Andy Hamilton

"He was like "turn left" and "turn right" and "do this" and I was like "I quit, man." But on the way back I got THIS. Check it out: it's a fly in an ice cube!"

- Andy Hamilton

Andy Hamilton is the former bully of Springfield Elementary and one of the school's greatest pranksters. He was there before Bart's time, and he is roughly about nineteen or so in the episode. Andy attended school way back when Principal Skinner was a laid-back, relaxed, "cool" principal, and he encouraged students to do whatever they wanted. Principal Skinner was so likeable he even made Willie the Swimteacher rather than Groundskeeper as he would later be. Principal Skinner's attitude completely changed, however, when a dark figure (Andy in shadow) crept over the swimming pool and filled it with worms one day. Later, Skinner went for a swim and plunged right into the worm-infested pool, and Hamilton closed the pool and left Skinner in there for a day with the worms.

When Skinner came out, he was traumatized, because his already bad Post Traumatic disorder from the Vietnam War had left him already scarred and this humiliation was the final straw. Andy was inadvertently responsible for Willie being demoted, and Skinner was so terrified of Andy he refused to speak even his gender. Bart asked who it was, and Skinner said "He?" sarcastically, to which Bart gasped, "It's a she?" to which Skinner said "Just kidding, it's a boy." The two fell about laughing until Skinner said he'd told enough already.

Willie ended up telling Bart all he knew, and so Bart and Milhouse went to meet Andy Hamilton, who turned out to be pretty much the world's greatest loser: He lived at home and did nothing when his mother went to work all day, he didn't even do housework, he watched movies and TV all day, and he spent his time thinking of more evil pranks. Andy had a poisonous cobra in his house, and it bit Milhouse, Andy not caring about anything.

Bart promised he'd get Andy work because he seemed to be shocked by Andy's condition when Lisa said he sounded like a loser. Bart was initially impressed by Andy, and wanted to live like him, but then Lisa mocked Andy as a loser. So Bart decided to get Andy a job with Krusty the Clown, who got annoyed by Andy, and Andy quit. So, Bart got him another job, but suddenly, in a complete change of events, Andy ended up being screenwriter for Krusty. He also had a girlfriend, all of a sudden.