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.

          The Simpsons Villains

Springfield Republican Party
Mr. Burns | Waylon Smithers | Blue-Haired Lawyer | Birch Barlow | Lindsey Naegle

Terwilliger Family
Robert Terwilliger Jr. | Cecil Terwilliger | Francesca Terwilliger | Gino Terwilliger | Robert Terwilliger Sr. | Dame Judith Underdunk

Springfield Mafia
Fat Tony | Fit Tony

Environmental Protection Agency
Russ Cargill

Recurring Characters
Itchy| Space Mutants | Patty & Selma Bouvier | Herman Hermann | Nelson Muntz | Jebidiah Springfield | Jimbo Jones | Dolph Starbeam | Kearney Zzyzwicz | Agnes Skinner | God | Jessica Lovejoy | Artie Ziff | Baby Gerald | Wainwright Montgomery Burns | Snake Jailbird | Senator Mendoza | Matt Groening | Constance Harm

Treehouse of Horror
Kang & Kodos | Killer Krusty Doll | Zombies | Ned Flanders | The Devil | Gremlin | Count Burns | Seymour Skinner | Lard Lad | Groundskeeper Willie | Hugo Simpson II | Bart (Fly) | Witch Marge | The Collector | Killer Toupée | King Snorky | Homer's Clones | Billy the Kid | Jonathan Frink Sr. | Muttonchop Murderer | The Blob | The Grand Pumpkin

Guest Star Characters
Black Weasel | Cesar & Ugolín | Adil Hoxha | Lucille Botzcowski | Professor Werner Von Brawn | Bob Arnold | Lyle Lanley | Kindergarten Teacher | Adolf Hitler | Robotic Richard Simmons | The Leader | Movementarians | Francine Rhenquist | Hank Scorpio | Miss Goodthighs | Molloy | Rex Banner | Dexter Colt | The Jockeys | Hell's Satans | Jack Crowley | Cooder & Spud | French Chef | Jim Hope | Larry Kidkill | Howard K. Duff VIII | White Dog | Frank Grimes, Jr. | Captain Mordecai Barrows | Clownface | Simon Cowell | Officer Krackney | Shadow Knight | Baby Button Eyes | Stanley DeGroot | Will Wright | Stubborn Ape | Mr. Dirt | Sparklemon | William Shakespeare | Julia | Andy Hamilton | Devan & Quenley Woosterfield | Comic Book Guy (Brick Like Me) | Bart Simpson's Creatures | Mav & Portia | Blue-Eyed Man | Nigel Bakerbutcher