When I was growing up, there were 3 things on the back of the toilet in the family bathroom: a Bridge (card game) magazine, Playboy and if I was really lucky, the Wall Street Journal.
I was really young, so I always got excited when a WSJ was left, but I liked to read on the back of the toilet and naturally opened them up.
From a young age, I got to read AMAZING interviews and cutting-edge literature as well as get to see nude women who were very attractive and natural (this was in the 70s and very early 80s). So I grew up with this image that women were fantastic, beautiful, complex PEOPLE who had their own wants, needs, and desires. This as opposed to the first time many years later I saw a Penthouse and I thought even as a youth that Penthouse was more about a man's projection of a woman versus how a woman would choose to present themselves. I honestly found Penthouse to be offputting.
Much of what I learned from those pages, from the ribald humor to the raunchy jokes to the revolutionary cultural content, has served me well as a man, husband, father, and citizen.
Hef led the charge to talk about sex, sensuality, and sexuality a fun and real way. At least at the time, the women were natural (was before the airbrushed poses), beautiful women who existed in the world. Most of them weren't actresses or models as well.
Everyone has their favorites... 25th Anniversary with Candy Loving sitting in that Champagne cup...blew my mind. The Kim Basinger edition where she became Playmate of the year. I truly feel that Kim Basinger's PotY layout was as much as an homage to the ideal female figure as Arnold Schwarzenegger's poses were an homage to the male form. There were others as well as the editions with interviews of Alex Haley, Wilt Chamberlain, Fidel Castro, and so many others...
Playboy was part of a movement as well as moment.
I would further argue that it wasn't porn at all, but erotica and literature at a time when those boundaries were able to be pushed. Moreover, it wasn't about being extreme, but fun, honest and real.
His stance on fighting segregation is very important, too. Very important.
He became a bit of a caricature at the end, but his legacy is far more important than his iconic pipe and robe.