Hugh Hefner, the well-known publisher of Playboy magazine, had a set of unusual rules for his girlfriends residing at the Playboy Mansion. These rules dictated aspects of their appearance, like hair color, and their behavior, such as adhering to a strict curfew and not interacting with his employees.
Hefner, who launched Playboy in December 1953, became a media sensation by living extravagantly in his mansion and dating multiple women simultaneously, including Holly Madison, often referred to as his ‘number one girlfriend.’ Madison has recently shared insights into her life at the mansion and what was expected of her and other models.
During the In Your Dreams podcast hosted by Owen Thiele, Madison described her experiences with Hefner and the unsettling nature of group interactions. She detailed how group encounters were ‘disgusting’ and that she openly expressed her dislike for them.
Hefner’s control extended beyond personal interactions; he had multiple girlfriends but expected them to remain faithful only to him. Madison’s 2015 memoir, *Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny*, reveals, “While Hef could date an entire sorority house full of girls, we were to remain totally loyal.”
Izabelle St. James, another of Hefner’s former girlfriends, shared her perspective on the peculiar dynamics of dating Hefner. She noted how Hefner created his own world with unique rules and expressed her curiosity to understand more about it.
Hefner’s rules also impacted the appearance of his girlfriends, as he had strong preferences about how they presented themselves. Madison recounted in her memoir that red lipstick was banned because Hefner associated it with older women, favoring a ‘young and fresh-faced’ look for his playmates.
Besides lipstick, Hefner also dictated hair color. Madison explained on the 2021 *Power: Hugh Hefner* podcast that being one of his girlfriends required having blonde hair, with famous blondes like Bridget Marquardt and Crystal Hefner among them. Crystal shared with *People* about the harsh effects of regularly dyeing her hair.
St. James highlighted the strict 9pm curfew, which Hefner enforced to prevent his girlfriends from staying out late and potentially being unfaithful. If girlfriends missed this curfew, Jenna Bentley noted, they could face the consequence of sleeping outside on the lawn.
Bentley also revealed the existence of an ‘iron-clad’ NDA she signed to keep the mansion’s secrets, while Crystal Hefner stated she did not sign any such agreement during her time with Hefner.
Christmas was another time when girlfriends were expected to stay at the mansion, according to Madison’s memoir, although they were given time off before or after the holiday to visit family. During Christmas, Hefner was particularly generous with his girlfriends.
Girlfriends also had to relinquish their previous homes, with Madison noting that some kept apartments secret from Hefner. Some women lived rent-free at the mansion, while others paid for their rooms.
In her memoir, *Bunny Tales: Behind Closed Doors at the Playboy Mansion*, St. James described the cumbersome process of collecting weekly allowances from Hefner, involving waiting for him to clean up after his dogs before receiving their pay. This situation allowed Hefner to voice his grievances about ‘harmony’ among his girlfriends.
Hefner’s stance against drugs and alcohol extended beyond his personal life, influencing the behavior of his girlfriends and heirs. His will explicitly stated that heirs with substance dependencies would be disinherited.
The Playboy Mansion’s operations involved around 80 staff members, with whom Hefner’s girlfriends were prohibited from interacting. St. James and Madison both emphasized the rule against fraternizing with the staff, a rule that Hefner enforced strictly.