@MaddieM4 @troy_frizzell I did this a little more and found a few other interesting factoids about Playboy / Hugh Hefner:
1. The first short story he ran in the magazine was a SFF that had been refused elsewhere about a straight man constantly discriminated against by a homosexual society. When readers complained that it was wrong to portray a heterosexual being discriminated against, he responded that it's exactly as wrong in reverse – ie, he was a very early advocate for gay rights.
2. Someone recommended he call his centerfolds "Playthings." He replied that women weren't things, but equal partners, including in bed, and so named them "Playmates."
3. Playboy was the first mainstream men's magazine to feature a trans female centerfold.
4. The foundation Hefner started funded the distribution of the newly invented "rape kit" that made it easier for women to identify and convict their male assailants.
Again, I'm not saying he wasn't a creepy weirdo by the end of his life, but definitely a more interesting and less terrible guy than I realized!