The Monthly
Comic strip by Hugh Hefner. 

Hugh Hefner was a U.S. publisher and editor, worldfamous as the founder of Playboy, the most iconic men's magazine in the world. In that regard, he was also the only magazine publisher to reach such universal recognizability. Between 1953 and 2016, he was Playboy's chief editor, creative advisor and publisher, a feat which landed him in the Guinness Book of Records for being the longest-running chief editor of a magazine. Playboy was the first "nudie magazine" in the world and therefore managed to become a multi-million dollar enterprise with various media outlets. It broke the market for countless similar erotic magazines. Yet contrary to them, it strove for a classy, dignified status. Playboy discussed sex in an open manner. Various celebrity models, actresses and pop singers saw it as an honor to pose nude in its pages. The legendary parties at the Playboy Mansion gave the impression of a fun and open atmosphere, although in later years stories came out of toxic behavior and abuse. Still, Playboy stood at the forefront of the sexual revolution, which exploded during the 1960s and 1970s. Hefner used his magazine as a platform for freedom of speech. He vocally supported sexual liberation, civil rights for black people and the LGBT community. The magazine offered quality interviews, articles, columns, cartoons and comics.  Many artists whose work was too free-spirited and risqué to be published in regular magazines found a well-paid spot in Playboy's pages. Hefner also produced Harvey Kurtzman's short-lived comic magazine Trump. Few people know that Hefner actually began his career as a cartoonist, though not with the same success as his later Playboy enterprises.

Early life 
Hugh Marston Hefner was born in 1926 in Chicago, Illinois. His parents were very conservative Methodists who both worked as teachers. Hefner showed an interest for publishing at a young age. As president of the student council, he founded a school paper for which he wrote articles and drew cartoons. Hefner's favorite comics during his youth were Alex Raymond's 'Flash Gordon' and Milton Caniff's 'Terry and the Pirates'. He even acknowledged that he started smoking a pipe because of the 'Terry' character Pat Ryan. In 1944, he was drafted into the U.S. Army and worked for its newspaper. Back in civilian life, Hefner studied at the University of Illinois, where he achieved a bachelor of arts in psychology and a double minor in creative writing and art. 

High school diary by Hugh Hefner.

Hefner wrote and drew several cartoons for the campus newspaper, the Daily Illini. He later established his own humor magazine too, Shaft. All his cartoons rely heavily on inside jokes about daily life in school and at the campus. During lessons, he scribbled and doodled down notes about what his fellow schoolmates said, did and wore. Later that afternoon and evening, he worked everything out in little comic strip-like cartoons, hand-colored with crayons. The drawings were somewhat stiff and at times chaotic by lack of frames to separate individual scenes. For anyone not present at Hefner's school at that time they are incomprehensible, but his fellow students enjoyed them a lot. One of them, Jane Sellers, saved them because she was confident that he was "destined to do amazing things." Thanks to her, these cartoons were rescued from obscurity and possible destruction. The student council voted Hefner not only as "Class Humorist", "Best Dancer", "Best Orator" and "Most Popular Boy", but also as "Most Artistic" and "Most Likely to Succeed in Life".

After graduation, Hefner made a new series of cartoons with a more professional look, aimed at a general audience. Most publishers rejected them, although some appeared in print in the satirical book 'That Toddlin' Town: A Rowdy Burlesque of Chicago Manners and Morals' (Chicago: Chi Publishers, 1951). It's not difficult to understand why they didn't catch on. Most lack funny punchlines and only show glimpses of his future Playboy persona. Realizing his own limits, Hefner pursued a career as editor instead. In 1949, he worked as an assistant personnel manager for the Chicago Carton Company. A year later, he became advertising copywriter for Carson Pirie Scott Department Store and, starting in 1952, for Esquire magazine. Low payment eventually convinced Hefner to found his own magazine, which he called Playboy.

Playboy was a serious gamble. Hefner mortgaged all of his furniture on top of all his other loans. He was so unsure that the first issue wasn't even dated. As fate would have it, the title became an unprecedented over-nite sensation. Sales rose with every issue until it became a multi-million dollar enterprise and one of the most recognizable brands in the world. Hefner had found a genuine hole in the market. Most media at the time were so prudent that sex was a complete taboo, or, particularly in the United States, presented as something shameful. Playboy was the first magazine to offer uncensored female nudity in each issue. Attractive young women were chosen as "Playmate of the Month". In the center of the magazine, a large folded nude photograph of the Playmate was featured. Hefner named this a "center-fold" or "fold-out", which became a neologism. In fact, the equally legendary "fold-ins" by Al Jaffee in Mad Magazine were inspired by this phenomenon.

Playboy not only showed nudity and sex, it embraced and discussed it in an open-minded way. A virile rabbit in bowtie, designed by Art Paul, became the company logo. The young women who worked at Playboy's headquarters or appeared as Hefner's female companions during public appearances were all dressed in trademarked bunny suits. Hefner cultivated the idea of the "playboy", a cool and suave man who was popular with the ladies and whose main life goal was the fulfillment of his personal dreams. Setting the example himself, the succesful editor bought a large luxurious house in Holmby Hills, Los Angeles, California - the Playboy Mansion - where he organized weekly all-night parties. Fancy dinners, cool drinks, smooth jazz, game activities, celebrity guests and willing young women were present at every occasion. Many celebrities went to Playboy's parties without any fear or embarrassment of hurting their public reputation. Hefner felt so comfortable in his self-created little world, that he wore nothing but silk pajamas and slippers, even during public appearances. Regular broadcasts of late-night TV shows such as 'Playboy's Penthouse' (1959-1960), 'Playboy After Dark' (1969-1970) and 'The Girls Next Door' (2005-2010) further popularized his image. He sparked the imagination of many men and became a hero in their eyes.

Playboy also played a significant role in addressing social and political issues. Hefner advocated freedom of speech, sexual liberation and support of African-American and homosexual civil rights. In 1955, Playboy broke new ground by publishing Charles Beaumont's short story 'The Crooked Man' which criticized homophobia. The TV show 'Playboy's Penthouse' (1959-1960) broke new ground by having white and black performers sharing the screen. The Playboy Clubs pushed the same policy, despite the segregation laws in some states. When Playboy started publishing its praised interviews in 1962, African-American jazz legend Miles Davis was the first candidate. Other notable black celebrities interviewed in those early years were Martin Luther King and Malcolm X. Hefner raised money for various charitable causes. In 1979, he established the Hugh Hefner First Amendment Award for people who protect and enhance freedom of speech, as guaranteed in the U.S. constitution. In 1970, Playboy became the first men's magazine to be printed in braille.

Some of Hugh Hefner's Chicago cartoons.

Naturally, Hefner also drew criticism. Puritans, prudes and religious fanatics were outraged over his glorification of sex and nudity. In several parts of the world, Playboy was banned, particularly in most of Africa (except South Africa), the Middle East (except Lebanon and Turkey) and South-East Asia (except Hong Kong, Japan, Thailand, South Korea and the Philippines). Even Ireland banned the magazine between 1961 and 1995, as did the Australian province Queensland between 2004 and 2005. In some countries, Playboy was available with censored nudity, such as Japan. Feminists felt Playboy objectified and downgraded women as mere sex toys. In 1963, Hefner was sent to court for selling obscenity, referring to an issue which featured Hollywood actress Jayne Mansfield in the nude. He won his case. In 1986, U.S. Attorney General Ed Meese organized a special anti-pornography commission, backed by the religious right movement the Moral Majority. Playboy was a prime target for their smear campaign. Hefner sued them, won his case and Meese was forced to publicly clear the magazine of all accusations. 

Reputation and achievements
Both Playboy's hedonistic image and bad press have often led to the misconception that it was nothing but a porn magazine. In reality, it had a far more classy reputation than publications like Hustler, Screw or Penthouse. The featured nudity was never vulgar. Various high-profile professional photographers such as Ken Marcus, Annie Leibovitz and Helmut Newton were hired to make the pictures elegant and tasteful. As such, it became less a shame and more an honor to be published in Playboy. Many female celebrities posed for the magazine, often for huge amounts of money: Marilyn Monroe, Bettie Page, Jayne Mansfield, Nancy Sinatra, Kim Basinger, LaToya Jackson, Farrah Fawcett, Samantha Fox, Carmen Electra, Sharon Stone, Charlize Theron, Madonna and Lindsay Lohan.

The centerfolds were also just a small aspect of the actual content. As Hefner put it, Playboy advocated "entertainment for men" which had a wider scope than just sex. The magazine gained recognition for high quality interviews, articles, columns, reviews, photographs, comics and cartoons by renowned journalists, novelists, writers, critics, photographers and illustrators. The global enterprise has its own record label (Playboy Jazz All-Star Records, 1957-1972, Playboy Records, 1972-1978), jazz festival (1959), night clubs  (Playboy Club, 1960), philanthropic organization (Playboy Foundation, 1965), TV channel (Playboy Channel, 1982) and radio channel (Playboy Radio, 2006). Their film company Playboy Productions Films, produced such pictures as Roman Polanski's 'MacBeth' (1971), the Monty Python debut film 'And Now for Something Completely Different' (1971) and also donated money to the production of Ralph Bakshi's 'Fritz the Cat' (1972).  

Playboy cartoons
While Hefner's own cartooning career had been forgettable and unnecessary once Playboy conquered the world, he remained fond of the medium. Many illustrators, comic artists, cartoonists and graphic designers were invited to decorate Playboy's pages. Already in its second issue, Hefner received permission from Milton Caniff to publish 'Male Call', a comic rejected elsewhere for being too risqué. This earned Playboy a reputation as the most open-minded magazine for free-spirited and sexy artwork. A typical Playboy cartoon featured naughty, but tasteful gags about nude, sexy men and women. Hefner kept a close watch on the overall look and style. It wasn't enough for a cartoon to be funny. Both the situation and female characters had to look fun, appealing and titillating. While Hefner's creative control has sometimes been controversial, Playboy was still a godsend for many young artists. Artwork which was too risqué for regular magazines was warmly welcomed at Hefner's place. He not only offered the finest quality printing, but paid extraordinarily well. 

Among the most regular contributors in Playboy were Rowland B. Wilson, J.B. Handelman, Al Stine, Jules Feiffer, Erich Sokol, Gahan Wilson, Charles Rodrigues, Gardner Rea, John Demsey, Kiraz, Alden Erickson, Charles W. Miller, Claude, Jerry King, Don Flowers, Alberto Vargas, John Held Jr., Doug Sneyd, Richard Taylor, Phil Interlandi, E. Simms Campbell, Marty Murphy and Roy Ramonde. Jack Cole, best known as the creator of 'Plastic Man', worked four years for the magazine until his untimely suicide in 1957. Hefner was one of only two people (the other being Cole's wife) whom he sent a suicide letter. In 1966 Tomi Ungerer became editor of a food column in the magazine. Some of the longest-running comic series in Playboy were Dean Yeagle's 'Mandy', Eldon Dedini's 'Satyr & Nymph', B. Kliban's 'Cat', Robert "Buck" Brown's 'Granny' (1963-2007) - and perhaps the most iconic - Harvey Kurtzman and Will Elder's 'Little Annie Fanny' (1962-1988). Shel Silverstein drew 23 comic strip versions of travels he made across the world for Playboy under the title 'Shel Silverstein Visits...'. Bobby London's 'Dirty Duck' found a haven in the magazine between 1976 and 1987. In the 1980s, Gene Schwimmer scripted the superhero parody comic 'Through Space and Time with Schwimmer and Jones', drawn by Randy Jones

People like Eli BauerJack Davis, Paul Coker, John Caldwell, Art Spiegelman, Zack Poitras, Randy JonesJohn Jonik, Roger Licot, Lee Lorenz, Natalia Forcat, Bruce McCallDick Oldden, Don Orehek, Neon ParkCliff RobertsArnold Roth, Rogério Vilela, P.C. Vey, Cau Gomez, Murad GumenBill Asprey, Jay Lynch, Skip WilliamsonBill Woodman and Charles Burns have all at one point published erotic cartoons in Playboy's pages. In 2009 Playboy featured the first and only fictional character on its cover, namely Marge Simpson from Matt Groening's animated TV series 'The Simpsons'. Inside she could be seen in more revealing poses.

The two covers of Trump magazine.

As a huge fan of Harvey KurtzmanJack Davis and Wallace Wood, Hefner tried to have these cartoonists sign an exclusive contract to publish in Playboy. In 1956, Kurtzman resigned as Mad Magazine's chief editor after a financial dispute with publisher and co-editor William M. Gaines. Hefner offered Kurtzman a chance to create a new satirical comic magazine aimed at more mature readers, which he would produce. Kurtzman liked the offer, not only because the pay was better, but because Hefner was more open to his ideas than Gaines. In January 1957 the first issue of this new magazine, Trump, rolled from the presses. Just like Mad, it also featured satirical comics, though the format was more luxurious and with more emphasis on jokes about sexual topics. Several Mad cartoonists went on board, among them Jack Davis, but also Will Elder, Al Jaffee and another E.C. Comics regular Russ Heath. Only Wallace Wood eventually decided to stay loyal to Mad since he didn't want to work exclusively for Trump. Among the newer names were R.O. Blechman, Ed Fisher, Irving Geis, Roger Price and Arnold Roth and writers like Max Shulman (famous for 'Dobie Gillis'), Doodles Weaver (a member of Spike Jones' band) and future comedy film director Mel Brooks.

While Trump sold well, Kurtzman far exceeded the budget Hefner had given him. Unfortunately this happened at a time when Playboy's major distributor, American News, was soon to become bankrupt in June 1957. In order to keep out of debts Hefner tightened his belt. He took himself off salary, gave his senior executives pay cuts and placed a quarter of Playboy's stock as collateral so he could loan some money. To his own regret he had to axe off Trump as well. He personally went to Kurtzman to tell him the bad news. To make matters worse Kurtzman's wife had just given birth to their third child, Elizabeth. Kurtzman was so devastated that he started crying, for Trump was the closest he ever got to making "the perfect humor magazine." Years later Al Jaffee heard from Playboy's chief financial officer Bob Preuss that Hefner was also concerned that Kurtzman would never be able to make his deadlines. In either way the final issue of Trump came out in March 1957. Yet Hefner did have the decency to let Kurtzman advertize for his next comic magazine Humbug in a lengthy article in the December issue of Playboy that same year. 

Cover of the first issue of Playboy, with autograph by Hugh Hefner.

Media appearances and cameos
Hefner was one of the interviewees in the cult documentary 'Comic Book: The Movie' (1989). He was special guest voice in the Simpsons episode 'Krusty Gets Cancelled' (1993). Another episode, 'All's Fair in Oven War' (2004) is a homage to Playboy, where Bart and Milhouse remodel their treehouse based on the magazine's lifestyle. Hefner also voiced himself in Seth MacFarlane's 'Family Guy', namely the episode 'Airport '07' (2007) where he meets the sex-obsessed character Glen Quagmire.

As a colorful celebrity, it comes to no surprise that Hefner has had cameos in several comics too. In issue #17 (July 1970) of Playboy, Robert Crumb had his characters Mr. Natural and Angelfood McSpade visit the Playboy Mansion in an episode of Harvey Kurtzman and Will Elder's 'Little Annie Fanny'. In the episode Hefner laughs at Angelfood in her Playboy Bunny outfit, which makes her angry and causes them to be thrown out. In the 1980s Dutch comic artist Dick Matena made a series of one-shot comics about celebrities, one of which starred Hefner. Chester Brown made a graphic novel, 'The Playboy' (1990), which deals with his feelings of guilt when he read Playboy as a teenager. In issue #392 (April 2000) of Mad Magazine Hefner was featured in 'Mad's Celebrity Snaps', holding an issue of Mad Magazine.

In 1963 Hugh Hefner won the Ace Award, awarded by the National Cartoonist Society to celebrities who once aspired to become a cartoonist, but whose path led them to an entirely different career. In 1980 Hefner received a star at the Hollywood Walk of Fame. Four years later a marsh rabbit species was named after him. The Playboy publisher also made the Guinness Book of Records twice. Once for being the longest-running magazine editor in the world, secondly for owning the largest personal scrapbook collection in the world. 

Final years, death and legacy
Playboy's heydays spanned from the 1950s until the late 1990s. At their highest point, they were one of the best-selling magazines, with internatioal editions appearing all over the world. Halfway the 1970s, pornography was legalized in most Western countries. This made Playboy more socially accepted than ever, but at the same time many rival nudie magazines popped up. Several offered more explicit content, appealing to specific niches. Playboy lost some readers because of this, but their market viability remained strong. More serious rivals were the video stores that appeared in the late 1970s and Internet in the early 1990s, which made porn movies more readily available. All this gradually hurt Playboy's sales. As Hefner grew older, he became a self-caricature. Some younger generations saw him as a silly, somewhat pathetic old man surrounded by bimbos five generations younger than him. He still presented himself as a ladies' man in public, but by the turn of the 21st century he spent most of his days in the Mansion playing cards with his Bunnies. In 2009, Playboy had to reduce its publication schedule. By 2016, the magazine even quit its claim to fame: the full frontal nudity. Though they wisely came back on that decision by February 2017. Interestingly enough Hefner wasn't so concerned about removing nudity, but resisted the removal of cartoons far longer. Eventually even these had to go to remain financially saviable.

In October 2016, Hefner stepped down as chief editor, after 63 years of continuous editorship. His son Cooper took over the management. Nearly a year later, in September 2017, Hugh Hefner passed away. As stated in his will, he was buried next to Marilyn Monroe, as he bought the burial plot next to her tomb decades ago. In 2019 it was announced that Playboy would change from a monthly to a quarterly magazine. The final print issue of the magazine appeared in March 2020. Ben Kohn, Chief Executive Officer of Playboy Enterprises Inc., announced that the brand would continue its activities online.

Monte Beauchamp included Hefner in his book 'Masterful Marks: Cartoonists Who Changed The World' (Simon & Schuster, 2014), where Hefner's life story was adapted in comic strip form by Gary Dumm

In later years, it has become more public knowledge that Playboy's presented philosophy of sexual liberation was also a facade for mere chauvinist and predatorial behavior. In the 2022 A&E documentary series 'Secrets of Playboy', many former Bunnies, Playmates and Hefner girlfriends spoke out about what really went on behind closed doors. Most of the women were deemed disposable, and reports of sexual misconducts were swept under the rug. During the parties at the Playboy Mansion, Hefner's guests, including celebrity sex offenders like Roman Polanski and Bill Cosby, could do whatever they wanted. On several occasions, women were groped, drugged and submitted to sexual acts without consent. Many of the orgies held in the Mansion were filmed by Hefner, who held the recordings for safekeeping. Whenever a Bunny from one of the Playboy Clubs was abused, Playboy sent its own "Cleanup Crew" to give medical care and convince the victim to keep quiet, all to safeguard the company's public appearance. Despite what went on behind the scenes, Playboy managed to keep its public profile clean, promoting sexual liberation and female empowerement.

Media about Playboy and Hugh Hefner
For those interested in Playboy's cartoons, the book 'Playboy 50 years. The Cartoons' (2004) is the most comprehensive collection. Hefner's own cartoons can be read in 'Hugh Hefner's Playboy' (Taschen, 2013). Brigitte Berman's documentary 'Hugh Hefner: Playboy, Activist and Rebel' (2009) focuses on Hefner's long and remarkable career. The film features interviews with Joan Baez, Tony Bennett, Pat Boone, James Caan, Dick Cavett, Tony Curtis, Dick Gregory, Jesse Jackson, George Lucas, Bill Maher, Pete Seeger, Gene Simmons and Dr. Ruth. 

Hugh Hefner by Robert Crumb
From: Robert Crumb's Art & Beauty Magazine #2, 2003.

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