Hugh Hefner’s Best TV and Movie Cameos

Hugh Hefner passed away at the age of 91 on Wednesday, September 27, leaving behind an iconic legacy as the founder of the Playboy franchise. Throughout his decades in the spotlight, the media mogul also left a lasting impression on the TV and movie industries in several notable cameos. Here, Us Weekly has rounded up Hefner’s best onscreen appearances. Read about some detailed below and watch them all in the video above.

Sex and the City

Hefner poked fun at his romantic life, which often included a multitude of blonde girlfriends, during a 2000 episode of the hit HBO series. “Drinking with three blondes,” Kim Cattrall’s character Samantha Jones says to Hefner in the clip, “I guess that’s just a regular day for you.” Without missing a beat, the Playboy founder quips, “A slow one, yes.”

Family Guy

Hefner got animated for the FOX series as he offered sex enthusiast Quagmire some well-rounded career advice. “I don’t deserve to be a pilot,” Quagmire, voiced by Seth MacFarlane, says in the 2007 clip. “I’ve let everybody down.” Hefner asks: “Did you do the best you could?” to which Quagmire replies, “No. I was gonna, but I ended up getting laid instead.”

Entourage

Appearing alongside then-girlfriends Kendra Wilkinson, Holly Madison and Bridget Marquardt, Hefner appeared on the HBO series in 2005 to reprimand Kevin Dillon’s Johnny Drama for letting his pet monkeys out of the cage during a party at the Playboy Mansion.

See more of Hefner’s memorable onscreen moments in the video above.

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