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.
