Film & TV

Hugh Hefner’s 5 Most Iconic Television Cameos

Film & TV

Hugh Hefner’s 5 Most Iconic Television Cameos


As you’ve likely heard, cultural icon and founder of Playboy Hugh Hefner passed away last night at the age of 91. While Hefner is a complicated hero whose fortune and legacy is based largely on the objectification of women, he also played a major role in the sexual revolution, championed a slew of iconic writers (including my other not-so-favorite, Norman Mailer) not to mention a fearless and active supporter of civic rights. Plus, some of those throwback Playboy shoots are simply iconic and, in many ways, celebrated women and their, ahem, assets.

Hef’s impact and permanence is perhaps best exemplified by his many, many television cameos. Your show wasn’t shit until you had Hugh Hefner playing himself and/or a party scene at the Playboy Mansion. Here are a handful of the absolute best.


Of course Entourage, HBO’s landmark bro series, had an episode in which Vinny and his crew went to the Playboy Mansion. Johnny Drama was banned for life for allegedly letting Hef’s monkeys out of the zoo, so Turtle sneaks him in, resulting in a classic Hefner “get this guy outta here” altercation. But my favorite part was, of course, Turtle’s very expeezy pajamas.

Sex and the City

Naturally Samantha idolized Hef. In fact, she had “worshipped him ever since she was old enough to steal her father’s Playboys.” This cameo ends in a “get this gal outta here” when Samantha tries to steal a Playboy Bunny’s Fendi purse, mistaking it for her own, fake Fendi purse. Which leads us to another classic wardrobe mixup…

Curb Your Enthusiasm 

The mere premise of Larry David going to the Playboy Mansion is perfect. Of course when he shows up, the topless bunnies run screaming for no apparent reason. Of course he brings a child with a terminal illness so he can see a naked woman before he dies. And of course he mixes up his father’s smoking jacket with Hef’s smoking jacket. And of course he awkwardly invites Hef’s girls to go bowling sometime. This cameo has everything.

Fresh Prince of Bel-Air

Who could forget the time that Hilary was invited to pose for Playboy? Philip was not amused.

The Simpsons

Hefner, like just about every other cultural icon dead or alive, had a cameo on The Simpsons back when the show was in its prime. Bart is putting together a dream team of celebs for Krusty the Clown’s comeback special, so he swings by the Playboy Mansion to ask Hefner if he’s available. After Hef gives Bart a tour (including “the laboratory, the biosphere and the alternate energy resource center”), Bart goes, “Smart bunnies, Hef. I can call you Hef, can’t I?” To which Hef simply replies, “No.”

Rest in power, Hef.