If you believe what the documentary Hugh Hefner: Playboy, Activist and Rebel would have you believe (and there's no reason not to, to a degree), Hugh Hefner had a hand in every major progressive battle of the past century: civil rights, desegregation, unjust sodomy laws, censorship, McCarthyism, sexual liberation, drug legalization, contraception, abortion, the Vietnam War, the separation of church and state, and even—depending on who you talk to—feminism. At one point in the film, Mike Wallace draws a very earnest and direct correlation between Hefner's integrated nightclubs in the 1960s and Barack Obama's election in 2008.
Obviously, the guy is a charming fellow and a genius of a businessman, and he made some truly brave and groundbreaking moves that changed the 20th century for the better. He's also the kind of guy who can start an anecdote with "So Yul Brynner called..." and end it with "and there were babies everywhere!" I like Hugh Hefner. I really do.
On the other hand, Hefner is also responsible for one of the most powerful, ubiquitous, and self-perpetuating engines of female objectification and commodification in the history of the world. In Playboy magazine, the women take off their clothes and the men write intellectual essays. The women are decoration, and there's simply no getting around that, no matter how much "fun" everyone appears to be having. On the other hand, all of us want to be objectified in certain ways, and if women can make money off their bodies and holes, that's their right. On the other hand, the balance of sexual power in the world is grossly unequal, even in 2010. On the other hand, boobies!!!
Joan Baez, who appeared on Playboy After Dark in 1968, mentions the cognitive dissonance inherent in Hefner—in reconciling "the politically conscious side" (pause, sigh) "and the bunny side." It's no secret where this film comes down, though it gives admirable lip service to what Jenny "Dr. Autism, MD" McCarthy calls "the old feminism" (they had some good ideas, McCarthy offers, but it's time for the new feminism to "take it to the next level"—i.e., boobies!!!).
Susan Brownmiller—most famously the author of 1975's Against Our Will: Men, Women and Rape—appears, wry and resigned, to say, "Hugh Hefner was a very clever fellow, and also, I think, a very dangerous fellow." The film, though, is really more interested in what Gene Simmons has to say: "Hugh Hefner, probably single-handedly more than any other man perhaps in history, made it okay for women to also like sex." Cut back to Brownmiller's exploding head. "Playboy did not speak to women. Women were used in Playboy for men's masturbatory fantasies." Cut back to Simmons's penis. And cue the self-serving, not very satisfying argument: The arc of the moral universe may be long, but it bends toward Jenny McCarthy's boobies. 
