Remembering Hugh Hefner's Hilarious 'Curb Your Enthusiasm' Episode

Hugh Hefner was gross. Yeah, his Playboy empire left a specific and indelible stamp on popular culture, and until recent years, he maintained a level of iconography that was impressive for a guy who marketed softcore pornography to the masses—but he was still gross.

And it's OK to think that! If you work or live on the internet (is there any difference between the two?), you're likely to be barraged with an ocean of what the kids call "takes" when it comes to the deceased 91-year-old mogul. You'll likely hear how he was a proponent of free speech, as well as some stuff about changing the way we all think about bunny ears. Those things are true, I guess! Also, he was gross. Also, you don't have to have any opinion at all! The man wasn't Barack Obama—he founded a nudie mag and got rich. It couldn't be simpler than that.

One good thing Hugh Hefner was involved with, if indirectly so, was the 2005 episode of Curb Your Enthusiasm, "The Smoking Jacket." A large portion of the episode takes place at the infamous (and infamously depressing) Playboy Mansion, but instead of explicitly centering the action on how cool it would be to attend Hefner's grody grotto, the episode slyly, hilariously, and possibly unintentionally pokes fun at the iconography surrounding the brand itself.

The main conceit is that Larry's manager and confidant, Jeff Greene (Jeff Garlin), has been invited to the mansion and wants Larry to join him—but Larry's already in trouble with his wife, Cheryl (Cheryl Hines), and is hesitant to make her angrier. In turn, Jeff explains to him the "double transgression theory"—basically, that there's no sense in worrying about making Cheryl any angrier, because she's already angry. How much angrier can she get?

The callousness is obvious, and a tenet of what makes Curb Your Enthusiasm so funny: Sure, visiting a house filled with half-naked women might make your wife angry, but hey, she's angry anyway, so does it even matter? For most people, the answer is a clear and certain "yes," but Larry David is not like most people, and there's a certain and very funny thrill to watching him act so selfishly in moments like these.

As the episode title suggests, there's also a subplot about switching jackets with Hefner himself, as well as one involving a Make-A-Wish kid's desire to see a naked woman. The latter is a bit Benny Hill-ish, which is to be expected. The former is a bit surreal, if only because it's always very surreal to see Hefner trying to be "in character." For a guy who has so often professed himself a lover of all things Hollywood, he also came across as painfully awkward on camera. ("I am, publisher of Playboy or no, a very shy man," he claimed in a 1986 Rolling Stone profile, while addressing charges of him allegedly raping late Playmate Dorothy Stratten.)

And anyone who's seen an episode of the infamous E! reality show The Girls Next Door—Hefner squirming and mumbling his way out of conversations with his titular and multiple girlfriends, remaining a ghostly arms' length from the show's central action amidst the barrel-scraping-ness of it all—knows that he's not camera-ready. He's no different in "The Smoking Jacket," but just as with life in general, you can still enjoy it without acknowledging his presence.

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