...Hefner, above all, was committed to the liberties of all; not just the lifestyle of would-be playboys, but also those fighting for civil rights, those who were still falling foul of repressive laws, those who desired liberty but found it being shamefully restricted. So at his Playboy clubs during the 1960s, you could hear black comedians perform when most other comedy clubs were still segregated. (Indeed, he even gave $25,000 to one of those comedians, Dick Gregory, to use as a reward for information regarding the murder of three young civil-rights activists in Mississippi, as a result of which convictions were successfully brought against several KKK members.) You could find Hefner in the 1970s, his hands deep in his pockets, funding Jesse Jackson’s civil-rights group, the Rainbow PUSH coalition; and you could find him supporting the comedian Lenny Bruce when many others had abandoned him because of his obscenity convictions. In the words of Hefner’s daughter, Christie, he couldn’t bear to see anyone ‘persecuted or prosecuted for his words and his ideas’.

In the 1980s, he enshrined his commitment to freedom of expression by founding the Hugh Hefner First Amendment Awards. The diversity of the recipients testifies to Hefner’s awareness that fundamental freedoms have to be universal. The list includes women and men, right-wingers and left wingers, Muslims and atheists, and even a pair of magicians in Penn and Teller. It shows that Hefner was willing to support anyone who made the case for greater freedom of thought and speech, from campaigners against government spying in the name of counterterrorism to those who sought to end blacklisting in the television industry. — Tim Black

The days of sneaking away someone's dad's Playboy seem like such innocent times compared to today's internet. — Hanover