At the Springfield Lemon Tree, after Bart mentions that Springfield is a nice place to live in, Shelby immediately remarks that Springfield sucks. After in an exchange of insults between the Springfield boy and the Shelbyville boys, Shelby and his gang try to steal their lemons, only to be pelted by them in return. Shelby vows to get back at them and steals their lemon tree.
When Bart tries to retrieve the lemon tree by going incognito, the Shelbyville boys put him to the test by making him spray paint "Springfield Sucks" on top of the Shelbyville Bluffs. After first, Bart spray paints what he tells him, but he actually paints "Springfield Rules Suckers", and reveals himself to the boys. Before Shelby and his gang can beat him up, Bart's distracts them by telling them there's an attractive cousin. After Bart swipes one of the Shelbyville children's skateboard to make a getaway, Shelby proceeds on his skateboard to catch him, leading to an all-out chase around Shelbyville.
While Bart accidentally hides out in the Tiger Feeding Area at the Shelbyville Zoo, Shelby and his gang almost catch up to him, before Bart picks the right door to escape through. Later on, Shelby is later seen making lemonade, while his friends ride motorbikes around the lemon tree. Shelby is last seen helping his father close the impound lot gate to prevent the Springfield boys and their fathers from getting away with the lemon tree tied on top of Ned Flanders' RV, only for them to shake their fists in anger as they get away.
Comparison to Bart Simpson
He looks similar to Bart, with the exception of his hair, his pants, and the color of his hat, he bears some resemblance to his Springfieldian counterpart. He also has a best friend named Milhouse and a similarly dim-witted, balding father like Homer. He is arguably smarter than Bart as evidenced by his quote, "You just got citric acid in my eye!" However, he falls short in the name-calling department, having been handily out-insulted by Bart in the first encounter near the lemon tree.
- Episode – "Lemon of Troy"
- Comic book – Batter-Up Bart
- Book – The Simpsons: A Complete Guide to Our Favorite Family
- Book – Chief Wiggum's Book of Crime and Punishment
- He was not given a name in the episode, but was named "Shelby" in The Simpsons: A Complete Guide to Our Favorite Family.
- Shelby owns a guard dog, similar to many of Mr. Burns hounds.
- In the Bart Simpson comic book series, Shelby is part of a little baseball team called the Shelbyville Raptors.
- Shelby has a tattoo that says "destroy" on his right arm.
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