The Fresh Prince of Bel-Air: Season 4, Episode 9

4 - 9: Fresh Prince After Dark

When Jackie finally agrees to go on a date with Will, he reluctantly has to cancel when Hilary asks him to be her chaperone at the Playboy Mansion, where she is asked to pose in an upcoming issue. Upon learning of Hilary's opportunity, Uncle Phil forbids her from posing for the magazine. However, when he learns that she decides to go with it, Uncle Phil decides to go into hiding.