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Hugh Hefner was never one to shy away from the spotlight.
The late Playboy founder, regularly clad in silk pajamas, was constantly surrounded by attractive women both on and off camera. Hefner, who died of natural causes Wednesday, Sept. 27, made cameos in a wide range of TV shows and films, from The Simpsons and Roseanne to Curb Your Enthusiasm.
The Hollywood Reporter takes a look back at his most memorable cameos on television and in film.
'The Odd Couple' (1974)
Hefner made an appearance as himself in the season 4 episode "One for the Bunny." Felix (Tony Randall) is hired to photograph a centerfold for Playboy. The inevitable problem occurs when Felix learns the photograph he is taking is of his ex-wife. Felix and Oscar (Jack Klugman) come face to face with Hefner in the episode when Felix refuses to give the Playboy editor-in-chief the photos. The ever gracious Hefner ends up letting Felix keep the photos.
'Beverly Hills Cop ll' (1987)
In the film, Axel Foley (Eddie Murphy) pays a visit to the Playboy Mansion to confront the villainous Maxwell Dent (Jürgen Prochnow). Hefner appears behind Axel to see what the problem is between the two men. While speaking to Hefner, Axel tries to reveal that Maxwell is a bad guy. The host then proceeds to kick everyone involved in the altercation out of the party.
'The Simpsons' (1993)
Hefner lent his voice to the season 4 episode "Krusty Gets Kancelled." When Bart (Nancy Cartwright) is given a grand tour of the Playboy Mansion, Hefner acts as his tour guide. During the tour, Bart learns that there are many unexpected features in the mansion including a biosphere, a laboratory and a research center focused on alternative energy.
In the season 9 episode “What a Day for a Daydream,” Roseanne (Roseanne Barr) imagines what life would be like if she won the lottery. After Roseanne participates in a photo shoot for Playboy where she is covered in money in a bathtub, Hefner appears in his signature red silk robe. In the daydream, Roseanne refers to him as “Hef” and thanks him for revolutionizing “America’s puritanical morals.” He then tells Roseanne that she is “the most beautiful woman on this earth.” Hefner’s cameo begins at 16:22 in the above video.
'Sex and the City' (2000)
In the third-season episode, “Sex and Another City,” Samantha (Kim Cattrall) introduces herself to Hefner while the girls are in Los Angeles. When Samantha tells Hefner that she’s a huge fan, he invites her to have a drink with two other women. She says, “Drinking with three blondes. I guess that’s a regular day for you.” He responds, “A slow one, yes.” The three women then laugh like it’s the funniest joke they’ve ever heard.
In the season 2 episode “Aquamansion,” Vinny (Adrian Grenier) and the crew pay a visit to the Playboy Mansion. The group disregards the fact that Johnny “Drama” (Kevin Dillon) had been banned from the mansion 10 years earlier when he let a bunch of chimps run wild at a party. But it's later revealed that Pauly Shore is responsible for the chimp incident, causing Hefner to ban him.
'Curb Your Enthusiasm' (2005)
In the season 5 episode titled “The Smoking Jacket,” Larry brings a "Make-a-Wish" kid that he meets at the hospital, who wants to see a naked woman, with him to visit the Playboy Mansion. After scaring off all of the bunnies in the pool, Larry goes inside the mansion to use the restroom. He then runs into Hefner, accompanied by two women, wearing a smoking jacket. Larry notices that the coat bears a striking resemblance to one that his father has, so Hef tries on Larry's dad's jacket.
'Family Guy' (2007)
Hefner took another turn at voice acting when he appeared in the season 5 Family Guy episode, "Airport ’07." Quagmire (Seth MacFarlane) is in need of a pep talk after feeling down about his pilot skills, so the animated Hef tells him the story of John Holmes, “the greatest porn star who ever lived.” According to Hef, Holmes’ last words were “Glenn Quagmire is the best damn pilot I’ve ever seen.” The anecdote was all Quagmire needed to give his career as a pilot another try.
'The House Bunny' (2008)
The film stars Anna Faris as Shelley Darlingson, a Playboy bunny who was kicked out of the mansion by a jealous housemate. In need of a new home, Shelly becomes a house mother for a sorority of misfits. Hugh Hefner makes a cameo as himself in the film and is accompanied by beautiful women in the majority of his scenes. When Hefner learns the real reason Shelly left the Playboy Mansion, she receives a personal invitation from Hefner to return.
'Miss March' (2009)
The 2009 comedy is about Eugene (Zach Cregger), a young man who wakes up from a coma to learn that his virginal girlfriend is now a Playboy centerfold. Eugene and his best friend Tucker (Trevor Moore) decide to embark on a road trip to the Playboy Mansion. When Tucker makes his way into the mansion, he runs into his idol, Hugh Hefner.
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