When you think of 10 8216 playboy, images of sleek bunny ears, glossy pages, and Hugh Hefner’s legendary parties probably pop into mind. Yet beyond the glitz, the magazine has been a cultural touchstone, publishing short stories, interviews, and cartoons from literary heavyweights. Below, we count down ten historic firsts that shaped the brand, each a quirky slice of pop‑culture history.
10 First Issue
In December 1953, Hugh Hefner, a former promotional copywriter for Esquire, risked $7,600 of his own and investors’ money to launch Playboy magazine, never knowing if a second issue would ever materialize. Priced at 50 cents, the maiden issue moved 50,000 copies off the stands.
Although Hefner billed the publication as a “lifestyle” magazine, he openly admitted that sex would be “one important ingredient” in the mix. He later added, “If there was going to be a sexual revolution, I would be its pamphleteer.”
Hefner’s regular column, “Playboy Philosophy,” further clarified his worldview: “If a man has a right to find God in his own way, he has a right to go to the devil in his own way also.” He argued that organized religion was outdated and should not impose its values on those who disagreed. For Hefner, people who were open‑minded wanted to be seen as attractive sex symbols. He famously likened Playboy exploiting sex to the way Sports Illustrated exploits sports.
9 First Centerfold
Hefner’s gamble paid off spectacularly when he chose Hollywood legend Marilyn Monroe as the magazine’s inaugural Playmate. At the time, Monroe was a struggling actress who, in 1949, earned $50 for a nude photoshoot with photographer Tom Kelley. The images were sold to Western Lithograph Company, a Chicago firm that printed calendars.
A year later, Monroe’s acting career surged with roles in The Asphalt Jungle and All About Eve. Hefner purchased the nude shots from Western Lithograph for $500, and Monroe became the Sweetheart of the Month – later renamed Playmate of the Month – featured in the first issue’s centerfold. The public’s sympathy for Monroe, who had been near‑penniless when she posed, meant the exposure didn’t tarnish her career.
8 First African‑American Playmate
While Playboy has a checkered record on race, the magazine did feature pivotal civil‑rights voices, from Alex Haley’s extensive interview with Martin Luther King Jr. to conversations with Muhammad Ali, Sammy Davis Jr., and Malcolm X. In October 1971, Darine Stern became the first African‑American woman to appear solo on the cover.
Earlier, in March 1965, the magazine broke another barrier when Jennifer Jackson appeared as the first African‑American Playmate. Jackson never imagined she was helping to push racial boundaries; she later reflected, “I never looked at it like that. I guess I was the first, but in Chicago we had black doctors, dentists and businessmen living in our neighborhood.”
For decades she felt shame about her Playboy appearance, a sentiment that softened only after a 1999 reunion where she described the experience as giving her “closure.”
7 First Transgender Pictorial
Caroline Cossey, known in the modeling world as “Tula,” became the first transgender woman to grace Playboy pages. After a cameo as a Bond girl in the 1981 film For Your Eyes Only, she and the other Bond girls promoted the movie with a joint June 1981 pictorial in the magazine.
A year later, a scandal‑making headline in the British tabloid News of the World declared, “James Bond Girl Was A Boy,” thrust Cossey into the global spotlight. In September 1991, at her request, she returned to the pages for her own dedicated pictorial.
At the time, Cossey was fighting the European Court of Human Rights to have her gender legally recognized on her birth certificate. She saw the pictorial as a platform for her cause. The exposure led to TV interviews on shows hosted by Phil Donahue, Maury Povich, Howard Stern, Joan Rivers, and Arsenio Hall. Cossey later authored two books, including the 1991 memoir My Story.
6 First Murdered Playmate
When Dorothy Stratten, a 20‑year‑old Playmate, was murdered in August 1980, Hugh Hefner appeared as a “sybarite in mourning,” clad in his signature silk pajamas. Teresa Carpenter’s Pulitzer‑winning article, “Death of a Playmate,” chronicled Hefner’s hope of turning Stratten into a major star.
Stratten’s estranged husband and former manager, Paul Snider, shot her in the face on August 14, 1980. Carpenter wrote that Snider, like Hefner, was “itching for the big score,” though Hefner possessed “more class.”
Film producer Peter Bogdanovich later suggested in his memoir The Killing of the Unicorn: Dorothy Stratten that Hefner’s lifestyle contributed to her demise, stating that she “could not handle the slick professional machinery of the Playboy sex factory, nor the continual efforts of its founder to bring her into his personal fold, no matter what she wanted.”
Stratten had become Playmate of the Month for August 1979 and Playmate of the Year in 1980, landing a role in the 1981 film They All Laughed. She fell for director Bogdanovich, moving in with him after their collaboration. As her relationship with Snider soured, he first raped her, then shot her, and finally turned the gun on himself.
Hefner later told Carpenter he agreed to the interview to set the record straight, insisting Stratten was not a victim of “life in the fast lane” but rather of “a very sick guy [who] saw his meal ticket and his connection to power … slipping away.” Although several Playmates have died under mysterious circumstances, Stratten remains the first to be murdered.
5 First Nudity‑Free Issue
During the 1970s, Playboy boasted a circulation of roughly five million copies. By 2011, that figure had dwindled to 1.5 million, pressured by competitors like Hustler and Penthouse, the rise of free‑online pornography, and the magazine’s loss of status to up‑starts such as Maxim, Stuff, and FHM.
In response, executives decided a bold shift was needed. The iconic bunny logo had already been licensed for countless products, and the brand’s overseas market remained strong. The first nudity‑free issue debuted in March 2016, following the website’s removal of nudity in August 2014.
The experiment lasted only a year; naked models returned to the pages in 2017. Cooper Hefner, the chief creative officer, later admitted dropping nudity was a mistake. Former CEO Scott Flanders, who had dismissed nudity as “passe,” left the company in May 2016. Cooper summed up the reversal: “Today, we’re taking our identity back and reclaiming who we are.”
4 First Club
The inaugural Playboy Club opened its doors in 1960, turning the magazine’s fantasy into a real‑world lounge. The clubs resembled sleek bachelor pads, offering cocktails, décor, and the famed Bunnies—servers dressed in iconic tuxedo‑style outfits with cotton tails.
By the mid‑1980s, the last company‑owned club closed, but at their peak over 30 locations thrived across the United States and abroad, including Japan and the Philippines. London’s club, launched in 1966, attracted luminaries such as Julie Christie, Sidney Poitier, Ursula Andress, Peter Sellers, Woody Allen, David Frost, and Rudolf Nureyev. Tony Bennett, Johnny Carson, and members of The Beatles also frequented the venues.
Hefner named the servers “Bunnies” after Bunny’s Tavern in Urbana, Illinois, where he occasionally dined as a University of Illinois student. Bunnies faced strict rules: no dating fellow staff, no drinking on duty, and no chewing gum. A “Bunny mother” supervised them, ensuring they remained cheerful and cooperative with male patrons.
Uniform standards were meticulous—vivid lipstick, refrigerated hosiery, mandatory manicures, and no jewelry aside from the signature Playboy cuff links. When high‑heeled shoes fatigued their feet, Bunnies were instructed to roll them over an empty Coke bottle for relief.
Infractions incurred fines, but Bunnies could earn merits for overtime, private parties, and assisting managers. They arrived an hour early to apply makeup and dress, a period for which they were unpaid. Initially, Hefner envisioned frilly nightgowns akin to Ziegfeld Follies attire, but those proved impractical for lighting cigarettes and serving drinks.
Eventually, a collaboration with Playmate Ilse Taurins led to the final design: a female rendition of the Playboy logo, complete with criss‑cross lacing at the leg’s top, as Hefner insisted.
3 First Club Exposé
Feminist pioneer Gloria Steinem, later founder of Ms. magazine, went undercover as a Playboy Club Bunny for 17 days in May 1963. Her scathing exposé, “A Bunny’s Tale,” ran in the May and June 1963 issues of Show magazine.
While Hefner penned monthly essays he claimed were “the Emancipation Proclamation of the sexual revolution,” Steinem documented the stark contrast she witnessed inside the club. A wardrobe mistress forced a plastic bag into her bosom, and the club levied fees for mandatory services, including charging Bunnies for false eyelashes.
Perhaps most egregious, the club siphoned up to 50 percent of the Bunnies’ tips. Steinem’s narrative highlighted how servers endured patronizing and exploitative treatment, exposing a side of the Playboy empire that few had seen.
2 First Braille Items
In the 1980s, Senator Mack Mattingly of Georgia championed a congressional amendment that barred the Library of Congress from producing braille versions of Playboy features such as “Party Jokes,” “Ribald Classics,” and the “Playboy Forum.” The ban passed with bipartisan support, forcing the Library to cease those productions.
Blind enthusiasts of the magazine sued, arguing that the prohibition infringed upon their First Amendment rights. The courts ultimately overturned the ban, allowing the Library to resume offering braille editions of the previously prohibited items.
1 First Foreign Edition
The magazine’s inaugural foreign edition rolled out in West Germany in 1972. Since then, Playboy has been printed in Argentina, Australia, Brazil, France, Greece, Italy, Japan, Mexico, the Netherlands, Spain, and Turkey.
The first Chinese‑language issue printed 50,000 copies, selling out in just two days in Hong Kong. William Stokkan, president of the Playboy licensing and merchandising group, remarked that the “overwhelming reader response … underscores Playboy’s strength and ability to cross geo‑cultural boundaries.”
Leigh Paul, a devoted reader and writer, enjoys the magazine’s eclectic mix, even if arithmetic isn’t her strong suit.