Playboy magazine founder Hugh Hefner dead aged 91

HUGH Hefner, founder of the iconic Playboy magazine, has died aged 91.

According to a statement from Playboy Enterprises, Hefner died of natural causes at his home in the Playboy Mansion.

Founding the magazine in 1953, Hefner built a brand that defined the sexual culture of the second half of the 20th century.

Playboy’s buxom models were the objects of millions of men’s fantasies as Hefner challenged what he derided as America’s “puritanical” attitudes toward sex. For decades, he was the pipe-smoking, silk-pyjama-wearing centre of a constant fantasy party at Playboy mansions in Chicago and then in Los Angeles. Hefner’s funeral or burial plans are unclear, but reports suggest his final resting place may be next to Marilyn Monroe. He bought the crypt next to her at the Westwood Village Memorial Park in Los Angeles nearly 25 years ago for almost $US100,000 ($A128,000) according to The Guardian.MORE: Inside Hugh Hefner’s Playboy mansionRENDEZVIEW: How Hugh Hefner changed the world

He famously only wore pyjamas at the Playboy Mansion, usually a black-lined red velour smoking jacket and a pair of silk PJs, teamed with black slippers.

So iconic was the look that it inspired dress-up costumes.

He also starred in the E! reality TV series The Girls Next Door.

Hefner is survived by his wife, Crystal, and four grown children: Christie, who served as CEO of Playboy Enterprise for more than 20 years, David, Marston and Cooper, who serves as chief creative officer at the company.

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” Cooper Hefner said in a statement.

“He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognisable and enduring in history. He will be greatly missed by many.”

Watch the video below for a peek into the Playboy Mansion, guided by Hefner’s son Cooper.

In his last posts to social media, Hefner encouraged his followers to donate to the One America Appeal to support hurricane victims of Harvey and Irma.

“My thoughts are with everyone affected by Hurricanes Harvey & Irma, both the victims and the first responders,” he wrote.

“... In times of such great adversity, it is inspiring to know we can put our differences aside and join together to help those in need ...

Playboy founder Hugh Hefner (centre) arrives at Stansted Airport on June 2, 2011 in Stansted, England to mark the launch of the new Playboy Club in Mayfair. Famous Bunnies have included Debbie Harry and Lauren Hutton. Picture: Getty1 of 37

Playboy founder Hugh Hefner is photographed at the Playboy Mansion in the Holmby Hills area of Los Angeles on Nov 17 2005. Playboy magazine founder and sexual revolution symbol Hugh Hefner has died at age 91. Picture: Getty2 of 37

Playboy Magazine publisher Hugh Hefner working in magazine office in Chicago, Illinois in 1960.3 of 37

Hugh Hefner poses at the Playboy Mansion in Los Angeles on Thursday April 5,2007. Picture: AP4 of 37

Playboy Enterprises founder and president Hugh Hefner gets a kiss from his girlfriend Barbara Benton under the tail of his 'Big Bunny' aircraft, 20/07/1970. Pic Keystone.5 of 37

Hugh Hefner and Pamela Anderson during Playboy’s 50th Anniversary Celebration in New York City - Inside at New York Armory in New York City, New York, United States. Picture: Getty6 of 37

American magazine publisher, founder and Chief Creative Officer of Playboy Enterprises, Hugh Hefner poses for a photograph at his home at the Playboy Mansion in Beverly Hills, Calif. Oct. 13, 2011 Picture: AP7 of 37

Playboy magazine founder and president Hugh Hefner with some of his bunnies at the Playboy Club, from the TV show 'America in The Fifties'.8 of 37

Hugh Hefner poses at Playboy’s 60th Anniversary special event on January 16, 2014 in Los Angeles, California. Picture: Getty Images for Playboy9 of 37

Publisher Hugh Hefner and girlfriend Holly Madison flash outside The Standard Hotel on September 24, 2003. Picture: Getty10 of 37

26th June 1966: Millionaire Hugh Hefner, founder of the Playboy empire, during a visit to Britain. Picture: Getty11 of 37

Hugh Hefner and Crystal Hefner attend Playboy Mansion’s Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. Picture: Getty for Playboy12 of 37

Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. Picture: Getty13 of 37

Hugh Hefner poses with Nicky and Paris Hilton during Playboy’s annual Halloween party in Los Angeles, 27/10/2007. Picture: Playboy14 of 37

Hugh Hefner during The Palms Casino Celebrates Playboy’s 50th Anniversary With Private Reception At Ghost Bar at The Palms Casino Resort in Las Vegas, Nevada. Picture: Getty15 of 37

Anna Nicole Smith with Hugh Hefner16 of 37

Playboy Magazine founder Hugh Hefner holding the first issue of Playboy featuring actress Marilyn Monroe on the cover. December 1953. Picture: Playboy17 of 37

Miss September Olivia Paige, Miss January Anna, Sheridyn Fisher, Hugh Hefner and girlfriend Crystal Harris. 27/06/201018 of 37

Hugh Hefner poses at the Playboy Mansion in Los Angeles on Thursday April 5,2007. Picture; AP19 of 37

Magazine publisher Hugh Hefner with girlfriends Holly Madison, Kendra Wilkinson and Bridget Marquardt in scene from TV program “Girls of the Playboy Mansion” Picture: Channel 920 of 37

Hugh Hefner and model Crystal Hefner attend the annual Halloween Party, hosted by Playboy and Hugh Hefner, at the Playboy Mansion on October 24, 2015 in Los Angeles, California. Getty Images for Playboy21 of 37

Hugh Hefner and girls of the Playboy Mansion. Holly Madison, Bridget Marquardt and Kendra Wilkinson.22 of 37

Head of Playboy Enterprises Hugh Hefner with wife Kimberley Conrad23 of 37

08/04/2006. In this photo released by Playboy, Playboy founder Hugh Hefner, poses with Paris Hilton as he celebrates his 80th birthday at the Playboy Mansion in the Holmby Hills area of Los Angeles. (AP Photo/Playboy, James Trevenen)24 of 37

Playboy magazine founder Hugh Hefner with Playboy models, Holly Madison in scene from TV programme “Girls of a Playboy Mansion”.25 of 37

Playboy Editor-in-Chief and CEO Hugh Hefner at the Playboy Mansion in Los Angeles, California 05/04/07.26 of 37

Dita Von Teese and Playboy founder Hugh Hefner attend the Playboy party at Barfly on November 15, 2002 in West Hollywood, California. Von Teese is featured as Miss December 2002 for Playboy’s holiday issue. Picture: Getty27 of 37

Playmate Holly Madison, publisher Hugh Hefner, playmate Bridget Marquardt and playmate Kendra Wilkinson arrive at Columbia Pictures’ premiere of “House Bunny” held at the Mann Village Theater on August 20, 2008 in Westwood, California. Picture: Getty28 of 37

Rod Stewart poses with Playboy founder Hugh Hefner at The Pharmacy on October 9, 2002 in Hollywood, California. Picture: Getty29 of 37

Playboy publisher Hugh Hefner (c) celebrating Playboy’s 50th anniversary at Palms hotel in Las Vegas 20 Sep 2003.30 of 37

Playboy Magazine founder Hugh Hefner attends the world premiere of Iron Man 2 at the El Capitan Theater n the Hollywood section of Los Angeles on April 26, 2010. . Picture: AFP31 of 37

Publisher Hugh Hefner arrives with Girls Next Door Kendra Wilkinson, Holly Madison and Bridget Marquardt at the 36th AFI Life Achievement Award tribute to Warren Beatty held at the Kodak Theatre on June 11, 2008 in Hollywood, California. Picture: Getty32 of 37

‘Playboy’ magazine founder Hugh Hefner (L) and ‘The Girls Next Door’ reality series star Holly Madison attend a signing of ‘Playboy Cover to Cover: The 50s’ at Barnes & Noble Booksellers at The Grove on November 15, 2007 in Los Angeles, California. Picture: Getty33 of 37

James Caan and Hugh Hefner have a laugh during Fight Night at the Playboy Mansion on July 15, 2003 in Bel Air, California. Picture: Getty34 of 37

Hugh Hefner and girls of the Playboy Mansion. Holly Madison, Bridget Marquardt and Kendra Wilkinson.35 of 37

April 7, 2006, Playboy founder Hugh Hefner is photographed at the Playboy Mansion in the Holmby Hills area of Los Angeles. Picture: AP36 of 37

Kiss bassist Gene Simmons poses with Playboy founder, Hugh Hefner during the Tongue Magazine Fall 2002 Issue release party at Barfly on September 27, 2002 in West Hollywood, California. Picture: Getty37 of 37

Playboy founder Hugh Hefner (centre) arrives at Stansted Airport on June 2, 2011 in Stansted, England to mark the launch of the new Playboy Club in Mayfair. Famous Bunnies have included Debbie Harry and Lauren Hutton. Picture: Getty

Playboy founder Hugh Hefner is photographed at the Playboy Mansion in the Holmby Hills area of Los Angeles on Nov 17 2005. Playboy magazine founder and sexual revolution symbol Hugh Hefner has died at age 91. Picture: Getty

Playboy Magazine publisher Hugh Hefner working in magazine office in Chicago, Illinois in 1960.

Hugh Hefner poses at the Playboy Mansion in Los Angeles on Thursday April 5,2007. Picture: AP

Playboy Enterprises founder and president Hugh Hefner gets a kiss from his girlfriend Barbara Benton under the tail of his 'Big Bunny' aircraft, 20/07/1970. Pic Keystone.

Hugh Hefner and Pamela Anderson during Playboy’s 50th Anniversary Celebration in New York City - Inside at New York Armory in New York City, New York, United States. Picture: Getty

American magazine publisher, founder and Chief Creative Officer of Playboy Enterprises, Hugh Hefner poses for a photograph at his home at the Playboy Mansion in Beverly Hills, Calif. Oct. 13, 2011 Picture: AP

Playboy magazine founder and president Hugh Hefner with some of his bunnies at the Playboy Club, from the TV show 'America in The Fifties'.

Hugh Hefner poses at Playboy’s 60th Anniversary special event on January 16, 2014 in Los Angeles, California. Picture: Getty Images for Playboy

Publisher Hugh Hefner and girlfriend Holly Madison flash outside The Standard Hotel on September 24, 2003. Picture: Getty

26th June 1966: Millionaire Hugh Hefner, founder of the Playboy empire, during a visit to Britain. Picture: Getty

Hugh Hefner and Crystal Hefner attend Playboy Mansion’s Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. Picture: Getty for Playboy

Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. Picture: Getty

Hugh Hefner poses with Nicky and Paris Hilton during Playboy’s annual Halloween party in Los Angeles, 27/10/2007. Picture: Playboy

Hugh Hefner during The Palms Casino Celebrates Playboy’s 50th Anniversary With Private Reception At Ghost Bar at The Palms Casino Resort in Las Vegas, Nevada. Picture: Getty

Anna Nicole Smith with Hugh Hefner

Playboy Magazine founder Hugh Hefner holding the first issue of Playboy featuring actress Marilyn Monroe on the cover. December 1953. Picture: Playboy

Miss September Olivia Paige, Miss January Anna, Sheridyn Fisher, Hugh Hefner and girlfriend Crystal Harris. 27/06/2010

Hugh Hefner poses at the Playboy Mansion in Los Angeles on Thursday April 5,2007. Picture; AP

Magazine publisher Hugh Hefner with girlfriends Holly Madison, Kendra Wilkinson and Bridget Marquardt in scene from TV program “Girls of the Playboy Mansion” Picture: Channel 9

Hugh Hefner and model Crystal Hefner attend the annual Halloween Party, hosted by Playboy and Hugh Hefner, at the Playboy Mansion on October 24, 2015 in Los Angeles, California. Getty Images for Playboy

Hugh Hefner and girls of the Playboy Mansion. Holly Madison, Bridget Marquardt and Kendra Wilkinson.

Head of Playboy Enterprises Hugh Hefner with wife Kimberley Conrad

08/04/2006. In this photo released by Playboy, Playboy founder Hugh Hefner, poses with Paris Hilton as he celebrates his 80th birthday at the Playboy Mansion in the Holmby Hills area of Los Angeles. (AP Photo/Playboy, James Trevenen)

Playboy magazine founder Hugh Hefner with Playboy models, Holly Madison in scene from TV programme “Girls of a Playboy Mansion”.

Playboy Editor-in-Chief and CEO Hugh Hefner at the Playboy Mansion in Los Angeles, California 05/04/07.

Dita Von Teese and Playboy founder Hugh Hefner attend the Playboy party at Barfly on November 15, 2002 in West Hollywood, California. Von Teese is featured as Miss December 2002 for Playboy’s holiday issue. Picture: Getty

Playmate Holly Madison, publisher Hugh Hefner, playmate Bridget Marquardt and playmate Kendra Wilkinson arrive at Columbia Pictures’ premiere of “House Bunny” held at the Mann Village Theater on August 20, 2008 in Westwood, California. Picture: Getty

Rod Stewart poses with Playboy founder Hugh Hefner at The Pharmacy on October 9, 2002 in Hollywood, California. Picture: Getty

Playboy publisher Hugh Hefner (c) celebrating Playboy’s 50th anniversary at Palms hotel in Las Vegas 20 Sep 2003.

Playboy Magazine founder Hugh Hefner attends the world premiere of Iron Man 2 at the El Capitan Theater n the Hollywood section of Los Angeles on April 26, 2010. . Picture: AFP

Publisher Hugh Hefner arrives with Girls Next Door Kendra Wilkinson, Holly Madison and Bridget Marquardt at the 36th AFI Life Achievement Award tribute to Warren Beatty held at the Kodak Theatre on June 11, 2008 in Hollywood, California. Picture: Getty

‘Playboy’ magazine founder Hugh Hefner (L) and ‘The Girls Next Door’ reality series star Holly Madison attend a signing of ‘Playboy Cover to Cover: The 50s’ at Barnes & Noble Booksellers at The Grove on November 15, 2007 in Los Angeles, California. Picture: Getty

James Caan and Hugh Hefner have a laugh during Fight Night at the Playboy Mansion on July 15, 2003 in Bel Air, California. Picture: Getty

Hugh Hefner and girls of the Playboy Mansion. Holly Madison, Bridget Marquardt and Kendra Wilkinson.

April 7, 2006, Playboy founder Hugh Hefner is photographed at the Playboy Mansion in the Holmby Hills area of Los Angeles. Picture: AP

Kiss bassist Gene Simmons poses with Playboy founder, Hugh Hefner during the Tongue Magazine Fall 2002 Issue release party at Barfly on September 27, 2002 in West Hollywood, California. Picture: Getty

HIDE THUMBS

Hefner was no stranger to controversy.

He was avidly involved in civil rights activism, battled censorship in the courts and constantly sparred with the likes of the FBI and DEA.

But his greatest victory was the obscenity battles of the 1960s.

Hefner was arrested for “publishing and distributing an obscene magazine” on June 4th, 1963 on a warrant issued by Judge Norman N. Eiger.

The courtroom struggle centred on who got to decide what was obscenity, and what was acceptable.

The case was declared a mistrial when the jury deadlocked 7 to 5.

Scandal was never far from Hefner. He fled Chicago in 1975 amid a grand jury investigation into drug activities at his home and the drug-related death of one of his secretaries and a Playboy club bunny.

In 2005, British twins Carla and Melissa Howe spilt the beans on what life in an ageing Hefner’s Playboy Mansion was like as his soft-porn empire collapsed around him.

Instead of a sex demon, Hefner behaved more like an overly protective grandfather who imposed curfews on ‘his girls’, they said.

“When you’re here you have to be in by the 9pm curfew. You’re not allowed to invite any friends up to see you. You’re definitely not allowed male visitors. If you break the rules you get banned. Once you’re out, you’re out, you can’t come back,” Carla said.

As for his later-life sex drive: “I’m really relieved … we’ve heard stories about him having 16 girls in the grotto and once he’d finished they would be passed on to the next man there.”

But former Playmate Kendra Wilkinson recently told how she had to get “very drunk and very stoned” to endure sex sessions with the then octogenarian tycoon.

In another scandal, glamour model Chloe Goins boldly accused Hugh Hefner of allowing Bill Cosby to unknowingly drug underage women during several of his Playboy Mansion parties. The Playboy founder responded by saying he had no knowledge of or involvement in Cosby’s alleged behaviour at the Mansion and that her claims were unfounded. The LAPD has since decided to not go forward with criminal charges against Hugh Hefner.

EARLY LIFE

Hefner was born on April 9, 1926 in Chicago, Illinois, to teacher parents Grace Caroline and Glenn Lucius Hefner. From a young age he demonstrated an interest in writing and drawing (particularly cartoons). He founded a school paper and was president of the student council.

Marilyn Monroe on the first cover of Playboy magazine, December 1953. Picture: Playboy1 of 43

Anna Nicole Smith on the cover of Playboy magazine, February 1994. Picture: Playboy2 of 43

Elle Macpherson on the cover of Playboy magazine, May 1994. Picture: Playboy3 of 43

Pamela Anderson on the cover of Playboy magazine, May 2004. Picture: Playboy4 of 43

Donald Trump and Brandi Brandt on the cover of Playboy magazine, March 1990. Picture: Playboy5 of 43

Kim Kardashian on the cover of Playboy magazine, December 2007. Picture: Playboy6 of 43

Bo Derek on the cover of Playboy magazine, March 1980. Picture: Playboy7 of 43

Kate Moss on the cover of Playboy magazine, January/February 2014. Picture: Playboy8 of 43

Drew Barrymore on the cover of Playboy magazine, January 1995. Picture: Playboy9 of 43

Cindy Crawford on the cover of Playboy magazine, October 1998. Picture: Playboy10 of 43

Mariah Carey on the cover of Playboy magazine, March 2007. Picture: Playboy11 of 43

Marilyn Monroe on the cover of Playboy magazine, December 2005. Picture: Playboy12 of 43

Lindsay Lohan on the cover of Playboy magazine, January/February 2012. Picture: Playboy13 of 43

Goldie Hawn on the cover of Playboy magazine, January 1985. Picture: Playboy14 of 43

Dolly Parton on the cover of Playboy magazine, October 1978. Picture: Playboy15 of 43

Madonna on the cover of Playboy magazine, September 1985. Picture: Playboy16 of 43

Paris Hilton on the cover of Playboy magazine, March 2005. Picture: Playboy17 of 43

Steve Martin, Amy Miller and Michele Drake on the cover of Playboy magazine, January 1980. Picture: Playboy18 of 43

Raquel Welch on the cover of Playboy magazine, December 1979. Picture: Playboy19 of 43

Sharon Stone on the cover of Playboy magazine, July 1990. Picture: Playboy20 of 43

Naomi Campbell on the cover of Playboy magazine, December 1999. Picture: Playboy21 of 43

Jessica Alba on the cover of Playboy magazine, March 2006. Picture: Playboy22 of 43

Charlize Theron on the cover of Playboy magazine, May 1999. Picture: Playboy23 of 43

Claudia Schiffer on the cover of Playboy magazine, May 1997. Picture: Playboy24 of 43

Geri Halliwell on the cover of Playboy magazine, May 1998. Picture: Playboy25 of 43

Brooke Shields on the cover of Playboy magazine, December 1986. Picture: Playboy26 of 43

Anna Faris on the cover of Playboy magazine, September 2008. Picture: Playboy27 of 43

Barbara Streisand on the cover of Playboy magazine, October 1977. Picture: Playboy28 of 43

Chelsea Handler on the cover of Playboy magazine, December 2009 double issue. Picture: Playboy29 of 43

Farrah Fawcett on the cover of Playboy magazine, July 1997. Picture: Playboy30 of 43

Jerry Seinfeld, Echo Johnson, Barbara Moore, Kimberly Donley, Suzi Simpson, Carrie Westcott, Tylyn John, Cheryl Bachman and Alex Philip on the cover of Playboy magazine, October 1993. Picture: Playboy31 of 43

Joan Collins on the cover of Playboy magazine, December 1983. Picture: Playboy32 of 43

Gene Simmons on the cover of Playboy magazine, March 1999. Picture: Playboy33 of 43

Sally Field on the cover of Playboy magazine, March 1986. Picture: Playboy34 of 43

Rachel Hunter on the cover of Playboy magazine, April 2004. Picture: Playboy35 of 43

Tara Reid on the cover of Playboy magazine, January/February 2010. Picture: Playboy36 of 43

Carmen Electra on the cover of Playboy magazine, April 2003. Picture: Playboy37 of 43

Dita Von Teese on the cover of Playboy magazine, December 2002. Picture: Playboy38 of 43

La Toya Jackson on the cover of Playboy magazine, November 1991. Picture: Playboy39 of 43

Jenny McCarthy on the cover of Playboy magazine, January 2005. Picture: Playboy40 of 43

Seth Rogan and Hope Dworaczyk on the cover of Playboy magazine, April 2009. Picture: Playboy41 of 43

Daryl Hannah on the cover of Playboy magazine, November 2003. Picture: Playboy42 of 43

Bruno Mars and Raquel Pomplun on the cover of Playboy magazine, April 2012. Picture: Playboy43 of 43

Marilyn Monroe on the first cover of Playboy magazine, December 1953. Picture: Playboy

Anna Nicole Smith on the cover of Playboy magazine, February 1994. Picture: Playboy

Elle Macpherson on the cover of Playboy magazine, May 1994. Picture: Playboy

Pamela Anderson on the cover of Playboy magazine, May 2004. Picture: Playboy

Donald Trump and Brandi Brandt on the cover of Playboy magazine, March 1990. Picture: Playboy

Kim Kardashian on the cover of Playboy magazine, December 2007. Picture: Playboy

Bo Derek on the cover of Playboy magazine, March 1980. Picture: Playboy

Kate Moss on the cover of Playboy magazine, January/February 2014. Picture: Playboy

Drew Barrymore on the cover of Playboy magazine, January 1995. Picture: Playboy

Cindy Crawford on the cover of Playboy magazine, October 1998. Picture: Playboy

Mariah Carey on the cover of Playboy magazine, March 2007. Picture: Playboy

Marilyn Monroe on the cover of Playboy magazine, December 2005. Picture: Playboy

Lindsay Lohan on the cover of Playboy magazine, January/February 2012. Picture: Playboy

Goldie Hawn on the cover of Playboy magazine, January 1985. Picture: Playboy

Dolly Parton on the cover of Playboy magazine, October 1978. Picture: Playboy

Madonna on the cover of Playboy magazine, September 1985. Picture: Playboy

Paris Hilton on the cover of Playboy magazine, March 2005. Picture: Playboy

Steve Martin, Amy Miller and Michele Drake on the cover of Playboy magazine, January 1980. Picture: Playboy

Raquel Welch on the cover of Playboy magazine, December 1979. Picture: Playboy

Sharon Stone on the cover of Playboy magazine, July 1990. Picture: Playboy

Naomi Campbell on the cover of Playboy magazine, December 1999. Picture: Playboy

Jessica Alba on the cover of Playboy magazine, March 2006. Picture: Playboy

Charlize Theron on the cover of Playboy magazine, May 1999. Picture: Playboy

Claudia Schiffer on the cover of Playboy magazine, May 1997. Picture: Playboy

Geri Halliwell on the cover of Playboy magazine, May 1998. Picture: Playboy

Brooke Shields on the cover of Playboy magazine, December 1986. Picture: Playboy

Anna Faris on the cover of Playboy magazine, September 2008. Picture: Playboy

Barbara Streisand on the cover of Playboy magazine, October 1977. Picture: Playboy

Chelsea Handler on the cover of Playboy magazine, December 2009 double issue. Picture: Playboy

Farrah Fawcett on the cover of Playboy magazine, July 1997. Picture: Playboy

Jerry Seinfeld, Echo Johnson, Barbara Moore, Kimberly Donley, Suzi Simpson, Carrie Westcott, Tylyn John, Cheryl Bachman and Alex Philip on the cover of Playboy magazine, October 1993. Picture: Playboy

Joan Collins on the cover of Playboy magazine, December 1983. Picture: Playboy

Gene Simmons on the cover of Playboy magazine, March 1999. Picture: Playboy

Sally Field on the cover of Playboy magazine, March 1986. Picture: Playboy

Rachel Hunter on the cover of Playboy magazine, April 2004. Picture: Playboy

Tara Reid on the cover of Playboy magazine, January/February 2010. Picture: Playboy

Carmen Electra on the cover of Playboy magazine, April 2003. Picture: Playboy

Dita Von Teese on the cover of Playboy magazine, December 2002. Picture: Playboy

La Toya Jackson on the cover of Playboy magazine, November 1991. Picture: Playboy

Jenny McCarthy on the cover of Playboy magazine, January 2005. Picture: Playboy

Seth Rogan and Hope Dworaczyk on the cover of Playboy magazine, April 2009. Picture: Playboy

Daryl Hannah on the cover of Playboy magazine, November 2003. Picture: Playboy

Bruno Mars and Raquel Pomplun on the cover of Playboy magazine, April 2012. Picture: Playboy

HIDE THUMBS

MARRIED WITH CHILDRENHefner married his college sweetheart Mildred Williams in 1949, but just before their wedding, Mildred admitted she had had an affair while he was serving in the army — a confession Hefner later described as “the most devastating moment of my life”. As a result of her own infidelity, Mildred would turn a blind eye to Hefner’s many liaisons. The pair had two children — Christie and David Hefner — before divorcing after 10 years of marriage.

He continued his playboy lifestyle until 1989, when he tied the knot with Playmate of the year Kimberly Conrad (they divorced in 2010).

He married another Playmate, Crystal Harris, in 2012, and remained with her until his death.

PLAYBOY MAGAZINE In December 1953, a year after he quit his job at Esquire, he launched Playboy magazine, using money raised from 45 investors (including $1,000 from his mother) and a bank loan. The first issue, which he produced in his own home, featured a nude image of Marilyn Monroe as a centrefold — it was an instant hit, selling a staggering 50,000 copies. Because Hefner wasn’t sure how successful the magazine would be, the first issue was undated.

The iconic Playboy logo of a rabbit wearing a bow tie first appeared in the second issue of the magazine. Hefner later said that the rabbit was selected for its “humorous sexual connotation”.

A common joke among Playboy’s readers was that they only read it “for the articles”, but in fact the magazine was noted for publishing some of the greatest writers of the 20th century.

Authors who had original stories and journalism published in Playboy included Jack Kerouac, Kurt Vonnegut, Gabriel Garcia Marquez, Roald Dahl and Ian Fleming.

Feminist authors Joyce Carol Oates and Margaret Atwood also had stories published in the magazine. The magazine’s highest-selling issue was the November 1972 edition - it sold over 7,000,000 copies.

LOVE LIFE

Hefner’s romantic life has long made headlines — he was into peroxide blondes, and dated many women at the same time.

Perhaps most famously was his three-way relationship with Kendra Wilkinson, Bridget Marquardt, and Holly Madison who starred on his E! reality series, Girls of the Playboy Mansion.

Though not one to give up his polyamory, Hefner tied the knot with Crystal Harris in 2012 — he was 86 and she was 26.

He also dated Baywatch actor Brande Roderick, twins Kristina and Karissa Shannon and Polish playmate Izabella St. James.

Madison revealed the dark side to her relationship with Hefner in her 2016 memoir, The Vegas Diaries.

“All of those people who watched The Girls Next Door … They thought I was happy with Hef.

“Hef painted it like it was some sort of fairytale.”

She described the mansion as a “farce with this vicious horde of girls”, and accused Hefner of controlling and verbally abusive behaviour.

“He liked to play favorites to keep everyone on their toes. How else could he stay in control of seven women? He needed to somehow maintain the upper hand.”

ICON REMEMBERED

Tributes have started flowing for the magazine icon.

Neil Strauss, author of The Game, has Tweeted:

American actor Kat Dennings wrote: “I met Hugh Hefner at the Playboy mansion. He was very nice to my mom. Don’t ask.”

American porn star Ron Jeremy wrote: “#RestInPeace Hugh Hefner. Charing Cross Road will never be the same. #HughHefner”

Kim Kardashian tweeted: “I’m honored to have been a part of the Playboy team! You’ll be greatly missed! Love you Hef! xoxo”

Paris Hilton responded to Hefner’s passing with an emoji.

Parks and Recreation star Rob Lowe called Hefner a “true legend”.

Nancy Sinatra said the Playboy founder was “one of the nicest men I’ve ever known”.

Larry King paid tribute to his friend saying he was “a giant in publishing, journalism, free speech and civil rights”.

Oscar-winning actor Marlee Matlin fondly remembered the “publishing giant”.

TV host Ryan Seacrest said the Hollywood legend “lived life to the fullest”.

Australian model Simone Holtznagel posted a picture of her Playboy cover with the message to “rest well in the bosoms of ... heaven”.