1. Hef’s mother, Grace Caroline Hefner, once said that she was proud of him, but would have been equally proud if he’d been a missionary, instead. Hefner later responded, “But mom, I was!” 2. Hefner attended Northwestern University for a semester, taking graduate courses in women and gender studies and sociology. 3. In 1979, Hefner’s daughter, Christie Hefner, created the Hugh M. Hefner First Amendment Award to “honor individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans.” 4. Hefner has said his best sexual experience involved his girlfriend and 17 other playmates in the grotto on his birthday. 5. After a short honeymoon in Wisconsin with his first wife, Mildred Williams, whom he met in college, the newlyweds moved in with Hefner’s parents. The couple divorced 10 years later. 6. In high school, Hefner was popular and voted as one of the students most likely to succeed. 7. The Playboy Mansion is one of the only private homes with a zoo license. 8. Hefner published the first issue of Playboy in 1953 with Marilyn Monroe featured on the cover. He omitted the cover date because he didn’t know when or if he’d be able to publish the next issue. 9. In 1967, Time labeled the Playboy Mansion as the leader in “spectator sex.” 10. Hefner is the 9th cousin, twice removed, of President George W. Bush, and the 9th cousin, once removed, of Senator John Kerry. 11. In 1970, Hefner owned a private jet worth $5.5 million. The Big Bunny, as it was called, was a modified 119-foot long DC-9, equipped with a living room, disco, and sleeping quarters suitable for up to 16 people. 12. Hefner has admitted to experimenting with homosexuality in the past. One evening in Chicago, a man offered to give Hefner fellatio, and Hefner agreed.
13. The first issue of Playboy sold just over 53,000 copies, and was considered a success. 14. Hefner served in the US Army for two years as a camp clerk at the end of WWII after graduating from high school in 1944. 15. Referring to the misery of his first marriage, Hefner once said, “My marriage was like the jobs I had before I started Playboy — the kind of compromises most of us make in the adult world.” 16. When Hefner was 11-years-old he received an award from the Illinois Humane Society for his poem “Be Kind to Dumb Animals.” 17. The first Playboy nightclub opened in Chicago in 1960. Playboy Bunnies served drinks to members, who were known as “keyholders.” 18. In 1963, authorities arrested Hefner in Chicago for possessing indecent photos of actor Jayne Mansfield from the film Promises! Promises! 19. Cynthia Maddox, once Playboy‘s assistant cartoon editor, has appeared on the cover of the magazine 5 times. 20. In the early years, Hefner was serious about publishing good fiction in his burgeoning magazine, and recruited some of the best writers around, such as John Steinbeck, James Baldwin, John Updike, Doris Lessing, Kurt Vonnegut, Vladimir Nabokov, and Michael Crichton. 21. Friends and family lent Hefner $8,000 to start Playboy. 22. In college, Hefner edited the campus humor magazine, Shaft, and introduced a new series titled “Coed of the Month.” 23. Hefner’s parents were both strict Methodists. Hefner once said, “In many ways it was my parents who, unintentionally, developed the iconoclastic rebellion in me.” 24. As a despondent 26-year-old, Hefner stood on a bridge in downtown Chicago and asked himself, “Is this all there is? Where is my life going?” In that moment Hefner says he decided to do something worthwhile with his life.
25. The first Kinsey Report on male sexuality, published in 1948, sparked a large degree of interest in the young Hefner, who went on to research anything to do with sex, from medical journals to law documents. 26. In 1988, Hefner’s daughter, Christie Hefner, became the chief executive officer of Playboy Enterprises. Christie stepped down from her position at Playboy in 2009 to pursue charity work. 27. While Hefner was away in the Army, his then-girlfriend and future wife, Mildred Williams, cheated on him. Hefner said it was “the most devastating moment of my life.” Allegedly, after her affair Mildred let Hefner sleep with other women because she felt guilty and hoped the agreement would save their relationship. 28. As a child, Hefner had a favorite blue-and-white blanket, which featured a bunny pattern. 29. Hefner originally thought of calling his magazine “Stag Party,” but decided against it since it sounded too similar to Stag, which was an outdoor living magazine at the time. 30. The first African-American centerfold was Jennifer Jackson, in the March 1965 issue. 31. Hefner graduated from the University of Illinois at Urbana-Champaign with a B.A. in psychology. 32. Robert Downey, Jr. is in talks to play Hefner in an upcoming biopic. 33. In 1978, Hefner helped raise money to restore the Hollywood Sign. In 2010, he donated $900,000 to the Hollywood Sign Trust to save the sign from demolition. “The sign is Hollywood’s Eiffel Tower,” said Hefner. 34. The best-selling issue of Playboy was the November 1972 edition, which sold 7,161,561 copies. It featured a cover image Lena Söderberg, a Swedish model, shot by photographer Dwight Hooker. 35. In 1989, Hefner married Kimberly Conrad, 1989’s Playmate of the Year. The two have since separated. 36. Hefner once worked as a staff member at Child Life Magazine.
37. Hefner owns the burial crypt next to Marilyn Monroe at Westwood Memorial Park in Los Angeles. 38. In 1951, Hefner published a collection of his own racy cartoons, titled That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals. 39. At Hefner’s Chicago mansion, a sign over the front door reads in Latin, “Si Non Oscillas, Noli Tintinnare,” which translates into “If You Don’t Swing, Don’t Ring.” 40. Hefner is vehemently against drugs, and bans them from his property. 41. Before starting Playboy, Hefner left his job as copywriter at Esquire after the magazine refused to give him a pay raise of $5 per week. 42. In 2005, Hefner wanted to start an Indian version of Playboy with Bollywood actor Aishwarya Rai appearing on the cover of the first issue. The proposed version, however, would contain no nudity. 43. Hefner has personally interviewed every “Girl of the Month” in Playboy‘s history. 44. Glenn Hefner, Hugh Hefner’s father, was born in a sod house and grew up in southern Nebraska. 45. Hefner often describes his approach to life using the words of playwright Dennis Potter: “I want to find a place where the words to the songs are true.” 46. As a boy, Hefner had a dog named “Wags.” 47. In his opening editorial, Hefner positioned Playboy in opposition to outdoor men’s magazines, writing, “We don’t mind telling you in advance — we plan on spending most of our time inside. We like our apartment. We enjoy mixing up cocktails … and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex.” 48. Hefner once tried to set up a foursome with his wife, Mildred, his younger brother Keith, and Keith’s wife, Rae. Apparently Mildred and Keith backed out, while Hefner followed through and slept with his sister-in-law.
49. When Hefner was 9-years-old he published a one-page newspaper called the Bi-Weekly News, which he sold for a few pennies each to some adults in his neighborhood. 50. Hefner has over 18,000 scrapbooks detailing nearly everything that has happened to him over the past 70 years. The collection is stored on the third floor of the Playboy Mansion. 51. The first issue of Playboy contains a Sherlock Holmes story by Sir Arthur Conan Doyle. 52. As a schoolboy, Hefner would get in trouble for spending more time drawing comic strips than doing his homework. 53. Hefner’s first Playboy Mansion was located in the city of his birth, Chicago. 54. A certain species of rabbit, Sylvilagus Palustris Hefneri, was named in honor of Hefner. 55. Growing up, Hefner and his younger brother, Keith, shared a bedroom. The two were separated and given their own bedrooms after their parents grew tired of being kept awake from the brother’s incessant talking and giggling at night 56. Hefner has his own personal cookie drawer in the kitchen at the Playboy Mansion. 57. Hefner was once quoted as saying, “The major civilizing force in the world is not religion, it’s sex.”