Hugh Hefner, who died yesterday at 91, was a lot of things — an entrepreneur, a publishing magnate, husband, father, mansion dweller and owner of Holmby Hills' most notorious grotto (I'm sure there are a few). Much has already been written about his place in popular culture — good and bad — but one thing is for sure: He was not an actor. Of course, that didn't stop him from appearing as himself on scripted television shows, beginning in the ’70s with The Odd Couple, all the way into the early to mid 2000s on a trio of HBO shows. Hef was consistently and reassuringly wooden, every ounce a guy who doesn't need the paycheck and has no use for direction but probably doesn't mind the plug for branding purposes. Sadly, not all of these appearances exist on the internet, but here's a list all the same (everything's available somewhere). R.I.P. to a sitcom fixture.
10. Family Guy (2007)
Quagmire doubts his ability as a pilot until he gets a pep talk from Hef, complete with a Seth MacFarlane–style off-color joke about porn star John Holmes' AIDS-related death. According to DVD commentary, they had to add an echo to Quagmire's vocal take in postproduction to match Hefner's, which was recorded in his den rather than a production studio. Atta boy.
9. Curb Your Enthusiasm (2005)
Jeff gets an invite to the Playboy Mansion and brings Larry — and Larry brings a dying tween he met in the hospital whose Make-a-Wish Foundation–style wish is to see a naked woman. Hefner taps into a pet peeve by wearing Larry's smoking jacket into the bathroom. (The quality of this video is maybe the worst I've ever seen, but the episode is available in watchable form on HBO GO.)
8. Entourage (2004)
All of the schmucky guys go to the Playboy Mansion even though Hefner thinks one of them set his monkeys free? Something like that. But this cameo is worth watching if only for the feigned look of concern on Hefner's face when he first spots Vince's crew. OK, and for Pauly Shore.
7. The Bernie Mac Show (2004)
Hefner made a cameo to help Bernie give one of his young charges (his sister's kids, if I remember correctly) "the talk." (The season-three episode is called "The Talk.") All five seasons of Mac's eponymous sitcom are available on Netflix, and might actually be worth revisiting. It was funny the first time around.
6. Sex and the City (2000)
A notorious under-actor meets a notorious over-actor (and sonnet reader) in the season-three episode of Sex and the City when the gals visit L.A. and everything is SO FUCKING L.A. that of course you'd just run into Hugh Hefner at a bar. Hugh's forced laughter at his own bad jokes is sort of endearing. As for Cattrall, no comment.
5. Roseanne (1996)
The show's ninth and final season is a tough sell for even the show's most fervent viewers (like myself). The Conners have won the lottery, and in "What a Day for a Daydream," Roseanne fantasizes about life as a millionaire, which includes a photo shoot with Jackie and Hef. Eh, probably just stick to seasons one through eight.
4. The Larry Sanders Show (1993)
Yes, Jeffrey Tambor is fantastic on Transparent, but man, was he great as Hank, Larry's late-night sidekick. When Hef is a guest on The Larry Sanders Show (like, the show in the show), Hank arranges for Playboy test shots to be taken of his assistant, Darlene, for a spread he's envisioned, called "the sidekick's sidekick." Rip Torn's character, Arthur, jokes that Hank did everything but "hump [Hefner's] leg." Larry replies, "You must've looked away for a second." Also this is one of Hefner's better performances since he's basically just being interviewed for a talk show. (The season-two episode is called "Broadcast Nudes" and it's available on HBO GO.)
3. The Simpsons (1993)
Bart gets a tour of Hefner's Shelbyville mansion in this season-four episode, and Hef reveals that he's an environmentalist on the cutting edge of alternative energy. And the Bunnies are scientists. But, for real, sometimes Bunnies do become scientists.
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2. Laverne & Shirley (1982)
Unlike the typical walk-on cameo with a line or two, Laverne & Shirley gave Hefner an entire scene to flex his acting muscle (sorry) alongside Penny Marshall and Carrie Fisher in Bunny uniforms, which made 1982 even more 1982 than it already was. Laverne and Cathy go head to head for an open position at the Playboy Club, and there are lots of pitfalls and pratfalls and actual glasses of spilled milk.
1. The Odd Couple (1974)
True story: This clip wasn't available online a few hours ago. Bask in the glow of Hefner's purple shirt as Felix proves he's a paternalistic a-hole in the season four episode "One for the Bunny."