On Sunday, April 9, Hugh M. Hefner will celebrate his 91st birthday. For those interested in the math, that means Hef has been the original Mr. Playboy for more than two-thirds of his life, having founded the magazine in December 1953 at the age of only 27. Soon after, Hef created a global empire that has included nightclubs, a music fest, two residences, multiple TV shows, one famous Bunny suit and a Rabbit Head logo that represents the good life across the world. All of this had a hand in revolutionizing the way Americans think about sex and, in tandem with historic moments like the publication of The Kinsey Reports, the development of the birth control pill and post-war economic independence for women, Hef helped ignite a sexual revolution in the 1950s and 1960s.

Today, Playboy is as synonymous with the word sex as it is with Hef himself. But more than just pushing boundaries—and removing buttons—in the magazine’s famed pictorials, Hef has involved himself in sophisticated conversations about sex at every level—from our right to privacy to our right to explore our most carnal desires without shame. At every turn, Hef has done it without sacrificing humor, joy and entertainment. As he wrote in Playboy’s debut issue, “We don’t expect to solve any world problems or prove any ggreat moral turths. If we are able to give the American male a few extra laughs and a little diversion from the anxieties of the Atomic Age, we’ll feel we’ve justified our existence.”

To say Hef has done more than that is an understatement. And so, as he celebrates turning 91 years old, we thought it right to round up 10 of the biggest moments wherein Hef changed how we considered sex. From creating a new fantasy in the form of the “girl next door” to the thrill of finding your dad’s Playboys to challenging the U.S. governement, there perhaps will never be another revolutionary turned sexual icon as provocative as Hef. Happy Birthday, Mr. Playboy.


1. HEF TURNS THE GIRL NEXT DOOR INTO A SEX SYMBOL
By the time Hef published the first issue of Playboy, which featured Marilyn Monroe on the cover as the first “Sweetheart of the Month,” Norma Jeane was already a Hollywood A-lister, having appeared in more than a dozen films, including the Oscar-winning All About Eve. While there couldn’t have been a better woman to grace Playboy’s first cover, Hef soon became more interested in spotlighting everyday woman in pictorials versus celebrities. Hence the birth of Playboy’s infatuation with the girl next door, the first of whom was Janet Pilgrim. An employee in Playboy Enterprises’s subscription fulfillment, the story goes that Janet agreed to become Miss July 1955 issue in exchange for some new office equipment. (Her pictorial is rare in that it also features Hef in the background.) Whether lawyers, doctors, surfers or equestrians, Hef has long celebrated the sex appeal of sexy, confident, whip-smart women who aren’t afraid to embrace their sexuality after hours. Surely, it’s a fantasy many young men adopted after finding their dad’s hidden stash.—Shane Michael Singh

2. HEF REMINDS US THAT READING IS SEXY
Who you kidding? Everyone reads Playboy for the articles. For 63 years, Playboy has married cutting literature from the world’s most legendary writers with artistic nude and semi-nude pictorials of the world’s most beautiful women, including Kate Moss, Marilyn Monroe, Pamela Anderson and Bo Derek. Somehow, Hef has found a way to make both equally intriguing. Aside from its legacy of fiction, including the introduction of James Bond and pieces from Ray Bradbury, Jack Kerouac and Kurt Vonnegut, Playboy built its literary reputation around sharp-witted cartoons from Harvey Kurtzman, Jules Feiffer and Shel Silverstein and Playboy Interviews with Martin Luther King Jr., Malcolm X, John Lennon and Jimmy Carter. The long-standing marriage between contrasting mediums is but one of many facets that sets Hef apart a visionary. Name us one other place you can get it.—Bobby Box

3. HEF PLAYED A ROLE IN ROE V. WADE
Through the Playboy Foundation, Hef has funded a range of legal battles, including Cotner v. Henry, which argued against Indiana’s sodomy statute, for which a man was imprisoned for three years after having anal sex with his wife. But perhaps most noteworthy are the cases that ultimately led to one of the most intensely debated Supreme Court decisions of all time: Roe v. Wade. “We were the amicus curiae in Roe v. Wade,” Hef says. “That’s a part of history very few people know.”

In 1971, Norma McCorvey (“Jane Roe”) filed a lawsuit against the Dallas County district attorney (Henry Wade) claiming that a Texas law criminalizing abortion violated her constitutional right to privacy. At the time Roe was decided, the majority of states restricted or outright banned abortion unless the procedure was necessary to save the mother’s life. In the now-infamous case, Roe claimed that while her life wasn’t endangered, she did have a right to terminate her pregnancy in a safe medical environment. In its 1973 7-2 decision, the Supreme Court ultimately ruled that the law violated the U.S. Constitution. It was and still is widely regarded as one of the most distinguished wins for women’s rights.—Bobby Box

4. LET’S TALK ABOUT THE BUNNY SUIT
As Comedy Central’s Derek Waters wrote in 2015 in The Drunk History of Playboy, “Hef’s greatest feat may be that he made a rabbit sexy. You have to be a genius to look at a rodent and say, ‘You know, it’s sort of sexy. Not so much the eyes, the legs, the nose or the feet…but those ears and tail are damn sexy. Sold.’”

Well put. Originally created as a uniform for the Playboy Club, the Bunny costume has since become an international symbol of sex, pleasure and the good life, even holding a place in the Smithsonian as a “true national treasure.” It is also the only service uniform to earn a U.S. patent. Trivia: the original costume came in 10 colors and featured no cuffs and colors; those were added in 1962. It has since been reimagined by designer Roberto Cavalli and worn by Paris Hilton, Dolly Parton, Barbara Walters, Carrie Fisher and Reneé Zellweger—not to mention thouands of women every Halloween. Hef of course then made the men’s version: silk pajamas. Honestly, if we had to limit this list to just one entry, Hef making rabbits sexy without venturing into zoophilia might be the shoo-in.—Shane Michael Singh

5. ONE NAME: PAMELA ANDERSON
Let’s be blunt: Without Playboy, would the world have ever come to know Pamela Anderson? Perhaps—we believe her beauty is so transcendant someone would have discovered her sooner or later—but when Hef asked Pamela to be in Playboy, the 22-year-old Canadian was just a girl at the ballpark with a dream of leaving Vancouver Island. A record 14 covers later, Pamela Anderson has come to define the blonde bombshell and sexual magnetism, from her roles on Baywatch and Home Improvement to her animal activism. In 2016, Pamela said this to James Franco of her unexpected fame: “I never wanted to be in this industry; I didn’t know the option existed for me. But I guess I’ve done pretty well for myself just going with the flow. And then the work never ended.” While all credit of success is due to Pamela for her vivacious, addictive persona, we do have to hand a smittance to the man who first saw the sparkle.—Shane Michael Singh

6. TMW HEF TURNED A MEN’S MAGAZINE INTO A POLITICAL MOVEMENT
Hef founded the Playboy Foundation, the publication’s corporate giving program, in 1965 to pursue, perpetuate and promote the principles of freedom and democracy. This was two years after Hef was arrested in Chicago on charges of publishing and circulating obscene material. The foundation donated to many worthwhile causes, including genetic testing, breast cancer research, human sexuality research and civil rights lawsuits, as mentioned above. Since its inception, the Playboy Foundation has given more than $20 million in cash grants, contributions and in-kind services to nonprofit organizations throughout the United States, all with one common goal: to protect the rights of the individual in a free society. Now that’s sexy.—Bobby Box

7. DARINE STERN NABS HER OWN PLAYBOY COVER
In October 1971, 18 years after the launch of Playboy, Hef redefined a standard of mainstream beauty by giving African American model Darine Stern her own cover. This now-iconic image, which features Stern seductively slouched over a Rabbit Head office chair, was controversial as nude images of black women were mostly reserved for publications created for and by the black community. Though this was the first time a black woman appeared solo on a cover, Playboy had already featured two black Playmates, Miss March 1965 Jennifer Jackson and Miss October 1969 Jean Bell. In 2005, the American Society of Magazine Editors named Stern’s as one of the most important magazine covers of the past 40 years.—Bobby Box

8. WE HAVE TO TALK ABOUT MARGE SIMPSON, RIGHT?
To celebrate The Simpsons’s 20th anniversary, Hef featured Marge Simpson, the matriarch of the wonderfully dysfunctional yellow family, on Playboy’s November 2009 cover and in a five-page pictorial, making her the first cartoon character (and blue-haired model) to achieve the honor. The tongue-in-cheek move was unexpected not just because Marge is fictional, but also because the character had proved herself to be quite the modest girl over two decades on television. For the interview, Playboy editors sent questions to Matt Groening and The Simpsons’s writing staff in order to ensure the feature, titled The Devil in Marge Simpson, was as authentic to TV’s favorite mom as possible. For the pose, Marge’s cover mirrors that of Diane Stern’s, nodding to the latter’s iconic and groudbreaking status. “Marge Simpson is the quintessential girl next door who stole our hearts 20 years ago and has held them captive ever since. We were delighted to learn she wanted to grace the pages of our magazine. Her pictorial is truly stunning,” Hef said.—Bobby Box

9. HEF PUBLISHES THE CROOKED MAN
In August 1955, Hef published sci-fi writer Charles Beaumont’s The Crooked Man. The plot: A man named Jesse must hide his heterosexuality in a reverse society where everyone is gay and it’s criminalized to be straight. One only has to consider the political climate at the time to understand why the publication of The Crooked Man, in a men’s magazine no less, was so important—and controversial.

Before 1962, sodomy, whether solicited or consensual, was a felony in every state, essentially outlawing homosexuality. Gays, of course, weren’t allowed to serve in the military and they could be openly discriminated against. The Lavendar scare, a McCarthy-era witch hunt for gays, was also at its peak, and law enforcement would often raid underground gay bars or entrap gay men and women by feigning interest in them. Thus, publishing a piece of fiction that flipped heterosexuality into oppression ruffled some milquetoast feathers. A longtime LGBT advocate, Hef had this to say to the naysayers: “If it was wrong to persecute heterosexuals in a homosexual society, then the reverse is wrong, too.”—Shane Michael Singh

10. HEF BATTLED WILLIAM BUCKLEY OVER THE PLAYBOY PHILOSOPHY
At the time of Playboy’s founding, progressive attitudes about sex outside of traditional, heterosexual and monogamous relationships were virtually unheard of. Then came Hef’s Playboy Philosophy in December 1962. The 25-part series, featuring 160 pages of essays published over four years, tackled the underpinnings of sociosexual values and regulations, from divorce, STDs and birth control to feminism and court-decided obscenity. The views expressed therein landed Hef on television in a debate on Christianity and sexual mores with the conservative William F. Buckley Jr. on Firing Line. “The Philosophy is a response to the Puritan part of our culture,” he said. “Significant technological advances have permitted the opportunity to examine sex in a new context that is not totally related to procreation. This search for a new ethical set of moral values based on something other than simply rigid rules set forth centuries ago is something form which only good can come.”

To this day, many label Hef as an ignitor of America’s mid-century sexual revolution, and no matter what line you fall on in that debate, you can’t deny that his open-minded approach to sex has massively influenced how both men and women own their sexualities, instead of being shamed by it. The ultimate litmus test of how far we’ve come—and how far we have to go? Pick up a Playboy and any other magazine, put both on your coffee table and see which copy guests pick up first. We bet some stimulating conversations about sex will be had no matter the outcome.—Shane Michael Singh