||Once Upon a Time in Springfield
"Once Upon a Time in Springfield" is the tenth episode of Season 21 (originally going to be the final episode of Season 20).
Krusty is forced to add a female character named Princess Penelope to his show in order to attract more female viewers. She immediately overshadows Krusty as the ratings improve. Bart and Milhouse want to get the show back to the way it was, but the situation gets more complicated when Krusty and Penelope fall in love and decide to get married. Meanwhile, Homer, Lenny and Carl consider working at a competing nuclear plant when Mr. Burns cuts off their daily doughnut service.
After performing a routine episode of his show, Krusty is approached by two network executives who tell him they want to make some big changes in order to increase his popularity among girls. Krusty initially refuses, but after the executives threaten to replace him with a reality show (based around finding a new Krusty), he frantically agrees.
In the following day's episode, he introduces Princess Penelope, an ultra-feminine princess character who sings syrupy songs and dances around an all-pink, Disney-esque set, complete with a unicorn. Young girls like Lisa are quickly captivated by Penelope, but boys like Bart and Milhouse are repulsed by this dramatic change to their favorite show.
In short time, Princess Penelope's popularity grows to stratospheric levels, quickly eclipsing Krusty himself. After being persuaded by Bart to reclaim his show, Krusty confronts Penelope — who off camera, is a plain-spoken Jersey girl — in her dressing room, intending to fire her from the show. Penelope preemptively confesses her love for him, however, revealing that she's had a crush on the clown since childhood. Krusty is immediately smitten, and the two begin dating.
Meanwhile, Marge gets a deep fryer and starts making homemade donuts. Homer, however, refuses her treats, claiming he is more than satisfied with the donuts at work. Upon arriving at the Power Plant, however, he is shocked to discover Mr Burns has slashed donuts from the office budget. Dejected, Homer, Lenny and Carl decide to go drinking at Moe's Tavern. There, they meet a professional head hunter who's looking for new nuclear engineers to work at the Capital City plant. After a tour of the plant, which is vastly better than their own, they decide to quit. Mr. Burns, however, manages to convince them to stay by promising them expensive, delicious donuts made of impossibly rare and exotic ingredients.
Meanwhile, Krusty and Princess Penelope's relationship has grown deeper. Their entire show soon becomes little more than the two co-stars engaging in sappy on-screen kissy-poo antics, climaxing with Krusty making an on-air proposal. Believing the Krusty they know and love is slipping away, Bart and Milhouse plot to stop the wedding.
At Krusty's traditional Jewish wedding (presided over by Krusty's father, the Rabbi Krustofsky), the boys attempt to scare Penelope off by highlighting some of Krusty's previous failed marriages (Krusty, we learn, has been married 15 times before). It works, but not the way the boys expect — Krusty realizes that while his ex-wives were all as flawed as he is, Penelope is a genuinely good person who deserves someone better. She takes it amiably, kissing him before she leaves.
Days later, we see a lovelorn Penelope entertaining strangers in Paris. She goes to a nearby bridge, looking down at the water of the Seine River. A boat passes by, and she sees Krusty's reflection in the water. She turns around, expecting to see him, only to see nothing. Krusty is actually there, though; he was just in the water, having fallen off the boat. She flings herself in the water, and the two float down the Seine, staying afloat with Penelope's wooden guitar's case.
- Anne Hathaway won an Emmy for her performance as Princess Penelope.