Playboy magazine founder Hugh Hefner poses at his Playboy Mansion in Los Angeles in 2010.
Hefner built Playboy into a multimillion-dollar adult magazine and entertainment empire tied to a Lothario lifestyle of lavish parties and beautiful women.
Hefner holds the first issue of Playboy, featuring actress Marilyn Monroe, circa December 1953.
Hefner poses with "bunnies" at the flagship Playboy Club in Chicago circa 1960.
Hefner poses with hostess Bonnie J. Halpin at his nightclub in Chicago in June 1961.
Hefner looks at photographs of models in his Chicago office.
Hefner's magazine brought female nudity out of bachelor parties and into living rooms, and it played a leading role in the sexual revolution of the 1960s.
Hugh Hefner in 1963.
Hefner and his girlfriend Barbara Benton, a 19-year-old actress, are surrounded by bunnies at the Playboy Club in London in 1969.
James Avery and Hugh Hefner attend a pool party at the Playboy Mansion in a scene from "The Fresh Prince of Bel-Air" in 1993.
The mansion has been the scene of countless movies and TV series.
Hefner pushes his second wife, Kimberly, on a bicycle at the Playboy Mansion in 1996. The couple divorced in 2010 and Hefner was married to former Playmate Crystal Harris in 2012.
Playmates, from left, Holly Madison, Bridget Marquardt and Kendra Wilkinson pose with Hefner as they arrive at Columbia Pictures' premiere of "House Bunny" at the Mann Village Theater in Westwood, California, in 2008.
Hefner is kissed by his two girlfriends at the Hotel de Paris in Monaco in 2009.
The Playboy Mansion in Los Angeles.
Hugh Hefner kisses Pamela Anderson at a book signing in Beverly Hills in 2009.
Hefner arrives at Stansted Airport in England in 2011.
Hefner and his son Cooper attend the Annual Midsummer Night's Dream Party at the Playboy Mansion in 2014.
The first edition of Playboy magazine in 1953 featured Marilyn Monroe on the cover and as a centerfold.
The Playboy that featured Pamela Anderson in February 2016 was meant to be the last one featuring nude pictures, ending a more than 60-year tradition that saw women from Madonna to Kim Kardashian and Cindy Crawford pose naked for the publication. The move was only temporary, however, and the magazine began publishing images of naked women again earlier this year.
Fans gather at the gate of the Playboy Mansion on Sept. 27, 2017, after hearing of Hefner's death.
Related: Hugh Hefner Dies at 91