Hugh Hefner, Playboy founder and leader of '60s sexual revolution, dies at 91

Hugh Hefner, who parlayed $8,000 in borrowed money in 1953 to create Playboy, the hot-button media empire renowned for a magazine enriched with naked women and intelligent interviews just as revealing, has died. He was 91.

Playboy announced the news, saying Hefner died in his home at the Playboy Mansion of natural causes on Wednesday.

While most famous for Playboy, the businessman dabbled in all forms of media, including hosting his own TV shows, beginning with Playboy’s Penthouse in the late 1950s and early '60s. Shot in his hometown of Chicago and syndicated, the show featured Hefner in a tuxedo and smoking a pipe surrounded by “playmates” and interviewing such celebrities as Bob Newhart, Don Adams and Sammy Davis Jr.

66 PHOTOS
Hugh Hefner through the years
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Hugh Hefner through the years
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26: Playboy Magazine founder and publisher Hugh Hefner attends a party in his honor with actresses Joan Bradshaw (right) and Susanne Sidney on June 26, 1957 in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner and guest at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw and girls at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
American pornographer Hugh Hefner and murdered Playboy PLaymate Dorothy Stratten (1960 - 1980), 1980. She holds a plaque naming her 1980 Playmate of the Year. (Photo By Julian Wasser/Online USA Inc./Getty Images)
American publisher Hugh Hefner smokes a pipe and holds a pamphlet while balancing a briefcase on his knee, c. 1960. (Photo by Authenticated News/Getty Images)
Show Business Illustrated magazine
(Original Caption) 1/29/1962 -New York,NY -: Hugh M. Hefner, Editor and Publisher of Playboy, is shown with Cynthia Maddox, the blond cover girl on the February issue of his magazine, arriving by TWA superjet from Chicago. They are here to attend a party given by Ella Fitzgerald at the Basin Street East in honor of winners of the Playboys jazz poll.
(Original Caption) Hugh Hefner, publisher of Playboy Magazine, shown as he appeared in court to face charges that nude photograph of Jayne Mansfield in the June issue are obscene. Hefner's attorneys asked for a continuance and his trial was set for July 9 in Municipal Court.
26th June 1966: American millionaire Hugh Hefner, founder of the Playboy empire, during a visit to Britain. (Photo by John Downing/Express/Getty Images)
Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. (Photo by Dove/Getty Images)
Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Hugh Hefner Boss of the Playboy Empire arrives with an entourage of Bunny Girls at London Heathrow Airport, Saturday 25th June 1966. Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Playboy CEO Hugh Hefner with partner model, actress and singer Barbara Benton arrive at Paris Airport. (Photo by James Andanson/Sygma via Getty Images)
(GERMANY OUT) Hefner, Hugh *09.04.1926-Verleger (Playboy), USA - mit seiner Freundin Barbara Benton waehrend eines Besuchs in Berlin- 1969 (Photo by Binder/ullstein bild via Getty Images)
Portrait taken on August 21, 1970 at Le Bourget airport shows US Playboy Magazine publisher Hugh Hefner and his girlfriend actress Barbara Benton. AFP PHOTO (Photo credit should read STRINGER/AFP/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner (Photo by Michael Ochs Archives/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner Photo by Michael Ochs Archives/Getty Images
Publisher Hugh Hefner and Actress Julie Newmar attend the Rugby Ball on October 20, 1972 in New York City, New York. (Photo by Ron Galella/WireImage)
HUGH HEFNER -- Pictured: (l-r) Hefner's girlfriend/Singer, Barbi Benton, unknown, Playboy founder Hugh Hefner discussing promotional artwork for Barbi's 1974 debut album 'Barbi Doll'-- Photo by: Ron Tom/NBCU Photo Bank
American publisher Hugh Hefner, of Playboy Enterprises, smiles with his girlfriend, American actor and model Barbi Benton as they attend the 21st annual SHARE fund raiser for The Exceptional Children's Foundation. She wears a feathered blouse and he holds a pipe. (Photo by Frank Edwards/Getty Images)
Hugh Hefner and bunnies during 5th Annual International B Bunny of the Year Pageant at The Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend Hugh Hefner's Special 25th Anniversary Party on January 10, 1978 at New York New York Disco in New York City. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend 25th Anniversary Party for Playboy Magazine on January 11, 1979 at Tavern on the Green in New York City. (Photo by Ron Galella/WireImage)
NEW YORK, NY - CIRCA 1979: Hugh Hefner and Sondra Theodore circa 1979 in New York City. (Photo by Images Press/IMAGES/Getty Images)
375250 01: Mid-1980's Playboy Mansion. Hugh Hefner and girlfriend Carrie Leigh at the Playboy Mansion.
Sondra Theodore and Hugh Hefner (Photo by Ron Galella/WireImage)
circa 1980: 'Playboy' magazine founder and publisher Hugh Hefner with 1980 Playboy Playmate of the Year, Canadian model and actor Dorothy Stratten. Stratten wears a strapless top and flowers in her hair. (Photo by Frank Edwards/Fotos International/Getty Images)
THE TOMORROW SHOW -- Pictured: (l-r) Playboy founder/publisher Hugh Hefner, journalist/Playboy covergirl Rita Jenrette at the Playboy Mansion -- Photo by: Paul Drinkwater/NBCU Photo Bank
Hugh Hefner and Carrie Lee attend the opening party for 'Private Lives' on October 13, 1983 at Madame Wu's Restaurant in Beverly Hills, California. (Photo by Ron Galella/WireImage)
Hugh Hefner and playboy bunnies are photographed October 29, 1985 at the re-opening of the Playboy Club in New York City. (Photo by Yvonne Hemsey/Getty Images)
Hugh Hefner and Carrie Lee attends the premiere of 'Beverly Hills Cop II' on May 19, 1987 at Mann Chinese Theater in Hollywood, California. (Photo by Ron Galella, Ltd./WireImage)
LOS ANGLES, CA - 1989: Playboy Magazine founder and publisher, Hugh Hefner, announces his engagement to Playmate of the Year Kimberly Conrad at a 1989 Los Angeles, California, press conference. Hefner and Conrad divorced in 2003. (Photo by George Rose/Getty Images)
368600 12: Hugh Hefner and friends, Jessica Paisley, left, Mandy Bentley and Sandy Bentley arrive for the 10th Anniversary celebration of the hit television show, 'Baywatch' on May 2, 2000 in Santa Monica, CA. The show has aired nearly 200 episodes since it first premiered in 1990. (Photo by Joe Thomas/Online USA)
Kimberly Conrad, Marsden Hefner, and Hugh Hefner during Christie Hefner Hosts Open House Gala for New Headquarters at Playboy Headquarters in Beverly Hills, California, United States. (Photo by Jim Smeal/WireImage)
Hugh Hefner and Kimberley Conrad in Photo Booth (Photo by Frank Trapper/Corbis via Getty Images)
Nancy Sinatra and Hugh Hefner attend Playboy Magazine Party on April 6, 1995 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
The Rembrandts, Yasmin Bleeth, Hugh Hefner & Playboy Bunnies (Photo by SGranitz/WireImage)
Hugh Hefner, wife Kimberly and their children during Premiere of 'Star Wars: Special Edition' In 1997 at Westwood in Westwood, CA, United States. (Photo by Magma Agency/WireImage)
Playmate Heather Kozar and businessman Hugh Hefner attend Playboy Announces Heather Kozar as the 1999 Playmate of the Year on April 29, 1999 at The Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
7/17/99 Los Angeles, Ca. Hugh Hefner Dancing With Playboy Gals At The Playboy Expo '99 & Playmate Reunion Held At The Pacific Design Center. (Photo By Brad Elterman/Getty Images)
7/16/99 Beverly Hills, CA Hugh Hefner, Shannon Tweed, and Diane Hunter (1954 Playmate) at the First-Ever Playboy Expo. The expo gave a chance for fans to meet centerfolds, celebrities, Bunnies, wirters, artists, photographers, and cartoonists. Photo Brad Elterman/Online USA, Inc.
CANNES, FRANCE: Playboy magazine president Hugh Hefner (C) poses with playmates 14 May 1999 on the steps of the Palais des Festivals before the screening of their movie 'Entrapment' in selection for the 52nd Cannes Film Festival. (ELECTRONIC IMAGE) (Photo credit should read PASCAL GUYOT/AFP/Getty Images)
BEVERLY HILLS, CA - APRIL 29: Hugh Hefner attends Playmate of the Year Press Conference on April 29, 1999 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
Brandi and Hugh Hefner during Madonna's new CD Music Party in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Madonna, Hugh Hefner & Playboy Bunnies (Photo by Kevin Mazur/WireImage)
WEST HOLLYWOOD, CA - DECEMBER 18: Playboy founder Hugh Hefner poses with unidentified model, Shauna Sand (2nd from L) and Holly Madison (R) during Barfly 5th year anniversary party on December 18, 2002 in West Hollywood, California. (Photo by David Klein/Getty Images)
Hugh Hefner and Playboy Playmates during Ben Stiller and Christine Taylor Host a Grand Classics Screening of 'Sweet Smell of Success' with YSL at the Playboy Mansion at Playboy Mansion in Beverly Hills, California, United States. (Photo by Donato Sardella/WireImage for Harrison & Shriftman)
Hiromi Oshima, Playboy Miss June 2004, Holly Madison, Hugh Hefner, Bridget Marquardt , Kendra Wilkinson, Sara Jean Underwood, Playboy Playmate of the Year 2007 and guest (Photo by Enos Solomon/FilmMagic)
Hugh Hefner and models during Hugh Hefner Inducted Into The Erotic Museum's Hall Of Fame at The Erotic Museum in Hollywood, United States. (Photo by Laurence Cottrell/FilmMagic)
(EXCLUSIVE, Premium Rates Apply) Carmen Electra and Hugh Hefner *EXCLUSIVE COVERAGE* (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Carmen Electra, top row far left, Hugh Hefner, center, The Girls Next Door and Playmates *EXCLUSIVE COVERAGE* ***Exclusive*** (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Hugh Hefner and girlfriends during The 21st Annual American Cinematheque Award Honoring George Clooney - Arrivals at Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Jason Merritt/FilmMagic)
LOS ANGELES, CA - DECEMBER 16: Playboy founder Hugh Hefner attends a book signing of 'Mr. Playboy: Hugh Hefner and the American Dream' at Barnes N Noble bookstore on Tuesday December 16, 2008 in Los Angeles, California. (Photo by Byron Gamarro/Getty Images)
LAS VEGAS - MAY 15: (L-R) Model Hope Dworaczyk, Playboy founder Hugh Hefner and his girlfriend, December 2009 Playboy Playmate of the Month Crystal Harris, arrive at a party introducing Dworaczyk as the 2010 Playboy Playmate of the Year at the Rain Nightclub inside the Palms Casino Resort May 15, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
BEVERLY HILLS, CA - DECEMBER 10: Hugh Hefner and Pamela Anderson attend the Hugh Hefner book signing session at Taschen on December 10, 2009 in Beverly Hills, California. (Photo by Riccardo S. Savi/Getty Images)
LOS ANGELES, CA - DECEMBER 09: Playboy founder Hugh Hefner (L) and model Crystal Harris attend an event celebrating the expansion of Griffith Park at Lake Hollywood Park on December 9, 2010 in Los Angeles, California. (Photo by David Livingston/Getty Images)
LOS ANGELES, CA - OCTOBER 13: Hugh Hefner attends 'The Rum Diary' Los Angeles Premiere at LACMA on October 13, 2011 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
BEVERLY HILLS, CA - SEPTEMBER 19: Playboy Founder Hugh Hefner (C) arrives at the 2011 Ella Awards at The Beverly Hilton hotel on September 19, 2011 in Beverly Hills, California. (Photo by Paul Archuleta/FilmMagic)
BEVERLY HILLS, CA - AUGUST 07: (L-R) Hugh Hefner and Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises ribbon-cutting ceremony for Beverly Hills Playboy World Headquarters on August 7, 2012 in Beverly Hills, California. (Photo by Tibrina Hobson/WireImage)
HOLLYWOOD, CA - JUNE 15: Publisher Hugh Hefner attends a press conference at the 35th Anniversary Playboy Jazz Festival - Day 1 at the Hollywood Bowl on June 15, 2013 in Hollywood, California. (Photo by Rodrigo Vaz/Getty Images)
Los Angeles, CA - OCTOBER 25: Hugh Hefner and Crystal Hefner attend Playboy Mansion's Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Hugh Hefner (C) poses with Playboy Bunnies Playmate of the Year 2013 Raquel Pomplun (2nd L) and Miss December 2009 Crystal Hefner (2nd R) at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Rachel Murray/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Cooper Hefner (L) and Hugh Hefner pose at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LAS VEGAS, NV - FEBRUARY 20: Impersonator George Kane of Florida as Hugh Hefner presents an award during The Reel Awards 2017 at the Golden Nugget Hotel & Casino on February 20, 2017 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
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The show boosted his personal and professional reputation and promoted what eventually became known as the “Playboy Philosophy,” a lifestyle that included politically liberal sensibilities, nonconformity and, of course, sophisticated parties with expensive accouterments and the ever-present possibility for recreational sex – though Hefner maintained he was a relative late bloomer in that department, remaining a virgin until he was 21.

Hefner followed that show with Playboy After Dark, which had a similar format but with more rock 'n’ roll, including appearances by The Grateful Dead, Three Dog Night, Harry Nilsson and Linda Ronstadt. The syndicated Screen Gems show was taped at CBS in Los Angeles and ran for 52 episodes in 1969-70.

Hefner also co-produced hundreds of Playboy-branded videos and a few feature films, such as Roman Polanski’s Macbeth and Monty Python’s first film, And Now forSomething Completely Different, both released in 1971. He had been a sought-after guest on TV shows as far back as 1969 when he played a Control agent in an episode of Get Smart, and more recently he appeared on Curb Your Enthusiasm, Entourage and Sex and the City as well as in animated shows like The Simpsons and Family Guy.

Read more: Hugh Hefner: The Playboy Interview

Hefner also made cameos in several movies, most recently 2008’s The House Bunny, which told the fictional story of a Playboy “bunny,” played by Anna Faris, who has been kicked out of the Playboy Mansion, the famous real-life, 22,000-square-foot house in Los Angeles where Hefner lived for more than four decades and where he hosted famously decadent parties that attracted celebrities A-list through D.

The house sold for $100 million in August with the provision that Hefner be allowed to live there the rest of his life.

Hefner became the unofficial spokesman for the sexual revolution that permeated the 1960s and '70s and he was both lauded and criticized by feminists of the era, with some accusing him of objectifying women while others said he liberated and empowered them. During a conversation with Gloria Steinem in 1970, Hefner dismissed feminism as “foolishness,” and Steinem told him: “What Playboy doesn’t know about women could fill a book ...; There are times when a woman reading a Playboy feels a little like a Jew reading a Nazi manual.”

Hefner was a staunch supporter of abortion – including helping to finance the landmark Rowe v. Wade decision in 1973 — and more recently was an outspoken advocate of same-sex marriage, and his dedication to such issues (along with his distribution of pornography) made him a pariah in some religious circles. “By associating sex with sin, we have produced a society so guilt-ridden that it is almost impossible to view the subject objectively,” he wrote in 1963 in one of his many broadsides aimed at Christian leaders.

Hefner also launched the Playboy Channel in 1982, a premium cable outlet that has since been sold and rebranded Playboy TV and is more explicitly sexual than when it was under his purview. He created The Playboy Club nightclub chain that still exists as a novelty, but in its heyday in the 1960s, the era’s biggest stars – including Rat Packers Frank Sinatra and Dean Martin — could be spotted holding court while food and drink were served by the barely dressed bunnies. All this was loosely reflected in the NBC series The Playboy Club, which was set in 1961 and canceled in 2011 after just three episodes aired.

Read more: Hugh Hefner Speaks Out About 'Playboy Club' Cancellation

Playboy magazine, though, was Hefner’s bread and butter and his first love. He created it as a young man three years removed from earning a bachelor’s degree in psychology from the University of Illinois at Urbana-Champaign and a few years after quitting a job as a promotional copywriter at Esquire. He borrowed $1,000 from his mom and $7,000 from more than 40 other investors for a publication he was set to call Stag Party until he discovered a magazine called Stag already existed. He purchased a picture of a naked Marilyn Monroe that was taken before she was famous and put it on the cover of his magazine, which he renamed Playboy. The first issue hit newsstands in December 1953.

He didn’t bother putting a date on it because he was doubtful there’d be future issues, but it sold 54,000 copies – 80 percent of the total he had printed -- and his largely male audience thirsted for more. The iconic mascot, a silhouette of a bunny in a bow tie, made its debut in the second issue, chosen because Hefner thought rabbits carried “sexual meaning” and were “shy, vivacious, jumping” animals.

Through the years, Hefner convinced many Hollywood starlets to reveal more of themselves on his pages than perhaps anywhere else, with Barbra Streisand, Madonna, Mariah Carey, Lindsay Lohan, Kate Moss, Dolly Parton, Sally Field, Joan Collins and Drew Barrymore among the many who warranted in-depth cover stories or Q&As accompanied by sexy pictorials. The “Playboy Interview” launched in 1962 when the magazine hired Alex Haley to interview jazz legend Miles Davis, and subsequent subjects included filmmakers Stanley Kubrick and Woody Allen, actresses Mae West and Bette Davis, civil rights luminaries Dr. Martin Luther King Jr. and Malcolm X, writer-philosopher Ayn Rand and, in 1965, The Beatles.

38 PHOTOS
Celebrities react to Hugh Hefner's death
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Celebrities react to Hugh Hefner's death
American Icon and Playboy Founder, Hugh M. Hefner passed away today. He was 91. #RIPHef https://t.co/tCLa2iNXa4
A great man, entrepreneur and innovator. Your legacy lives on. #Hef https://t.co/36cRzlUPRw
RIP #Hef Thank you for being a revolutionary and changing so many people's lives, especially mine. I hope I made y… https://t.co/6Nz7oqYdfj
Hugh Hefner was a GIANT in publishing, journalism, free speech & civil rights. He was a true original, and he was m… https://t.co/8ThS9oAAGm
RIP to the legendary Hugh Hefner! I’m so honored to have been a part of the Playboy team! You will be greatly missed! Love you Hef! Xoxo
Hugh Hefner was a strong supporter of the civil rights movement. We shall never forget him. May he Rest In Peace. https://t.co/oL3lKLZRQ5
So sad to hear the news about @HughHefner. 😢 #RIPHef https://t.co/IQiEYhMfvf
1st met him months B4 #SW opened-Expected stereotyped swinger/wildman not the kind-thoughtful loyal friend he alway… https://t.co/RPOBh7ZuxE
I met Hugh Hefner at the Playboy mansion. He was very nice to my mom. Don't ask. #RIPHef
I had a number of great conversations and with Hugh Hefner. Was such an interesting man. True legend. What an end of an era!
I just found out @hughhefner died. Thank u for the time together, 2 covers& artistic freedom on my second shoot. you believed in my vision
Goodnight Playboy.
RIP @hughhefner 💛 thank you for making me part of the Playboy family. Sending lots of love and prayers to @crystalhefner
RIP HF. Few did more for writers, inc myself, breaking boundaries and helping Lenny fight for his 1st Amend Right… https://t.co/tj620dcXa1
Hugh Hefner put me in Playboy & ignited my career. I am forever indebted, Hef. You will forever live on as an icon of epic proportions. #RIP
RIP to the OG #HughHefner 🙏🏽 https://t.co/AVXwKU1V4A
We love you #hef #HughHefner https://t.co/gr5DXSH22D
Trailblazer. Icon. An American institution! Rest in that big grotto in the sky, Hugh Hefner! https://t.co/9rKnQERPgw
Rest In Peace Hugh Hefner. 🐇Dr. Buss treasured your friendship. You lived life your way. #Maverick #Playboy https://t.co/gdVZNGtiBW
@hughhefner ..when I did playboy he spoke words to me that affected my direction. he was a man the room would stop for when he entered #rip
RIP HUGH HEFNER
Today the world lost a legend. #HughHefner started my career. For 22 yrs I got to wish him happy new year at his ma… https://t.co/vmkyGpipfx
Wow...just read the news. Rest In Peace Hugh Hefner. Your legacy and soul shall live on!
RIP Hugh Hefner I went to so many of his parties at the Playboy mansion it was legendary you will never be forgotten
Rest in peace #HughHefner - he will forever be remembered as the Hollywood legend who lived life to the fullest.
R.I.P. to the legend Hugh Hefner https://t.co/0WopDrAH1h
If you were raised without a mom Hugh Hefner probably changed your life. Champion of great writing & freedom of speech & always kind to me.
RIP What a life!!!!
Hefner. A giant of cultural influence.
RIP to a true pioneer! Playa for life! We will miss you. #Playboy https://t.co/3G97CQa5d0
Thank you, Hef, for Playboy. And thank you for what you did for me. You've left such an impact on the world...you'l… https://t.co/4NYB5IZ7Jy
We’ve lost a true explorer, a man who had a keen sense of the future. We learned a lot from you Mr. Hefner. #HughHefner
One of the nicest men I've ever known. Godspeed, Hugh Hefner. https://t.co/457cchqskO
RIP my friend. You changed the world.
As per his wishes, Hugh Hefner’s body will be left in a fort in the woods for other kids to find & pass around.
Hugh Hefner put me in Playboy & ignited my career. I am forever indebted, Hef. You will forever live on as an icon of epic proportions. #RIP
RIP hef. You were always sweet to me on movie nights at the mansion. Love to you @crystalhefner xo #RIPHef
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In a 1971 interview, John Wayne complained about “perverted films” coming from Hollywood and in 1976, presidential candidate Jimmy Carter famously uttered, “I’ve committed adultery in my heart many times.” Through the years, a running joke among men became that they buy Playboy not for the pictures but for the articles, though it rang true because some of the most notable writers in modern history appeared in the magazine, including John Steinbeck, Ray Bradbury, Ian Fleming, Kurt Vonnegut, Norman Mailer and Jack Kerouac.

Playboy Enterprises, the umbrella company Hefner founded in 1953, has fallen on hard times on a few occasions. Long gone is the Big Bunny, the private jet Hefner used decades earlier, and layoffs have plagued the enterprise, which went private in 2011 after years of a declining stock prices. In 2008, it was reported that Hefner had resorted to selling tickets to his famous parties at the Playboy Mansion with the proceeds going to Playboy Enterprises. Hefner’s daughter, Christie, ran the company for more than 20 years but left in 2009.

The magazine underwent a redesign in March 2016 that eliminated nude photos from its pages, but that practice did not last long.

Hugh Marston Hefner was born April 9, 1926, in Chicago to parents Glenn and Grace Hefner; a brother, Keith, came three years later. He has described his upbringing as “puritan” and “repressive” and said, “In many ways, it was my parents who, unintentionally, developed the iconoclastic rebellion in me.” However, in the book Mr. Playboy: Hugh Hefner and the American Dream, author Steven Watts suggests that Hefner’s formative years weren’t too much different than others of the era, except that his bedtime was a little earlier than that of his friends and his Sundays were reserved for church and family activities.

Also, there wasn’t a lot of outward affection from his parents. “There was much calmness and kindness among the Hefners, but little passion,” wrote Watts. Hefner, though, “chafed at even the mild restraints put in place by his parents.” His mother later confessed her parenting style came from advice she read in Parents magazine, which at the time recommended skimpy displays of affection and strict bedtimes and noted that kisses on the mouth should be avoided because that could spread germs.

Hefner was non-athletic and introverted but incredibly imaginative, and he immersed himself in movies, music, radio, cartoons and a love for animals. At about age 6, he allowed his dog to sleep on his beloved “bunny blanket” — which was replete with images of rabbits — and when the pet died, the parents burned the blanket, an experience Watts says may have influenced Hefner’s choice of a bunny for the logo of his empire years later.

When he was 9, Hefner published his first newspaper, which he sold to neighbors, and he created a couple more publications for his grammar school. When a fourth-grade teacher complained to his parents that he spent far too much class time drawing cartoons, he apologized for his transgression via a poem: “I will not make my teacher mad; Because that would make me sad; I will not draw at all in school; And I won’t brake [sic] a single rule.”

Read more: Hugh Hefner Backs Gay Marriage in Playboy Editorial

  As a teenager, Hefner read Edgar Allan Poe, H.G. Wells and Arthur Conan Doyle, according to Watts. He created a secret organization he called “The Shudder Club” for those who shared his passion for horror and science fiction, and he published five issues of Shudder magazine. “The boys were delighted when Bela Lugosi, Boris Karloff and Peter Lorre replied to their solicitation and accepted honorary positions in the club,” Watts wrote. He also started a newspaper in high school and took an interest in theater, starring is several plays.

A “dramatic change” in Hefner’s life occurred in the summer before his junior year when he crushed hard on a girl. The two took up dancing, but when she invited someone else to a hayride, it prompted him to make “a personal overhaul,” according to Watts. He transformed himself into a “Sinatra-like guy” with loud shirts and hip language, and he honed his dancing skills and began referring to himself as “Hef.” Soon, he and his friend Jim Brophy were the most popular kids at Steinmetz High School, and it was around this time that Hefner’s attraction to the opposite sex “veered close to obsession.”

He joined the U.S. Army in 1944 and was assigned a desk job at various places stateside. He drew cartoons for Army newspapers and attended dances and movies regularly. He was honorably discharged as a corporal in 1946 and returned to Chicago and enrolled at the University of Illinois, where his cartoons took on sexual themes. In 1947, he earned a pilot’s license.

When he became managing editor of the college's humor magazine, Shaft, he introduced a feature called “Coed of the Month,” an obvious precursor to the "Playboy Playmate of the Month.” He read Alfred Kinsey’s Sexual Behavior in the Human Male, published in 1948, and it “electrified” him, Watts wrote. Years later, Hefner’s college friends would recall marveling at how openly he spoke about matters pertaining to sex.

Despite complaints later in life that his dad wasn’t affectionate and his mom was overly Victorian, Hefner wrote in college: “Had I the ability to choose two perfect people for my parents, I don’t think I could have found a pair better for me than God did.”

After graduating, he failed to sell comic strips for newspaper syndication, then enrolled at Northwestern with the plan of becoming a college professor. He quit after a year and had a series of unfulfilling jobs at various magazines, including Esquire for $60 a week, which he quit when he didn’t get the $5 raise he sought. In 1952, he joined Publisher’s Development Corp., which put out small magazines with nude photography, and a year later he was making $120 a week at a children’s magazine. He found success on a local level in 1951 with the publication of his book of cartoons called That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals. The front cover was the sketch of a stripper.

He married a classmate, Millie Williams, in 1949, but “the troubled marriage faced growing pressure from Hugh’s increasingly active sexual imagination,” Watts wrote. The couple hosted risque parties that included stag films. Hefner began suggesting wife swapping, and he eventually slept with his brother’s wife, though Millie backed out of sex with Keith. They had a daughter, Christie, in 1952 and a son, David, in 1955, before divorcing in 1959.

Hefner set out to create his media empire at a particularly low point in his life in 1953 when he was despondent over a marriage he knew wasn’t working and a career that had stalled. He recalled in 2004 that he stood on a bridge in Chicago in the dead of winter thinking, “I’ve gotta do something.” That year, the first issue of Playboy was published.

In 1989, Hefner married Kimberly Conrad, a former Playmate of the Year, and the couple had sons Marston and Cooper. They divorced in 2010, and Hefner married Crystal Harris two years later.

In 2011, Hefner told The New York Times that he had already chosen and paid for his final resting place — a crypt next to Monroe’s in Westwood.

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