- One awesome moment for Hef and Playboy: he serialized Fahrenheit 451 in a time when Ray Bradbury's novella was being banned and blacklisted by almost all other major publishers.
- Another one for the Hef. A reader wrote in, asking for advice. Turns out the woman he proposed to was MTF transgender, and he was freaking out. Hefner bluntly answered "Big whoop!" and told the guy that this should not be a barrier to a happy marriage at all. ("You already fell in love with her before this") with the implication that the guy in question was being stupid about something very minor. If he wanted kids, there were plenty up for adoption, after all. This was back in the Seventies! Considering American society is still having trouble accommodating transgender people, it makes Hef's advice all the more awesome.
- Hefner also had a sterling civil rights record. The Playboy club was the first mainstream club to feature black performers and civil rights issues were frequently featured in the magazine—its very first interview was with Miles Davis. Other interview subjects included Muhammad Ali, Martin Luther King Jr., and Malcolm X. He donated to the Rainbow Coalition, advocated for gay rights, and for abortion rights nearly a decade before the Roe vs. Wade decision.
- Hef once responded to a Twitter user who asked how he got so many "bitches" as follows:bazooka_Jroe: How do you have so many bitches?!?Hugh Hefner: I have a lot of girlfriends because I don't call them bitches, Jroe. A little respect will take you a long way.
Awesome / Playboy