Brush with Greatness

"Brush with Greatness" is the 18th episode from the second season of The Simpsons. The episode aired on April 11, 1991.

Synopsis
After Bart and Lisa see Krusty do his show at the Mt. Splashmore water park, they ask Homer if they can go there. Homer gets annoyed, but reluctantly decides to take them there. The family goes to Mt. Splashmore, where they ride H2WHOA!, a crowded water slide. As Homer goes on H2WHOA!, he gets lodged in a section of a pipe. After the rescue crew removes him from the ride, with the help of a large crane, he realizes that he needs to lose weight and announces that he will go on a diet.

While Homer is looking for his weights, Bart stumbles on paintings of Ringo Starr that Marge made as a student in high school, when she had a crush on him. Lisa asks Marge what her painting talent was as a schoolgirl, and she says that as a high school student, she was scolded for doing a painting of Ringo Starr. She also recalls sending a painting to him for an "honest opinion", which she also recalls never actually got a response. Lisa suggests that Marge take a painting class at Springfield Community College, which she does. She makes a painting of Homer, which her professor, Lombardo, praises. It wins the college art show.

Mr. Burns wants Marge to paint his portrait for the Burns Wing of the Springfield Art Museum. She reluctantly agrees, as long as Burns insists that the painting portray him as a beautiful man. While Burns heckles Marge as she does the painting, Homer finds out that he weighs 239 pounds, which is 21 less than what it previously was. After Burns insults Homer, Marge insists that he leave the house and is ready to quit until Homer encourages Marge to finish the painting and she gets a reply from Ringo Starr, who is decades behind on answering his fanmail, praising her artwork. She finishes the painting, and at the opening of the Burns Wing, she unveils the painting. The painting depicts a naked, frail, and weak Burns. The people are shocked, until Marge explains that it depicts what Burns actually is: a vulnerable human being which will, one day, be no more. Everyone, even Burns, who is at first outraged but then accepts his new glory, praises Marge's painting.