In this hour-long special, Mr. Burns ends up at odds with Jay G, a music mogul who models his business practices after Burns', to the point of conning him out of his riches and possessions.
Tropes:
- Alliterative Name: Blake Black.
- Bite of Affection: As they're leaving Lengthy Island, Homer is sad because he already misses Jay's goose Goosius, a Foul Waterfowl who was constantly nipping him. In response, Bart bites Homer's arm without warning. Homer is touched and the two share a fond look.
- Borrowed Catchphrase: In Jay G's Villain Song and Diss Track aimed at Burns:Now watch me as my fingers tent,'Cause I own you, it is excellent
- Chekhov's Gunman: By the time Smithers returns with the ice ordered by Mr. Burns, it has already melted and serves to cushion Burns and Jay G's fall.
- Lampshaded. Homer mentions via voiceover that the scented candle salesman, later revealed to be Jazzy James, will return later in the plot. When he does, Homer points this out via another voiceover.
- Conspicuous Consumption: Burns' wealthy opposite number Jay G. shows him how to "splash the cash" in what proves a highly effective ploy to drain his bank account and take everything he owns.
- Corrupt Corporate Executive: Under the false pretense of wanting to thank the man who inspired him, Jay G tricks Mr. Burns into spending the latter's fortune in stores owned by him.
- Description Cut: During the party, Mr. Burns realizes Smithers didn't bring ice and assumes the latter is having fun somewhere. It turns out he's crossing a dangerous river.
- Everyone Has Standards: Principle Skinner freely admits that for someone like him to call Mr Burns party boring he must have done something wrong.
- Evil Mentor: Mr Burns is absolutely trilled to find out he was this for Jay G.
- Foul Waterfowl: "Goosius," Jay G's beloved pet goose and the mascot for his record label. Homer takes a shine to him despite his constant and vicious attacks.
- Friendly Enemy:
- Despite everything, Homer feels a sense of loyalty to Burns and can't bring himself to keep working at the nuclear plant after it falls into Jay G's hands, instead scheming with Burns to get his money back.
- Burns finally feels fulfilled when he realizes that Jay G turned on him because Burns' own writing influenced him to be ruthless, realizing that as long as his life can inspire such evil he has a legacy.
- Funny Background Event: The graves at the Burns family mausoleum.
- Hoist by His Own Petard: Jay G reveals that he double-crossed Mr. Burns because the last chapter in the latter's book tells people to do it to whoever inspired them. Subverted because knowing this makes Mr. Burns' glad that his evil will live through Jay G.
- Hypocritical Humor: Not wanting store-bought ice for his party, Mr. Burns tells Smithers to bring ice from a Canadian river. However, when Smithers asks how the ice is to be wrapped, Mr. Burns says it doesn't matter because ice is ice.
- Improvised Clothes: Moe rented a suit for Burns' party... then Xeroxed it and wore the paper copy instead.
- Intergenerational Friendship: Burns and Jay G. represent two very different (and distant) generations of wealthy businessman, with Burns being an uptight miser while Jay G is a mid-2010's rapper whose lifestyle is rife with Conspicuous Consumption.Homer: And so was forged the most unlikely of friendships: a man who discovered Rick Ross and a man who dated Betsy Ross.
- Literal Metaphor: Burns attempts to get back at Jay by literally "cooking his goose"—that is, Goosius, his beloved Animal Companion and record label mascot.
- Mythology Gag: When asked to throw out all of Mr. Burns's prized possessions, Homer threw out Bobo, Mr. Burns's favorite stuffed bear.
- An Offer You Can't Refuse: When even Mr. Burns' hounds change their loyalties to Jay G, the latter threatens to sic them on Burns unless he signs them over to Jay.
- Person as Verb: In his Villain Song, Jay G taunts Burns with the fact that "there's no one doing [his] Smitherin'."
- Screw the Rules, I Have Money!: A rich boy is allowed to cut lines in a fancy neighborhood because his Dad is the richest Dad there.
- The Scrooge:
- Mr. Burns' party fails because he spared every possible expense. Jay G. shows him how much happier he can be with all of his wealth by turning him on to Conspicuous Consumption...all part of a plot to bankrupt him.
- Moe borrowed a suit, Xeroxed it and wore the copy to the party. Even he thinks Burns is too cheap.
- As a parody of the Trope Namer, Mr. Burns has a deceased ancestor named Ebenezer, whose epitaph states the ghosts taught him nothing.
- Self-Made Man: Jay G claims to have been a lowlife until he got inspiration from a book written by Mr. Burns.
- Shoddy Shindig: Determined to revive the Gatsbylike status he had as a young man, Burns gets Smithers to invite his friends to a party at his summer home in the "Springfield Hamptons." Burns being low on living friends, Smithers just passes the invites to Homer and tells him to invite whoever he wants. Everyone shows up anticipating the kind of lavish affair you'd expect given Burns' money, but with Smithers held up on a lengthy errand to fetch ice from Canada, Burns has cheaped out on the party big-time, offering off-brand Ritz crackers and piles of salt as appetizers, hiring a "band" consisting of two elderly wind instrumentalists and forcing his guests to wear protective booties so they don't scuff the dance floor.
- Shout-Out:
- While bragging about cheating Mr. Burns out of his fortune, Jay G compares himself to Slytherin and Burns to Hufflepuff.
- One of Burns' ancestors is named Ebenezer. The epitaph reads "The ghosts didn't change him".
- The subplot of Smithers getting lost delivering ice to Burns' party spoofs The Revenant.
- The hate song against Jay G mentions Gollum and his "precious".
- All people invited to Mr. Burns' party are either dead or fictional. As an example, Smithers shows Homer an invitation addressed to Mr. and Mrs. Popeye T. Sailorman.
- Upon first noticing Jay G's party, Burns uses "Great Gatsby" as an exclamation.
- Status Quo Is God: Mr. Burns gets the plant back and the only thing left from how Jay G changed it is something Burns says it'll no longer happen tomorrow.
- Tempting Fate: Homer says it can't be too tiring to take Mr. Burns to the other side of a lake by rowboat. He's wrong.
- Whole-Plot Reference: To The Great Gatsby, specifically the Baz Luhrmann film version, with a bit of Empire thrown in.
- Villain Song: Jay G performs "CEO of Obsidian" (also called "Monty Burnt")
, a rap where he gloats his betrayal of Mr. Burns by tricking him into bankrupting himself and taking everything he owns.
