It is often said "one man's terrorist is another man's freedom fighter". The publisher of Playboy Magazine was in fact something of a terrorist. His magazine would now an then be banned by a city official, and sellers get arrested women organizations, usually right wing ones, protest the immorality - left wing women were often unsure whether taking off clothes for money is liberation and empowerment, or objectification judges would now and then be asked to pronounce on legal issues of whether nudity is art or free expression in any case, Hefner was in the forefront of movement cutting down censorship in America - over several decades and many test cases, censorship retreated, and Hefner took credit as the great liberator.
More significantly, he actually set himself up as a social philosopher, writing at length about his hedonistic lifestyle's merits I am not sure how many people took him seriously, or even actually read his numerous Playboy Philosophy articles. He certainly practised what he preached, having one new girlfriend after another (sometimes several at the same time) in his 70s he tried to marry for the fourth time but his wedding was cancelled when the bride failed to show up she did briefly go back to him however no wedding took place eventually.
History has not been kind to him. The uncensored social environment meant steady expansion of porn availability, so that his stuff looked tame, old fashioned. Internet made monetization of published content more difficult He himself could no longer put his mind on management, so his daughter Christie from his first marriage came in as CEO for a period of time - she even went to China to open casino, but was not successful later his son from second marriage tried, and was still trying when dad passed away.
It is perhaps fitting that the most remembered photo about him will be trump on cover of Playboy. To balance, I show his portrait with first family.