By Christopher Rosen
September 28, 2017 at 12:25 AM EDT

Legendary Playboy founder Hugh Hefner died on Wednesday at the age of 91, leaving behind a publishing legacy nearly unmatched in the last 50 years.

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” Hefner’s son Cooper, chief creative officer of Playboy Enterprises, said in a statement. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history.”

With Hefner at the helm, Playboy became one of the most recognizable magazine brands ever — and the company’s success allowed the man known as “Hef” to find himself firmly ensconced in the zeitgeist. Rarely was that more evident than on television, especially during the ’90s and ’00s, where Hefner appeared on numerous shows as himself, including Roseanne, Blossom, The Larry Sanders Show, The Bernie Mac Show, and Las Vegas, not to mention his E! reality series, Girls Next Door.

Ahead, five of Hefner’s most memorable scripted television appearances … as himself.

Hugh Hefner on The Simpsons (1993)

Hugh Hefner on Sex and the City (2000)

Hugh Hefner on Entourage (2005)

Hugh Hefner on Curb Your Enthusiasm (2005)

Hugh Hefner on Family Guy (2007)