The Good, the Sad, and the Drugly
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The Good, the Sad and the Drugly is the seventeenth episode of season 20. It aired on April 19, 2009. It guest stars Anne Hathaway.
Synopsis
Bart volunteers at the Springfield Retirement Castle in order to impress Jenny, a girl who likes helping the world, but this leaves Milhouse (who took the rap for a school prank he and Bart pulled) less than impressed; Lisa becomes depressed when she writes a report on what Springfield will be like 50 years from now, but her medication makes her see everything happy - bright yellow happy faces, that is.
Plot
When Bart and Milhouse pull off a prank at Springfield Elementary, they unscrew everything in the building and watch as almost everything falls apart. Milhouse takes the fall and gets suspended from school. Homer forces Bart to sign in under Homer’s name and visit Grampa at his retirement home. Bart stays boring, until he sees a delightful 11-year-old volunteer named Jenny. He becomes smitten with her and, hoping to impress Jenny, Bart offers to volunteer at the home and fake being a good kid, just like Jenny.
Meanwhile, Lisa does a report on what Springfield will look like in 50 years and becomes very depressed at the dreary outlook. A concerned Marge takes Lisa to a psychiatrist who diagnoses Lisa with Environment-Related Despair and puts her on an antidepressant, Ignorital, to cure her eco-blues. However, the drugs make Lisa see almost everything as a smiley face, including homeless people, drunken people on the street and Chief Wiggum being shot.
At school, Bart tells Nelson he wants to ask Jenny for a date. Nelson gives Bart some chewing gum to help him doing so. Bart and Jenny go to the park for a picnic, where he tells here he helps a man with mental problems to impress her, who turns out to be Homer. They get on a boat and see Jimbo, Dolph and Kearney kicking a duck. Bart jumps to the lake and swims to the bullies in order to save the duck. They say they try to impress a girl named Shauna, so they have to punch Bart. Jenny gets very impressed for how Bart saved the duck. He ultimately invites her for a dinner at his home. Everything goes well until Milhouse appears to ask Bart why he didn't visit him, and soon discovers Bart is in love.
Looking for revenge, Milhouse follows Bart and Jenny everywhere to make Bart confess he is faking. At the Squidport, Milhouse shows Jenny a dolphin who is scared of Bart because he once made it swim in Seven Up. Bart can't stand it anymore and confesses to Jenny he was lying. She eventually breaks up with him, which makes Bart very sad. Meanwhile, Marge sees Lisa trying to kiss a fan (which looks like a smiley face for her), so she throws away Lisa's medicine (though Santa's Little Helper eats it).
At the Kwik-E-Mart, Lisa tells Bart that she realised that you can't hide your problems, and must face them head on. Bart agrees, and buys flowers to apologise. However, he apologises to Milhouse, because he has always been Bart's best friend. As a make-up prank, they ice the floors in Springfield Elementary, creating a massive ice rink.
