The Simpsons season 23 episode 8
Episode title: 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 Krusty's first agent and former girlfriend.