The Good, the Sad, and the Drugly

Anne Hathaway as Jenny

"The Good, the Sad and the Drugly" is the seventeenth episode of the twentieth season of the animated television series The Simpsons, and the 437th episode overall. It originally aired on the Fox network in the United States on April 19, 2009. In the episode, Bart sets up Milhouse to take the fall for a prank the two of them pulled, and the duo's friendship becomes strained when Bart falls for a charitable girl named Jenny. He starts making her think he is actually good and not bad. Meanwhile, Lisa goes insane when she finds articles on the Internet predicting that Springfield will be a barren wasteland in fifty years.

The episode was written by Marc Wilmore and directed by Rob Oliver. It features actress Anne Hathaway as Jenny. "The Good, the Sad and the Drugly" received generally mixed reviews from critics for its similarities with other episodes. According to the Nielsen ratings, the episode was watched by 6.50 million households in its original airing.

Milhouse and Bart loosen every bolt and screw in Springfield Elementary, leading to mass chaos when the building and its contents fall apart. Milhouse is apprehended by Principal Skinner, is suspended from school for a week (and subsequently grounded). Bart, whose involvement with the prank was not discovered, promises to visit Milhouse every day. Homer drops Bart off at Springfield Retirement Castle to visit Grandpa. There, Bart is immediately smitten with a kind and charitable girl named Jenny. Bart makes a concerted effort to appear "good" to Jenny, demonstrating his newfound good nature by defending ducklings and eventually inviting Jenny over for dinner. However, Milhouse shows up on the Simpsons' doorstep and threatens to reveal Bart's true, dark nature because Bart forgot to visit him during his suspension. Milhouse begins appearing on Bart and Jenny's outings, each time hinting at Bart's misdeeds. Eventually, Bart confesses to Jenny that he was actually bad before he met her and only pretended to be good to start a relationship. He continues to say that he is changed completely because of being with her. Jenny, though momentarily pleased by Bart's honesty, realizes she cannot forgive or trust Bart, and angrily dumps him. At home, Bart cries, and Homer & Marge console and reassure him that girls come and go, but he still has his family, only for him to cry even harder, and for Homer to shed tears too.