Grandpa teaches Homer and Bart how to be con artists while Marge gets smashed on Long Island Iced Teas.
- Abusive Parents: Homer abandons Bart at the wharf at night after his magic act only earns 60 cents. Bart doesn't really hold it against him, though.
- All Part of the Show: Subverted when Marge is attacked by the monkeys in the magic act:Announcer: Folks, this is not part of the act. Please help her.
- Brutal Honesty:Homer: A good son would come through for his dad!
Bart: And a good dad wouldn't miss his son's little league games!
Homer: I told you: I find them boring!
- Captain Obvious: Marge's reaction when Homer and Bart lie to her and Lisa about the church carjacker:Bart: And he said if we went to the cops, he'd come back for Maggie.
Marge: (gasps) Oh dear, we don't want that!
- Foreshadowing: In retrospect, Grampa easily getting away on a motorized cart without any pursuit from the "FBI agent" should've been a clue that Grampa was in on the con.
- Gainax Ending: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!
- Getting Crap Past the Radar: When Bart does some magic, Homer tells Ned to pony up: "The kid's not turnin' tricks for free." "Turning tricks" is slang for a prostitute having sex with a client.
- Giant Novelty Check: Homer, Bart and Grandpa use one as part of the scam they pull on Abe's fellow residents at the retirement castle.
- Kangaroo Court: 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.
- Latex Perfection: The judge in the trial is Grampa in disguise, who removes the mask when all is revealed.
- Non-Answer:Marge: Why are you frosting that old throw pillow?
Homer: I could ask you the very same question.
- Not Helping Your Case: When Willie is grilled on the stand:Willie: I was alone in me Unabomber-style shack.
- Of Course I Smoke: 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]
- Pun: When Homer wants to "scare Bart straight" by requesting Wiggum put him in a jail cell:Wiggum: I'll put you in the Rick James suite. It's "super-freaky".
- Riddle for the Ages: Why would so many people (including special guest star Edward Norton) go that far just to teach Homer and Bart a lesson?
- Saw It in a Movie Once: 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.
- Shout-Out: In one grifting scheme, Homer poses as Ed Mc Mahon 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.
- Kent Brockman ends his pay phone call with: "Good night, and have a pleasant tomorrow."
- Homer and Bart try to con Ned by selling him a Bible with his name on it, but Ned says, "Wait a minute, this seems an awful lot like that movie Paper Moon."
- Devon Bradley is currently performing in Joseph and the Amazing Technicolor Dreamcoat at the dinner theatre.
- Take That: "Now, this little number was in The Sting Part II, so nobody knows about it!"
- Wrote the Book: Abe claims he wrote the book on grifting. Bart checks the grifting book he had been carrying and sees Abe's name.