Hugh Hefner’s Legacy as Told Through National Portrait Gallery Artifacts

Three objects explore the complicated and controversial life of the late founder of the Playboy empire

Hugh Hefner
This 1966 portrait of Hugh Hefner will go on display today in the Smithsonian National Portrait Gallery National Portrait Gallery

In the collections of the Smithsonian's National Portrait Gallery, there's 1966 photograph of Hugh Hefner. In it, the man who built the Playboy empire leans forward confidently on a chair. He's perfectly coiffed in a suit, and a pipe rests on the corner of his lips. The shot captures a moment where he's just turning around from his work, except he's barefoot. Lounging around him are four women in evening clothes, also barefoot. Three of them are chatting, one looks directly at the camera.

The photograph of Hefner, who died Wednesday at the age of 91, was taken in the original Chicago Playboy Mansion by photojournalist Art Shay as part of a Time magazine cover story on Hefner, according to Ann Shumard, senior curator of photographs at the National Portrait Gallery. In an email interview with, Shumard writes that Shay said Hefner had "called the ladies in, and they just naturally draped themselves around.”

"The picture reflects Hefner’s carefully cultivated image as the freewheeling man-about-town who surrounds himself with a coterie of alluring young women," Shumard writes. "The National Portrait Gallery acquired this photograph because it captures Hugh Hefner at the peak of his influence, when Playboy magazine was described as mid-20th century America’s 'most successful magazine publishing venture.'"​

At first blush Hefner, a married man who'd worked previously for a children's magazine, seemed an unlikely figure to found a controversial and radical empire of sexuality and provocation. But the Playboy founder, who grew up in a repressed Midwestern household, wanted to take an aim at Puritan American values, as Laura Mansnerus reports in her obituary on Hefner in the New York Times. That's exactly what he did in 1953, when Hefner published the first issue of Playboy, a magazine targeted at the interests of the "modern man" who liked sex, but also intellectual pursuits and quality alcohol. A look back at the first issue, which was reprinted in 2014, reads like a time capsule into the "Mad Men" era, with an article about "desk designs for the modern office" alongside a nude calender photo of Marilyn Monroe (taken before her star ballooned, when she was desparate for money).

But as much as Hefner embodied "Mad Men"-era style, he continually pushed to reform it. Another photo in the collections of the National Portrait Gallery shows a different side of Hefner's legacy. There, Hefner stands with Civil Rights leader Jesse Jackson in 1972 at a fundraiser for the latter's Rainbow PUSH coalition. Hefner was a longtime activist for the Civil Rights movement, and used Playboy as a vehicle to feature black writers and entertainers. Before Roots, Alex Haley published the magazine's first interview with Jazz icon Miles Davis, and later his explosive interview in Playboy with Malcolm X led to The Autobiography of Malcolm X.

The pages of Playboy were political in many ways, Derek Hawkins writes for the Washington Post. For example, Hefner was an early promoter of LGBTQ rights and published articles on the AIDS crisis and transgender people long before mainstream publications. But Hefner's most remembered for taking aim at sexual politics. A major force in the burgeoning "sexual revolution" he opened up once taboo subjects to wider discourse. As Amber Batura writes for the New York Times, Hefner used his publication to disseminate the "Playboy Philosophy" that sought acceptance for birth control among other topics. 

Though he once proclaimed that he was a "feminist before there was such a thing as feminism," Hefner's legacy will always be tied to controversy when it comes to his treatment of women. In the 1960s, Gloria Steinem went undercover as a Playboy Club waitress to reveal how the club exploited and demeaned its female workers, and over the years, Hefner has weathered a storm of critics who said he'd exploited and objectified young women. A 2015 Buzzfeed News article by Kate Aurthur, for instance, documents allegations by a former Playboy Bunny of the sexually abusive environment inside Hefner's California Playboy Mansion.

The National Portrait Gallery is also home to Marisol Escobar's penetrating sculpture of Hugh Hefner, which may be the most fitting way to remember the larger-than-life figure, who leaves beind an open debate on his legacy.  

In the distorted wooden sculpture, she gives Hefner two pipes, one in his mouth and another in his hand. "It is an awkward image, sharing nothing of the glossy airbrushed world of Playboy," according to the description

Later, when speaking about the decision to give the statue two pipes, Escobar said: “Well, Hugh Hefner has too much of everything.”

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