YMMV / The Simpsons S 21 E 10 Once Upon A Time In Springfield

• Harsher in Hindsight: The episode has a happy ending with Penelope choosing to stay with Krusty despite a (very well-merited) case of Insecure Love Interest on his part, but from subsequent episodes it's clear that the relationship didn't last.
• Hilarious in Hindsight:
  • Krusty mocks the idea of adding a princess character to the show to appeal to the young female demographic (at least until said princess character is revealed to be Krusty's biggest fan and they fall in love). Fast forward to "Bart vs Itchy and Scratchy", where Krusty spearheads an entirely female reboot of the titular Show Within a Show for the sake of profit.
  • Eartha Kitt makes a posthumous appearance in which she references her famous role as (the third) Catwoman on Batman (1966). Just two years later, Penelope's voice actress Anne Hathaway was cast as Catwoman in The Dark Knight Rises. So apparently, Krusty fell in love with Catwoman twice.