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01
Hefner was a longtime gay rights activist. In 1955, he personally chose to publish The Crooked Man by Charles Beaumont in Playboy, a story about a heterosexual man persecuted in a homosexual society. He defended the story against criticism.
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02
Hefner had a Genius IQ of 152 in high school but was described as an unenthusiastic student.
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03
He previously worked for Esquire magazine and left after being denied a $5-a-week raise to found Playboy.
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04
A full-size silicone replica of Hefner is displayed at the Madame Tussaud’s Interactive Wax Museum at the Venetian Casino/Resort in Las Vegas, Nevada.
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05
In 1963, he was arrested in Chicago for possessing indecent photos of actress Jayne Mansfield from the 1963 film Promises….. Promises!
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06
He was raised by rigid Methodist parents. His mother was one of 45 investors he recruited to launch Playboy.
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07
At one time, he owned a 119-foot-long DC-9 jet called the Big Bunny, painted black with the Playboy bunny logo on its tail.
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08
He purchased the burial vault next to Marilyn Monroe at Westwood Memorial Park for $75,000 in 1992, saying spending eternity next to Marilyn is an opportunity too sweet to pass up.
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09
As a young boy, his most prized possession was a blanket covered with little bunnies, which inspired the name of his magazine.
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10
Hefner’s will requires beneficiaries to remain clean and sober; they can be required to pass drug tests to receive trust funds.
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11
He was adamantly against drug use and refused to allow them in any of his houses; anyone caught doing drugs at the Playboy Mansion faced permanent expulsion.
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12
His original plan was to call his magazine Stag, but another magazine already had that title. Playboy was his second choice.
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13
He was the first magazine publisher to become a major celebrity.
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14
A species of rabbit, Sylvilagus palustris hefneri, was named in his honor.
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15
A brass plaque over the front door of his Chicago mansion reads Si Non Oscillas, Noli Tintinnare—Latin for If You Don’t Swing, Don’t Ring.
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16
In 1988, he turned his empire over to his daughter Christie Hefner.
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17
He personally interviewed every Playmate of the Month in his magazine’s over 50-year history.
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18
Marilyn Monroe was the centerfold in the very first issue of Playboy in December 1953; that issue was the only one to use the title Sweetheart of the Month. The magazine was originally going to be called Stag Party.
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19
He served in the U.S. Army in WWII after graduating from Steinmetz High School in Chicago in 1944.
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20
In 2005, he attempted to create an Indian version of Playboy featuring South Asian women and Indian popular culture without nudity, but the magazine was rejected.
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21
He had an extensive film collection and ran a Saturday Night Mansion Movie every week at the Playboy Mansion, showing movies that sometimes hadn’t been released to theaters yet.
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22
He resided with Barbi Benton from 1969 to 1976.
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23
His father had German and English ancestry; his mother was of Swedish descent.
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24
He had legal battles with Hustler Magazine over his photo collections.
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25
He created the world-famous Playboy Mansion in Los Angeles, California in 1971.
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26
His children include Christie Hefner born in 1952 and David Paul Hefner born in 1955 by Mildred Williams, and Cooper Hefner and Marston Hefner by Kimberley Conrad. David owns a computer consulting firm.
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27
He played a major role in the James Bond short story A Midsummer Night’s Doom by Raymond Benson.
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28
He claimed to be a direct descendant of pilgrim leader William Bradford.
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29
He had a round-the-clock kitchen staff to serve him meals on a tray in bed and kept his own drawer of cookies in the Playboy Mansion’s kitchen.
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30
He was awarded a star on the Hollywood Walk of Fame for Television at 6126 Hollywood Boulevard on his 54th birthday, April 9, 1980.
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31
Magazine mogul Jerry Caesar from the TV series Dragnet in 1987 is based partly on him and Larry Flynt.
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32
He originally worked on the publishing staff of Child Life magazine.
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33
He helped radical comedian Dick Gregory get famous; he and Gregory died about a month apart.
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34
His parents Glenn and Grace Hefner were from Phelps County, Nebraska.
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35
Between 1959 and 1974, the hub of the Playboy universe was at 1340 North State Parkway, Chicago, Illinois, just a block from the Cardinal’s residence.
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36
He appeared on the cover of the November/December 2017 issue of Playboy, making him the 11th man to appear on its cover and the first solo male cover without a female model.
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37
He graduated from Steinmetz High School and also from the University of Illinois. As a child, he often visited the now demolished Mont Clare Theatre in Chicago.
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38
He was pictured on a souvenir sheet issued by Grenada & the Grenadines on December 1, 2003, celebrating the 50th anniversary of Playboy.
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39
He was formerly engaged to Crystal Harris; she called off the engagement days before their wedding in June 2011, but he allowed her to keep the engagement ring and a customized Bentley.
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40
He and Jenna Jameson share the same birthday, April 9th.
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41
He grew up in the Montclare neighborhood of Chicago, Illinois.
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42
He was mentioned by Arsenio Hall as Reverend Brown in Coming to America from 1988 while giving a sermon.
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43
Playboy Magazine sold stories, including horror stories; Christopher Pike’s novel The Eternal Dawn makes oblique references to the Twilight series and is a story sold to Playboy.
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44
He was the creator and publisher of Playboy Magazine.
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45
He was friends with Bill Cosby and Bill Maher.
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46
He had an older brother, Keith Hefner.
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47
He was the late father-in-law of William A. Marovitz.
