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30 remarkable highlights from playboy’s founder, Hugh Hefner’s fabulous life

American icon and founder of the Playboy empire, Hugh Marston Hefner, has died at the age of 91.
Hefner founded the men’s fantasy magazine with just over $1000 in the 1960s and has recreated the brand several times. Playboy is a brand still recognized today in the reality TV and social media age. brings you 30 remarkable highlights from the life of Playboy’s Hugh Hefner

1. Hefner was born in Chicago, Illinois on April 9, 1926. He is the first child of Grace Caroline (née Swanson; 1895–1997) and Glenn Lucius Hefner (1896–1976), who both worked as teachers.

2. Although, Hefner’s mother was of Swedish descent, and his father had German and English ancestry. Through his father’s line, Hefner stated that he was a direct descendant of Plymouth governor William Bradford.

3. He attended Sayre Elementary School and Steinmetz High School. Hefner graduated from the University of Illinois at Urbana Champaign with a bachelor of arts in psychology and a double minor in creative writing and art in 1949, earning his degree in two and a half years.

4. During World War II, he served as a writer for a military newspaper in the U.S. Army from 1944 to 1946.

5. In 1949, Hefner married Northwestern University student Mildred (“Millie”) Williams, who was also born in 1926. They had two children: daughter Christie Hefner (born 1952) and son David (born 1955). However, they divorced in 1959.

6. Hefner was working as a copywriter for Esquire, and left in January 1952 after being denied a $5 raise.
In 1953, he took out a mortgage, generating a bank loan of $600, and raised $8,000 from 45 investors, including $1,000 from his mother to launch Playboy, which was initially going to be called Stag Party.

7. The first issue, published in December 1953, featured Marilyn Monroe from her 1949 nude calendar shoot and sold over 50,000 copies. Hefner, who never met Monroe, bought the crypt next to hers at the Westwood Village Memorial Park Cemetery in 1992 for $75,000.

8. After the Charles Beaumont science fiction short story “The Crooked Man” was rejected by Esquire magazine in 1955, Hefner agreed to publish it in Playboy.

9. Hefner was later arrested for promoting obscene literature after an issue of Playboy featuring nude shots of Jayne Mansfield was published. The case went to trial and resulted in a hung jury.

10. Hefner financed the Clara Bow documentary and guest-starred as himself in a 2006 episode of Seth Green’s Robot Chicken on the late-night programming block Adult Swim.

11. In 2009, he received a “worst supporting actor” nomination for a Razzie award 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.”

12. 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 and 90 episodes.

13. Hefner remade himself as a bon vivant and man about town, a lifestyle he promoted in his magazine and two TV shows he hosted, Playboy’s Penthouse (1959–1960) and Playboy After Dark (1969–1970).

14. Donna Michelle, Marilyn Cole, Lillian Müller , Shannon Tweed, Barbi Benton , Karen Christy , Sondra Theodore , and Carrie Leigh — who filed a $35 million palimony suit against him — were a few of his many lovers.

15. January 2009, Hefner started dating Crystal Harris, joining the Shannon Twins after his previous “number one girlfriend”, Holly Madison had ended their 7-year relationship.

16. He acknowledged that he experimented in bisexuality and he established a second residence in Los Angeles with the acquisition of Playboy Mansion West.

17. Hefner had a minor stroke in 1985 at the age of 59. After re-evaluating his lifestyle, he made several changes. The wild, all-night parties were toned down significantly and in 1988, daughter Christie began to run the Playboy empire.

18. The following year, he married Playmate of the Year Kimberley Conrad; they were thirty-six years apart in age. The couple had two sons: Marston Glenn (born 1990) and Cooper Bradford (born 1991). He dated as many as seven women concurrently.

19. Hefner became known for moving an ever-changing coterie of young women into the Playboy Mansion, including twins Sandy and Mandy Bentley.

20. The Playboy Mansion was put on the market for $200 million, on condition that Hugh Hefner would continue to work and live in the mansion. It was later sold to Daren Metropoulos, a principal at private equity firm Metropoulos & Co, for $100 million.

21. The Hugh M. Hefner First Amendment Award was created by Christie Hefner “to honor individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans.

22. He donated and raised money for the Democratic Party, meanwhile, he supported Barack Obama ‘s reelection campaign.

23. Hefner helped organize fund-raising efforts that led to the restoration of the Hollywood Sign. He hosted a gala fundraiser at the Playboy Mansion and personally contributed $27,000.

24. Hefner donated $100,000 to the University of Southern California’s School of Cinematic Arts to create a course called “Censorship in Cinema,” and $2 million to endow a chair for the study of American film.

25. Both through his charitable foundation and individually, Hefner also contributed to charities outside the sphere of politics and publishing, throwing fundraiser events for Much Love Animal Rescue as well as Generation Rescue, a controversial anti-vaccinationist campaign organization supported by Jenny McCarthy.

26. Children of the Night founder and president Dr. Lois Lee presented Hefner with the organization’s first-ever Founder’s Hero of the Heart Award in appreciation for his unwavering dedication, commitment and generosity.

27. Hefner donated the last $900,000 sought by a conservation group for a land purchase needed to stop the development of the famed vista of the Hollywood Sign.

28. Sylvilagus palustris hefneri, an endangered subspecies of Marsh rabbit, is named after him in honor of financial support that he provided.

29. Hefner supported legalizing same-sex marriage , and he stated that a fight for gay marriage was “a fight for all our rights. Without it, we will turn back the sexual revolution and return to an earlier, puritanical time.”

30. Hefner died of natural causes at his home in Holmby Hills, Los Angeles, California on September 27, 2017, at the age of 91. He is survived by his wife, Crystal Harris and his four children from previous relationships.

  • Chika Okorie for



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