3 chapters across the catalog
Holly Madison's memoir, Down the Rabbit Hole, is used to illustrate the routine use of Quaaludes and sexual "rituals" at the Playboy Mansion. Madison describes how Hugh Hefner used drugs to manipulate his girlfriends and pit them against one another. The hosts note the hypocrisy in Hefner being celebrated as an American icon while Cosby was imprisoned for similar behaviors involving the same substances.
Former NBA player John Salley reveals that Bill Cosby lived at the Playboy Mansion for two years while hosting The Tonight Show for Johnny Carson. A 2011 video from the Playboy Jazz Festival shows Cosby and Hefner joking about "presents" (women), which the hosts point out would have canceled any modern figure. This deep connection to the Mansion's culture further complicates Cosby's public image as a moral authority.
A retrospective on Hugh Hefner's life highlights his 1956 debut on CBS, which Adam Curry refers to as the "Central Intelligence Broadcasting System." The hosts discuss Hefner's familial link to George W. Bush and the theory that both he and Gloria Steinem were intelligence assets used to reshape American sexual culture. They also reminisce about the role of National Geographic and Playboy in the "pubescence" of American males.
