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.
- Bowdlerization: Around the time Michael Jackson's death made the news, Channel 4 in the UK cut the part where Bart gets attacked by a street performer pretending to be The Jackson Five.
- 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!
- Creator Cameo: Showrunner Mike Scully voices the announcer at the magic show.
- 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!
- Genre Savvy: Ned instantly catches on to the Simpson males' attempt at trapping him in a Scamming the Bereaved scam because he saw Paper Moon, in which the characters use it often.
- 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.
- I Never Said It Was Poison: Parodied:
Blue-haired lawyer: Will you tell the court your whereabouts at the time of the carjacking?
Willie: I was alone in me Unabomber-style shack. I had nothing to do with the carjacking.
Blue-haired lawyer: Carjacking? Who said anything about a carjacking? (audience murmurs)
Willie: But didn't ya just say-
Blue-haired lawyer: I'll ask the question here, Carjacker Willie!"
- Kangaroo Court: Groundskeeper Willie's trial gets him rapidly convicted on only circumstantial evidence, and the judge allows Willie to be nicknamed "Carjacker Willie". The trial was a sham to make Homer and Bart confess, but for some reasonnote Willie was the only person in court aside from Homer and Bart not told about this—he even shot Principal Skinner, who faked his death.
- Kick the Dog:
- While most of Homer and Bart's cons are petty, trying to con Flanders using his dead wife was another level of low.
- Homer abandoning Bart at the beginning of the episode; and being angry with him, just because he did not make enough money and rightfully called him out for his Jerkass attitude was ridiculously petty.
- Lampshade Hanging: Homer is confused at the end of it that seemingly the entire town had nothing better to do than to teach him and Bart a lesson for some petty grifting.
- Latex Perfection: The judge in the trial is Grampa in disguise, who removes the mask when all is revealed.
- Never My Fault: In the original ending, after the trial was revealed to be a setup to get Homer and Bart to confess, they still manage to dodge responsibility:
People, thank you. This was a real wake up call... for my son. Bart:
Huh? Homer: (laughs)
That's right, boy! I was... in on it... too! Bart:
Oh, really? Then so was I. Homer:
? Well... I guess... that explains everything.
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)
Grandpa: That's right!
Bart: You don't smoke a pipe.
Grandpa: That's right! [coughs]
- Product Displacement: Like with the case of Chanel in "Scenes From the Class Struggle In Springfield", it's okay for Homer to say the name of the soda bottle he mistook for chloroform, but it's not okay to actually show the logo, which is partially obscured by Homer's fingers.
- 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".
- Oh, Crap!: After Ned starts to catch on to the Bible grift, Homer and Bart book it to the treehouse.
- 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 McMahon and declares Abe the winner of $10 million 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.
- The title is a play upon The Great Muppet Caper.
- Take That!: "Now, this little number was in The Sting Part II, so nobody knows about it!"
- Tempting Fate: At the Magic Palace's gift shop, Bart asks Homer if they can buy a magic kit. Homer responds, "Gee, I wish I could, son, but we've already left the gift shop," opening an exit door and escorting Bart out of it as he speaks. Unfortunately for Homer, they end up in a room labelled "Gift Shop Addition".
- Took a Level in Jerkass: Homer and Bart. While trying to get money to repair the car was understandable, the fact that they keep conning people after having already repaired the car (out of greed and possibly spite) is what makes them unsympathetic.
- Unwitting Pawn: After the truth comes out in the courtroom that the whole thing was to teach Homer and Bart a lesson:
Homer: I can't believe everyone was in on it.
Willie: WILLIE WASN'T!
- 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.