Since then a number of notable Black actresses, models, singers, and rappers have graced Playboy's cover — Mariah Carey, Naomi Campbell, Tinashe, and even Azealia Banks among them. And that’s not the only way Hefner and his brand has co-mingled with hip-hop. One of my favourite episodes of The Fresh Prince of Bel-Air is the one where Hilary Banks (Karyn Parsons) is approached to pose for a fictional weather girl edition of the magazine. Hefner appearing next to a then-rapper Will Smith and DJ Jazzy on the sitcom was just one example of how the icon is revered by the community. You can imagine how his lifestyle — one with wealth and sex constantly within in reach — synced up some of the more popular moors of contemporary hip-hop. Today, in the wake of his death, he is being mourned by everyone from Questlove to Diddy.