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Lois Lee presented Hefner with the organization's first-ever Founder's Hero of the Heart Award in appreciation for his unwavering dedication, commitment and generosity.

Hefner supported legalizing same-sex marriage, and he stated that a fight for gay marriage was "a fight for all our rights.

He admitted to being "'involved' with maybe eleven out of twelve months' worth of Playmates" during some of these years.

Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Barbi Benton, Karen Christy, Sondra Theodore, and Carrie Leigh – who filed a million palimony suit against him – were a few of his many lovers.

In 1971, he acknowledged that he experimented in bisexuality. After re-evaluating his lifestyle, he made several changes.

After the magazine received angry letters, Hefner wrote a response to criticism where he said, "If it was wrong to persecute heterosexuals in a homosexual society then the reverse was wrong, too." In 1961, Hefner watched Dick Gregory perform at the Herman Roberts Show Bar in Chicago.

Based on that performance, Hefner hired Gregory to work at the Chicago Playboy Club; Gregory attributed the subsequent launch of his career to that night.

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