The Simpsons - Season 23 Episode 8
The Ten-Per-Cent Solution

Krusty the Clown becomes depressed after getting fired from his television show for being unpopular with children. The Simpson family encourages him to make a comeback, suggesting that he seek help from an agent they met earlier at a television museum. This agent turns out to be Annie Dubinsky, who was Krustys first agent and former girlfriend.