Hugh Hefner's impact on the entertainment industry extended far beyond the pages of his magazine.

The Playboy founder passed away Wednesday (September 27) at the age of 91, leading to an outpouring of celebrity reactions across social media. He leaves behind a legacy as a champion of sexual freedom, as well as civil and equal rights. But he was also a player on the small screen.

Yes, he became a hero to a new generation of fans with his E! reality series, The Girls Next Door, but he also oversaw the creation of The Playboy Channel (now Playboy TV) back in 1982 in the early days of cable TV, making him a visionary on the boob tube.

Hefner would also often play himself in a wide range of shows, whether animated or live-action. And he always brought a smile to viewers.

Take a look back at some of his more memorable guest appearances, below.

Family Guy

The Simpsons

Sex and the City

Entourage

Curb Your Enthusiasm

Laverne & Shirley

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