Roger Ebert considers Hugh Hefner's legacy:
Hefner and Playboy have been around so long that not everyone remembers what America used to be like. It was sexually repressed and socially restrictive. College students were expelled for having sex out of wedlock. Homosexuality and miscegenation were illegal. Freedom of choice was denied. McCarthyism still cast a pall over the freedom of speech. Many people joined in the fight against that unhealthy society. Hefner was one of them, and a case can can be made that Playboy had a greater influence on our society in its first half-century than any other magazine.
No doubt Playboy objectified women and all the rest of it. But it also celebrated them, and freed their bodies from the stigma of shame. It calmly explained that women were sexual beings, and experienced orgasms, and that photographs of their bodies were not by definition "dirty pictures." Not many of today's feminists (of either gender) would be able to endure America's attitudes about women in the 1950s.