Festival in April.

Roxana Vosough, is the Founder & Publisher of Mode-Moderne Journal



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