But others pointed out that while Hefner launched his brand and his lifestyle off the back of that first Playboy issue in December 1953, Monroe was embarrassed by the shoot that appeared in it - and feared for her future career.
The son of an accountant and a teacher, both conservative Protestants from Nebraska, Hefner over the years spoke out against sodomy laws.
Before he became the symbol for the single lifestyle, Hefner was married to Mildred Williams in 1949. They had two children, Christie and David.
"He said, 'Well, we certainly wouldn't shoot you!'"
Playboy also printed letters to the editor that served as a sort of conversation between the publication and its readers.
Her post was accompanied by an image in which she is seen with Hefner, who is dressed in a deep red bath robe, while she is dressed in black.
Perhaps the most noteworthy critique of the world Hefner built came from feminist Gloria Steinem.
- Anna Nicole Smith: The model landed her first Playboy cover in March 1992 with the name Vickie Smith. "Rest In Peace my friend", added Hilton who shared a photo of herself next to Hefner while wearing the magazine's iconic Playboy bunny outfit. He's credited with ushering in a sexual revolution and propelling the notion that all women had the right to sexuality.
Media mogul Hugh Hefner died Wednesday at age 91. The couple divorced in 2010.
Even Dolly Parton was a cover girl in the 1970s.
Though he could not cite a definitive number, he assured Esquire in 2013 he was "sure" he had slept with "over a thousand" women. "Godspeed, Hugh Hefner", wrote music legend Frank Sinatra's daughter, Nancy Sinatra. "You gave me life", Anderson wrote alongside a video of herself crying on her bed. "He will be greatly missed by many".
While another commented: "Omg, you look like a doll, you're soooooooooo beautiful my love".
The late Hugh Hefner once wanted to recruit Margot Robbie for the pages of his magazine. He was a gift to us that we will never experience again.
"I'm a human rights activist", Hefner said in a 1994 Advocate interview when asked if he considered himself a gay rights activist.