"Beware of Scorpio!
He'll sting you with his dreams of power and wealth!
Beware of Scorpio!
His twisted twin obsessions are his plot to rule the world and his employees' health!"
He'll sting you with his dreams of power and wealth!
Beware of Scorpio!
His twisted twin obsessions are his plot to rule the world and his employees' health!"
— Scorpio's Theme, "You Only Move Twice"
The Crapsack World of Springfield is home to some of the dimmest of dunces in all of Western Animation. Even so, The Simpsons is not afraid to churn out its fair share of excellent schemers that will have you shouting “Why you Magnificent little!” with their charm and wit!
All spoilers are unmarked. You Have Been Warned!
- "The Crepes of Wrath": Adil Hoxha is an Albanian spy working undercover as a foreign exchange student. After integrating himself into the Simpson family with his politeness and helpful attitude, he requests Homer to let him visit the Springfield Nuclear Power Plant, collecting information and successfully sending it to his home government. After being caught and outed as a spy by the FBI, he thanks the Simpsons for their hospitality and tells them not to let the experience sour their thoughts on the student exchange program.
- "Homer the Vigilante": Molloy is a resident of the Springfield Retirement Castle who moonlights as the Springfield Cat Burglar. When Homer, head of the new Neighbourhood Watch, was interviewed by Kent Brockman, Molloy phoned in to taunt Homer that he would steal the Springfield Museum's Zirconia and succeeds despite Homer's efforts. When arrested, Molloy gracefully returns all his stolen goods before being put in jail, where he tells Homer and Chief Wiggum about where he hid all his stolen loot, leading to the whole town hunting for it. When the location Molloy described is found, all that is present is a note saying Molloy lied and used the time they spent searching to escape. An archetypical Gentleman Thief, Molloy remains memorable despite his only appearance and relatively humble goals.
- "You Only Move Twice": Hank Scorpio is the president of the Globex Corporation whose passions include his employees' wellbeing, fun runs, and world domination. Threatening the UN with a Doomsday Device, Scorpio holds the world ransom while at the same time becoming friends with new hire Homer Simpson, actually managing to make Homer productive. Executing the escaping Mr. Bont after Homer tackles the agent and successfully repelling an attack on his lair, Scorpio amiably parts with Homer when the latter decides to return to Springfield for the sake of his family. Conquering the East Coast, Scorpio gives Homer the Denver Broncos as a farewell gift and assures him they will always be friends. Emulating the best aspects of the classic James Bond villains he parodies, Scorpio also cares just as much—if not more—about his employees' happiness than he does about conquering the world. The height of Affably Evil and perhaps the show's most successful villain, Hank Scorpio is a beloved character years after his single episode.
- "The Simpsons Spin-Off Showcase" — "Chief Wiggum P.I.": Charles "Big" Daddy is the local crime boss in New Orleans, who boasts the feat of stealing the Louisiana Governor's entire mansion and relocating it to a swamp to serve as his hideout. Feeling Chief Wiggum's new residency there is a threat to his activities, he becomes determined to drive Wiggum off, making his presence known by throwing a skull into Wiggum's office. When this fails to unnerve Wiggum, Big Daddy instead sends a 'warning alligator' into Wiggum's bedroom through the window. While Wiggum and Skinny Boy are preoccupied, Big Daddy sneaks inside and kidnaps Wiggum's son, Ralph, and holds him ransom to give Wiggum incentive to leave New Orleans. When he is spotted taking Ralph to the Mardi Gras festival, Big Daddy alludes Wiggum and Skinner who chase him to his hideout, where he makes one final escape by throwing Ralph at Wiggum as a distraction.
- "The Dad Who Knew Too Little": Dexter Colt is a shady Private Detective hired by Homer to investigate his own daughter Lisa. Colt compiles a detailed report on Lisa's life using several morally-dubious methods including: breaking into Lisa's locker, extorting Principal Skinner, and blackmailing Nelson. However, Homer refuses to pay Colt's outrageous bill, to which Colt pulls a gun on Homer before the latter escapes. Swearing revenge, Colt uses the intel he acquired about Lisa to frame her for the crime of kidnapping laboratory animals, forcing Homer and Lisa to be on the run from the law as fugitives. After finding the duo, Colt resumes his attempts at killing Homer, very nearly succeeding in taking the latter's life.
- "The Wandering Juvie": Gina Vendetti is a troubled pre-teen, who got into a juvenile correctional facility by shoving Snow White off a building. She easily manipulates Bart by tricking him into going along with her by playing a Wounded Gazelle Gambit, using her wits to outsmart the Warden of the facility and escape using a disco ball connected to a rope and a blacksmith to remove their cuffs. Despite constantly hurting Bart both mentally and physically, she truly loves him, and has no family to speak of and when caught she confesses everything get Bart set free. Troubled, and intelligent with a Hidden Heart of Gold, Gina showed herself to be among the most clever of Bart's girlfriends.
- "The Debarted": Donny is a troubled orphan from Shelbyville who quickly befriends Bart Simpson. Having been asked by Chalmers and Principal Skinner to infiltrate Bart's gang of friends, Donny takes the heat for one of Bart's pranks, tricks him into accusing Milhouse, and helps Skinner stay one step ahead of Bart at any given time. When Groundskeeper Willie sells Bart out, Donny has a Heel Realization and decides to stop Skinner and Chalmers. Troubled, calm, and a surprisingly good planner, Donny got the best of both Bart and Skinner.
- "The Book Job": Neil Gaiman, the King of Fantasy Books, is a Con Man who regularly heists his way to the top. Overhearing the main crew coming up with their book idea, Gaiman decides to steal it for himself and integrates himself into the group. Pretending to be a fool, Gaiman secretly strikes a deal with Moe the Bartender. When the publishing company changes their book to be about vampires, Gaiman plays on their pride of authorship, costing them their millions, and convinces them to swap the company's flash drive with one holding their original book. While Lisa is successful in swapping the flash drives, it is revealed that Gaiman had replaced theirs with one that gave him the credit, before escaping to Shelbyville and double-crossing Moe by poisoning him. Hammy, snarky, and smarter than he at first appears, Neil Gaiman is able to heist his way onto the bestseller list once again, despite not even being able to read.
- "The Great Phatsby": Jay G, born Jeremy Gilroy, is director of Golden Goose Records and a self-made billionaire who idolizes Mr. Burns and is determined to become as ruthless as he is. Originally a young thief who found Burns' book when he stole a bus, Jeremy become member of the Five Boyfriends quartet and threatened its composer Jazzy James into singing his profits to him. Jay G meets Burns when he and Homer crash his party, immediately befriending his idol and plotting to swindle him as written in the last chapter of his book. Jay G gives Burns the credit card created by the company he is CEO of and starts pushing old man to buy extravagant things and thrills until he goes broke and all his possessions are taken by Jay G to pay off the debt. He reveals his plot in his new number one rap song and redecorates Burns' power plant to buy the loyalty of his employees. When Burns tries to destroy his reputation by forming a rap group of people who want revenge on him, Jay G buys them and alongside rights to their song off, revealing it to Burns on the night of the group's debut. When Burns steals and tries to kill Goosius, the mascot of Jay's G brand and pet, Jay G decides to patch things up with Burns and give him his wealth back after everything turns out well.
- "Treehouse of Horror XXXIII" — "Death Tome": In this Affectionate Parody of Death Note, Lisa Simpson inherits all of Light's cunning while remaining legitimately well-intentioned. Upon finding Steve Johnson's Death Tome, Lisa sets about saving the world, first saving a cat from a criminal by causing said criminal to have a heart attack, before making Mr. Burns die in his sleep to stop his Global Warm plan. Next she kills all of Global Warm's employees in increasingly creative and unique ways. Lisa figures out that Bart is the mysterious "L" by recognizing his handwriting and then tricks Steve into letting his guard down so she can kill him and be free of the Death Tome when she realizes she has gone too far.
