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==Career== In January 1952, Hefner left his job as a copywriter for ''[[Esquire (magazine)|Esquire]]'' after he was denied a $5 raise. In 1953, he took out a mortgage loan of $600 and raised $8,000 from 45 investors (including $1,000 from his motherβ"not because she believed in the venture," he told ''[[E!]]'' in 2006, "but because she believed in her son") to launch ''[[Playboy]]'', which was initially going to be called ''Stag Party''. The first issue was published in December 1953 and featured [[Marilyn Monroe]] from a 1949 nude calendar shoot she did under a pseudonym.<ref>{{Cite web|title=Marilyn Monroe Didn't Actually Pose for the First Issue of Playboy|url=https://www.biography.com/news/marilyn-monroe-playboy-first-issue-didnt-pose|last=Witter|first=Brad|website=Biography|language=en-us|access-date=May 22, 2020|archive-date=February 19, 2020|archive-url=https://web.archive.org/web/20200219232306/https://www.biography.com/news/marilyn-monroe-playboy-first-issue-didnt-pose|url-status=live}}</ref> That first issue sold more than 50,000 copies, but Monroe was not paid by Playboy or Hefner for the photos.<ref>[http://entrepreneurs.about.com/od/famousentrepreneurs/p/hughhefner.htm Hugh Hefner: The Ultimate Lifestyle Entrepreneur] {{Webarchive|url=https://web.archive.org/web/20051018200611/http://entrepreneurs.about.com/od/famousentrepreneurs/p/hughhefner.htm |date=October 18, 2005 }}. Entrepreneurs.about.com. Retrieved on May 3, 2012.</ref><ref name=wapo-monroe>{{cite web|url=https://www.washingtonpost.com/news/arts-and-entertainment/wp/2017/09/28/marilyn-monroe-helped-launch-hugh-hefners-career-but-they-never-even-met/|title=Marilyn Monroe helped launch Hugh Hefner's career. But they never even met.|work=[[washingtonpost.com]]|access-date=Dec 27, 2022|archive-date=May 27, 2022|archive-url=https://web.archive.org/web/20220527053320/https://www.washingtonpost.com/news/arts-and-entertainment/wp/2017/09/28/marilyn-monroe-helped-launch-hugh-hefners-career-but-they-never-even-met/|url-status=live}}</ref> (Hefner never met Monroe, but he bought the crypt next to hers at the [[Westwood Village Memorial Park Cemetery]] in 1992 for $75,000.)<ref name="NYT_20110203">{{cite news | url = https://www.nytimes.com/2011/02/06/magazine/06Hefner-t.html | title = How Hef Got His Groove Back | date = February 3, 2011 | author = Charles McGrath | work = The New York Times | access-date = February 24, 2017 | archive-date = January 25, 2017 | archive-url = https://web.archive.org/web/20170125113341/http://www.nytimes.com/2011/02/06/magazine/06Hefner-t.html | url-status = live }}</ref><ref>[http://www.seeing-stars.com/Buried2/PierceBros5.shtml Westwood Village Memorial Cemetery] {{Webarchive|url=https://web.archive.org/web/20070929095703/http://www.seeing-stars.com/Buried2/PierceBros5.shtml |date=September 29, 2007 }}. Seeing-Stars.com.</ref> ''[[Esquire (magazine)|Esquire]]'' magazine rejected [[Charles Beaumont]]'s science fiction story "The Crooked Man" in 1955, so Hefner agreed to publish it in ''Playboy.'' The story highlighted straight men being persecuted in a world where homosexuality was the norm. The magazine received angry letters, so Hefner responded, "If it was wrong to persecute heterosexuals in a homosexual society then the reverse was wrong, too."<ref>[http://www.advocate.com/news/daily-news/2009/08/28/hugh-hefner-gay-rights-pioneer "Hugh Hefner, Gay Rights Pioneer"] {{Webarchive|url=https://web.archive.org/web/20120529011523/http://www.advocate.com/news/daily-news/2009/08/28/hugh-hefner-gay-rights-pioneer |date=May 29, 2012 }}, advocate.com</ref> In 1961, Hefner watched [[Dick Gregory]] perform at the Herman Roberts Show Bar in Chicago, and he hired Gregory to work at the Chicago Playboy Club. Gregory attributed the launch of his career to that night.<ref>{{cite news|url=http://www.chicagotribune.com/news/opinion/page/ct-perspec-page-dick-gregory-civil-rights-0823-story.html|title=Column: Dick Gregory understood the political power of comedy|newspaper=Chicago Tribune|date=August 22, 2017|access-date=September 27, 2017|archive-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928145911/http://www.chicagotribune.com/news/opinion/page/ct-perspec-page-dick-gregory-civil-rights-0823-story.html|url-status=live}}</ref> Hefner promoted a ''bon vivant'' lifestyle in his magazine and in the television shows that he hosted, ''[[Playboy's Penthouse]]'' (1959β1960) and ''[[Playboy After Dark]]'' (1969β1970).<ref>{{cite web|url=https://www.biography.com/people/hugh-hefner-9333521|title=Hugh Hefner|website=Biography.com|access-date=November 7, 2017|archive-date=November 15, 2017|archive-url=https://web.archive.org/web/20171115200152/https://www.biography.com/people/hugh-hefner-9333521|url-status=live}}</ref> He was also the chief creative officer of [[Playboy Enterprises]], the publishing group which operates the magazine.<ref>[http://www.playboyenterprises.com/home/content.cfm?content=t_officers&ArtTypeID=CorpOfficers&MmenuFlag=profile&SmenuFlag=sub_corp_profile_officers_o Corporate Officers] {{Webarchive|url=https://web.archive.org/web/20150924074216/http://www.playboyenterprises.com/home/content.cfm?content=t_officers&ArtTypeID=CorpOfficers&MmenuFlag=profile&SmenuFlag=sub_corp_profile_officers_o |date=September 24, 2015 }}, Playboy Enterprises, Inc.</ref> On June 4, 1963, Hefner was arrested for promoting obscene literature after he published an issue of ''Playboy'' featuring nude shots of [[Jayne Mansfield]] in bed with a man present.<ref>{{cite book | last = Pitzulo | first = Carrie | title = Bachelors and Bunnies: The Sexual Politics of Playboy | publisher = University of Chicago Press | year = 2011 | page = [https://archive.org/details/bachelorsbunnies00pitz/page/66 66] | isbn = 978-0-226-67006-5 | url-access = registration | url = https://archive.org/details/bachelorsbunnies00pitz/page/66 }}</ref> The case went to trial and resulted in a [[hung jury]].<ref>[http://www.biography.com/articles/Hugh-Hefner-9333521?part=1 Hugh Hefner Biography] {{Webarchive|url=https://web.archive.org/web/20110613035146/http://www.biography.com/articles/Hugh-Hefner-9333521?part=1 |date=June 13, 2011 }}. biography.com.</ref> In the 1960s, Hefner created "private key" clubs that were racially diverse.<ref>{{cite web|url=https://www.biography.com/people/hugh-hefner-9333521|title=Hugh Hefner|website=Biography|language=en-us|access-date=April 30, 2018|archive-date=November 15, 2017|archive-url=https://web.archive.org/web/20171115200152/https://www.biography.com/people/hugh-hefner-9333521|url-status=live}}</ref> During the civil rights movement in 1966, Hefner sent [[Alex Haley]] to interview [[American Nazi Party]] founder [[George Lincoln Rockwell]], much to Rockwell's shock because Haley was black. Rockwell agreed to meet with Haley only after gaining assurance that he was not Jewish, although Rockwell kept a handgun on the table throughout the interview.<ref>{{cite news|last=Hearn|first=Michael Patrick|url=https://www.nytimes.com/2021/12/17/books/review/alex-haley-hamilton-college-autobiography-of-malcolm-x-roots.html|title=Alex Haley Taught America About Race β and a Young Man How to Write|work=The New York Times|date=December 17, 2021|access-date=January 25, 2022|archive-date=January 20, 2022|archive-url=https://web.archive.org/web/20220120081659/https://www.nytimes.com/2021/12/17/books/review/alex-haley-hamilton-college-autobiography-of-malcolm-x-roots.html|url-status=live}}</ref> In ''[[Roots: The Next Generations]]'' (1979), the interview was recreated with [[James Earl Jones]] as Haley and [[Marlon Brando]] as Rockwell.<ref>{{cite news|last=Maslin|first=Janet|url=https://www.nytimes.com/1979/02/25/archives/tv-end-of-roots-ii-delineates-60s.html|title=TV: End of 'Roots II' Delineates 60's|work=The New York Times|date=February 25, 1979|access-date=January 25, 2022|archive-date=January 27, 2022|archive-url=https://web.archive.org/web/20220127013509/https://www.nytimes.com/1979/02/25/archives/tv-end-of-roots-ii-delineates-60s.html|url-status=live}}</ref> Haley had also interviewed [[Malcolm X]] in 1963 and [[Martin Luther King Jr.]] in 1966 for the newly established 1962 "playboy interview".<ref>{{cite press release|title=American Icon and Playboy Founder, Hugh M. Hefner, Has Died|url=https://www.prnewswire.com/news-releases/american-icon-and-playboy-founder-hugh-m-hefner-has-died-300527267.html|publisher=PR Newswire|access-date=September 28, 2017|archive-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928032950/http://www.prnewswire.com/news-releases/american-icon-and-playboy-founder-hugh-m-hefner-has-died-300527267.html|url-status=live}}</ref> [[File:Hugh Hefner 1966.jpg|thumb|right|upright|Hefner with his trademark Playboy Pipe in 1966]] In 1970, Hefner stated that "militant feminists" are "unalterably opposed to the romantic boy-girl society that ''Playboy'' promotes" and ordered an article in his magazine against them.<ref name="Redden2017">{{cite news|url=https://www.theguardian.com/media/2017/sep/28/hugh-hefner-playboy-founder-91-dark-side|title=Effusive Hugh Hefner tributes ignore Playboy founder's dark side|last=Redden|first=Molly|date=September 29, 2017|newspaper=[[The Guardian]] |language=en|access-date=September 29, 2017|archive-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928230223/https://www.theguardian.com/media/2017/sep/28/hugh-hefner-playboy-founder-91-dark-side|url-status=live}}</ref> In his later years, Hefner's star dimmed, but he remained a well-known personality, often appearing in cameo roles. In the 1993 ''[[The Simpsons]]'' episode "[[Krusty Gets Kancelled]]", Hefner voiced himself.<ref>{{cite web |date=February 17, 2012 |title="The Simpsons" guests stars over the years |url=https://www.cbsnews.com/pictures/the-simpsons-guests-stars-over-the-years/3/ |url-status=live |archive-url=https://web.archive.org/web/20170929000402/https://www.cbsnews.com/pictures/the-simpsons-guests-stars-over-the-years/3/ |archive-date=September 29, 2017 |access-date=February 20, 2018 |website=[[CBS News]]}}</ref><ref name="playboy.com">{{cite web |date=April 8, 2016 |title=The Original Playboy: A Timeline of the Life and Accomplishments of Hugh M. Hefner |url=http://www.playboy.com/articles/hugh-hefner-timeline |url-status=live |archive-url=https://web.archive.org/web/20161019213026/http://www.playboy.com/articles/hugh-hefner-timeline |archive-date=October 19, 2016 |access-date=October 19, 2016}}</ref> In 1999, Hefner financed the [[Clara Bow]] documentary ''Discovering the It Girl''. "Nobody has what Clara had," he said. "She defined an era and made her mark on the nation".<ref>Variety, June 7, 1999</ref> Hefner guest-starred as himself in the 2000 ''[[Sex and the City]]'' episode "Sex and Another City".<ref name="PlayboyTV">{{cite magazine|url=https://ew.com/tv/2017/09/28/hugh-hefner-as-himself-5-times-the-playboy-founder-made-memorable-tv-cameos/|title=Playboy on TV: 5 memorable Hugh Hefner cameos|date=September 28, 2017|magazine=Entertainment Weekly|access-date=February 20, 2020|archive-date=December 30, 2019|archive-url=https://web.archive.org/web/20191230140802/https://ew.com/tv/2017/09/28/hugh-hefner-as-himself-5-times-the-playboy-founder-made-memorable-tv-cameos/|url-status=live}}</ref> In 2005, he guest-starred on the HBO shows ''[[Curb Your Enthusiasm]]'' and ''[[Entourage (U.S. TV series)|Entourage]]''.<ref name="PlayboyTV" /> He guest-starred as himself in a 2006 episode of [[Seth Green]]'s ''[[Robot Chicken]]'' on the late-night programming block [[Adult Swim]].<ref name="playboy.com" /> In the 2007 ''[[Family Guy]]'' episode "[[Airport '07]]", he voiced himself.<ref name="PlayboyTV" /> He has a star on the [[Hollywood Walk of Fame]] for television and made several movie appearances as himself. In 2009, he was nominated for a [[Golden Raspberry Award for Worst Supporting Actor]] for his performance as himself in ''[[Miss March]]''. On his official Twitter account, he joked about this nomination: "Maybe I didn't understand the character."<ref>{{cite web|url=https://twitter.com/hughhefner/status/8637804425|title=Hugh Hefner on Twitter|access-date=October 19, 2016|archive-date=March 5, 2016|archive-url=https://web.archive.org/web/20160305041355/https://twitter.com/hughhefner/status/8637804425|url-status=live}}</ref> Brigitte Berman's documentary ''[[Hugh Hefner: Playboy, Activist and Rebel]]'' was released on July 30, 2010. He had previously granted full access to documentary filmmaker and television producer [[Kevin Burns]] for the A&E ''[[Biography (TV series)|Biography]]'' special ''Hugh Hefner: American Playboy'' in 1996.<ref>[http://www.hughhefnerplayboyactivistrebel.com/ Hugh Hefner: Playboy, Activist and Rebel] {{Webarchive|url=https://web.archive.org/web/20210115195240/http://hughhefnerplayboyactivistrebel.com/ |date=January 15, 2021 }}. Hughhefnerplayboyactivistrebel.com (December 7, 2010). Retrieved on May 3, 2012.</ref> Hefner and Burns later collaborated on numerous other television projects, most notably on ''[[The Girls Next Door]]'', a reality series that ran for six seasons (2005β2009) and 90 episodes.<ref>{{cite web|url=https://www.msn.com/en-us/entertainment/celebrity/hugh-hefner-playboy-magazine-founder-and-star-of-girls-next-door-dies-at-91/ar-AAsyeDX?li=BBnbfcL|title=Hugh Hefner, Playboy Magazine Founder and Star of Girls Next Door, Dies at 91|publisher=MSN|date=September 27, 2017|access-date=September 27, 2017|archive-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928150228/http://www.msn.com/en-us/entertainment/celebrity/hugh-hefner-playboy-magazine-founder-and-star-of-girls-next-door-dies-at-91/ar-AAsyeDX?li=BBnbfcL|url-status=live}}</ref> Hefner also made a voice-only appearance as himself in the 2011 film ''[[Hop (film)|Hop]]''. In 2012, Hefner announced that his youngest son [[Cooper Hefner|Cooper]] would succeed him as the public face of ''Playboy''.<ref>{{cite news | title= Playboy's Hugh Hefner and son Talk Succession | work= The Wall Street Journal | url= http://live.wsj.com/video/playboy-hugh-hefner-and-son-talk-succession/6D8B6BA4-6808-4772-AF48-68D7EF9366E6.html | date= November 29, 2012 | access-date= September 18, 2013 | archive-date= November 15, 2013 | archive-url= https://web.archive.org/web/20131115124547/http://live.wsj.com/video/playboy-hugh-hefner-and-son-talk-succession/6D8B6BA4-6808-4772-AF48-68D7EF9366E6.html | url-status= live }}</ref>
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