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Andy Hamilton is a well-known former pupil and prankster at Springfield Elementary School. He lost his pranking attitude and became a writer for Krusty the Clown. Bart Simpson saved Andy's pranking career by telling him that he had to grow up.

Andy's most famous prank was when Andy was a student at Springfield Elementary, and Seymour Skinner loved to swim in the school's early swimming pool (revealed by Groundskeeper Willie). Andy filled the pool with worms and locked Skinner in the pool for a whole weekend, including Monday, a teacher's holiday. The prank was named "Night of the Wigglers".

Later, Bart and Milhouse met Andy and learnt that he was unemployed and lived with his mother. Bart got Andy a job as Krusty's advisor, but quit after his first day because Krusty was bossing him around. Andy later got rehired by Krusty, but Bart was worried when he saw a worm truck driving into the studio...