The Simpsons go on a late-night attic search after Bart and Lisa (who are freaked out over a horror movie Homer let them watch) begin hearing voices—and find Marge's ex-prom date Artie Ziff, who's on the run for cheating the shareholders of his company.
- 0% Approval Rating: Artie. Everyone in the courtroom galleries during the trial is glaring at him, well aware of what he did to Homer.
- Bad "Bad Acting": Lenny's performance in the horror movie's.
- Bolivian Army Ending: The final scene of the episode is Artie pissing off all of the inmates at the prison by squirting water in their faces and extinguishing their cigarettes. Marge makes it pretty clear that she doesn't expects Ziff to survive the beatdown to come.Marge: Children, it may be the last time we see "Uncle Artie".
- Continuity Nod: Llewellyn Sinclair, Professor Lombardo, Aristotle Amadopolis and Jay Sherman, all characters previously voiced by Lovitz, appear at Moe's.All: Hello, handsome!
Artie: Hello... losers.
- Corrupt Corporate Executive: Ziff. He runs his company into the ground (although in his defense it was mostly the dot-com bubble bursting) and then manages to swindle Homer into becoming CEO so the IRS will arrest him instead of Artie.
- Everything Is Racist:Marge: My husband's going to jail and it's all your fault! Do you know why no one likes you?
- Eye Scream: Continuing a Running Gag with Lenny, his movie character loses his eyes to an evil doll.Lenny: The buttons look like they're sewn to my eyes, but they're really held on with hot wax.
- Hilariously Abusive Childhood: When in prison, Homer admits that he enjoys strangling Bart, and starts to cry from the fact that Bart will be an adult when his father is out, too old to be chocked.
- House Squatting: After hearing weird sounds on the attic, the Simpsons go check and find out that Artie has been living inside of the house without their knowledge for months, surviving by feeding off the attic's mold.
- Informed Judaism: The only time thoughout all of his appearances in which we obtain information that Artie Ziff is Jewish is his blunt Comically Missing the Point question of "antijudaism?" when Marge asks him if he knows why everybody hates him as a preface to a "The Reason You Suck" Speech.
- It's All About Me: Artie Ziff before Marge called him out on that.
- Heel Realization: His reaction afterward.
- Artie Ziff. He breaks into Homer and Marge's house, squats in their attic and tricks Homer into becoming majority shareholder of ZiffCorp so he'll be arrested for Artie's crimes. And once in prison, he sprays water into the faces of fellow inmates to put out their cigarettes (because of all the hazards of smoking, you see).... that is something that would be enraging even if not done to a convicted felon (and it's made pretty clear that he is about to be killed before the credits start running).
- Patty and Selma, but what else is new? When they find out that Artie got Homer thrown in jail, Selma has sex with Artie to celebrate.
- The Last Straw: When the Simpsons suddenly hear theremin music coming from the attic:Homer: That's it. It's one thing for a ghost to terrorize my children, but quite another for him to play my theremin.
- Majority-Share Dictator: Played with. Ziff, having absolutely nothing else to his name, bets the company stock he owns in a poker game, which Homer wins. Then at that moment the IRS barge into the Simpson house looking for the CEO of Ziff Co... which at the time technically is Homer. He ends up being taken away with Artie (the man who actually founded, ran, and then destroyed the company) remaining untouched.
- Missing Steps Plan: The moment Artie Ziff told the Simpsons he was a dot-com billionaire, they already understood how he went broke.
- Recognition Failure: Homer, believing that he's been in jail for years instead of a few weeks at most, thinks Lisa is a preteen Maggie, and Artie is a grown-up Bart.
- Riches to Rags: Artie after the bubble burst.
- Short Film: An in-universe example happens with The Wild Dingleberries Movie, where the runtime is shown as 47 minutes.
- Skewed Priorities: Lisa drops her camera and runs away from the odd noises in the attic, which for all she knows is something very, very dangerous, and takes a moment to go back to where the camera is lying down and rattle off her home film's copyright legalese before continuing to run away (without the camera).
- Stalker with a Crush: Artie's this to Marge. After the family finds out that he's been living in their attic since he went broke, he explains that he did it because Marge is the closest thing he's ever had to true love—but Marge is quick to point out that she and Artie only had one date together and that he almost raped her on the night of their high school prom.
- Take That!:
- With The Wild Dingleberries Movie, to a very tumultuous time in American animation and the industry that is woefully underdocumented and mentioned, but does exist: Where big time animation giants Disney and Nickelodeon were milking in house cartoon shows to make onto the cinema big screen for an extra helping of profit, and essentially killed off any major movie interest in 2D animation for a good decade. While Nickelodeon did start this trend, the instigating feature of The Rugrats Movie and even the parodied The Wild Thornberries Movie were at least well made for the big screen; only Hey Arnold! The Movie (Craig Barlett is Matt Groening's cousin, so some favoritism might have been involved) and all of the flak The Simpsons gives to Disney would have been more appropriate, as they were playing the dueling train far much worse.
- Technology Marches On: Acknowledged In-Universe. Ziff only gets as far in the story of how he became poor as to mention his business was a dot-com company before everybody interrupts him by saying "we get it".
- Too Dumb to Live: Artie didn't realize how his fellow inmates thought about his plan to save them from smoking.
- Wrongful Accusation Insurance: After Homer is released, the guard says to make it up to him, he's allowed to either steal a car or punch him in the stomach. Homer chooses the latter, which the guard moans every wrongfully arrested prisoner chooses.