Grandpa teaches Homer and Bart how to be con artists while Marge gets smashed on Long Island Iced Teas.

!! Tropes:

* GainaxEnding:
-->'''Homer:''' Wait a minute, you're telling me the police force, the TV news, a courthouse full of people, and a popular entertainer had nothing better to do than to teach me and Bart a lesson?
-->'''Lisa:''' I know it seems farfetched, even insulting to your intelligence, but there's a simple and highly satisfying explanation. You see...
-->'''Otto:''' ''(interrupting)'' Hey everybody, surf's up!
* GiantNoveltyCheck: Homer, Bart and Grandpa use one as part of the scam they pull on Abe's fellow residents at the retirement castle.
* KangarooCourt: Groundskeeper Willie's trial. Willie was the only person in court aside from Homer and Bart who didn't know the trial was a sham to make Homer and Bart confess. He even shot Principal Skinner, who faked his death.
* OfCourseISmoke: After failing to con Flanders, Homer and Bart hide in the treehouse, where Grandpa is waiting for them in a dark corner with a pipe.
-->'''Grandpa:''' Amateurs! ''[lights up]''
-->'''Homer:''' Dad?!
-->'''Grandpa:''' That's right!
-->'''Bart:''' You don't smoke a pipe.
-->'''Grandpa:''' That's right! ''[coughs]''
* RiddleForTheAges: Why ''would'' so many people (including special guest star Edward Norton) go that far just to teach Homer and Bart a lesson?
* SawItInAMovieOnce: Homer and Bart try a scam they saw in a movie but it backfires when their target recognises the scenario. Grandpa Simpson's scam also comes from a movie but one no-one watched so no one catches on.
* ShoutOut: In one grifting scheme, Homer poses as Creator/EdMcMahon and declares Abe the winner of $10,000,000 from "that Publisher's Clearing Dealie".
** Grampa's line about being rich enough to afford a "crazy, stripper wife" is a reference to Anna Nicole Smith and her marriage to J. Howard Marshall, which a lot of people believed was so Smith could get his money when he died.
* WroteTheBook: Abe claims he wrote the book on grifting. Bart checks the grifting book he had been carrying and sees Abe's name.