Hugh Hefner

Founder and Editor-in-chief of Playboy Magazine
Born Apr 9, 1926

Hugh Marston "Hef" Hefner is an American magazine publisher, founder and chief creative officer of Playboy Enterprises.

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Learn about the memorable moments in the evolution of Hugh Hefner.


1926 Birth Hugh Hefner was born in Chicago, Illinois on April 9, 1926. … Read More


1944 18 Years Old He attended Sayre Elementary School and Steinmetz High School, then during World War II, served as a writer for a military newspaper in the U.S. Army from 1944 to 1946. … Read More


1949 23 Years Old In 1949, Hefner married Northwestern University student Mildred Williams (born 1926). … Read More
1952 26 Years Old Working as a copywriter for Esquire, he left in January 1952 after being denied a $5 raise.
1953 27 Years Old 1 More Event
In 1953, he mortgaged his furniture, generating a bank loan of $600, and raised $8,000 from 45 investors, including $1,000 from his mother ("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.
1955 29 Years Old After it was rejected by Esquire magazine in 1955, Hefner agreed to publish in Playboy the Charles Beaumont science fiction short story "The Crooked Man", about straight men being persecuted in a world where homosexuality was the norm. … Read More


1959 33 Years Old The two were divorced in 1959. … Read More
1961 35 Years Old In 1961, Hefner watched Dick Gregory perform at the Herman Roberts Show Bar in Chicago. … Read More
1963 37 Years Old On June 4, 1963, Hefner was arrested for selling obscene literature after an issue of Playboy featuring nude shots of Jayne Mansfield was released. … Read More


1971 45 Years Old 1 More Event
In 1971, he acknowledged that he experimented in bisexuality.


1985 59 Years Old Hefner had a minor stroke in 1985 at the age of 59. … Read More


1998 72 Years Old After he and Conrad separated in 1998 she moved into a house next door to the mansion.
2009 83 Years Old In 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.
…  The relationship with the twins ended in January 2010. … Read More
2011 85 Years Old Hefner and Harris had planned to marry June 18, 2011. … Read More
The two later reconciled, and on December 31, 2012, Harris and Hefner married at the Playboy Mansion in a small private ceremony; he was 86 and she was 26.
2016 90 Years Old In January 2016, 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. … Read More
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