With the family in dire straits once again, Homer decides to ask Mr. Burns for a raise, but Burns has a better plan: hire Homer as his personal jester (or "prank monkey") while Smithers takes time off to go to New Mexico to star in a musical he wrote about Malibu Stacy. But when the pranks escalate to being gross and humiliating, Homer must choose between making money for his family or retaining his dignity.
"Homer vs. Dignity" contains examples of:
- Bad Santa: Burns tries to pay Homer to act as one in the parade, throwing fish guts onto the crowd. Homer refuses and Burns takes up the role himself.
- Bait-and-Switch Comment: When Bart was telling how he got his "A", how many viewers thought he'd say he blackmailed Principal Skinner and Mrs. Krabappel (since he did it before on "Grade School Confidential")?
- Black Comedy Rape: The infamous "panda scene". It should be noted that it thankfully occurs off-screen.
- Broke Episode: The Simpsons are broke. Homer's poor health makes him uninsurable and he's too stupid not to blow any money he gets. He's bluntly told by a financial planner he needs more money.
- Christmas Episode: Near the end of the episode.
- Comically Missing the Point: When Lindsey Naegle shows Homer and Marge a simulation of the family becoming poor and wrecked. Homer remarks "Marge, your posture looks terrible".
- Disproportionate Retribution: Homer imagines himself siccing a black leopard onto a creditor to get out of paying one dollar.
- Even Evil Has Standards: Burns pays Homer to throw pudding into Lenny's eyes despite Homer's protests that Lenny's a war hero. Both laugh at Lenny's misfortune and Burns takes more sadistic pleasure when Homer throws another pudding dessert into Lenny's other eye. But when Homer hits Carl in the eyes with pudding, Burns is appalled.Mr. Burns: What are you doing, man? That's Carl!
- Riddle for the Ages: Which standards was Burns upholding in this case?
- Eye Scream: Pudding and fish guts being thrown into Lenny's eyes
- For the Evulz/For the Lulz: Burns paying Homer to make a fool out of himself.
- Gilligan Cut: When Homer tauntingly asks what the restaurant is going to make the Simpsons' do to pay for the meal, make them work it off as a mariachi band, it cuts to do them doing just that.
- Have a Gay Old Time: Mr. Burns deems his "prank monkey" more amusing than Smithers and says the latter doesn't know the meaning of "gay".
- Insistent Terminology: Lindsey Neagle is a financial planner, not a financial consultant.
- It Will Never Catch On: Mr. Burns laughs off Smithers' play about Malibu Stacey, sarcastically saying he should write a musical about the common cat or the King of Siam.
- Kick the Dog: A whole episode-ful.
- Kill the Poor: When Homer wonders what to do with his dirty money, Lisa comments there're poor kids. Thinking she wants them gone, Homer says he's buying a weapon.
- Mondegreen: At the beginning, Homer mishears "financial planner" as "financial panther" and has an Imagine Spot of siccing a black leopard onto a creditor.
- Naked People Are Funny: A Running Gag involves Homer being accidentally stripped to the nude and shocking a passing dowager into fainting
- Noodle Incident:
Mr. Burns: Too busy keeping my sides from splitting. [In a matter-of-fact tone] It's happened before.
- When asked why he didn't help Homer in the infamous panda scene
- Mr. Costington isn't allowed on the third floor of his own store due to a "shoe sniffing problem" he has.
- Retirony: The Trope Namer. Mentioned when Chief Wiggum tells his financial planner that he's not going to create a retirement fund since he's a police officer, and, according to many cop shows and police movies, an officer who's only X amount of days from retirement (and tells his partner about what he's gonna do when he retires — usually, it'll be something like spending more time with his wife and kids) will always get murdered on the job. When the planner asks what he will do if he isn't shot, Sarah Wiggum burst into tears and Clancy is highly insulted.
- Screw the Money, I Have Rules!: While it at first seems like Homer is willing to do anything for money, he eventually gets sick of it and decides to donate his ill-gotten gains to charity.
- Skewed Priorities: When the kids notice that their family's car doesn't have back seats, Homer says he sold them to have money for fuel. The car then runs out of fuel and Homer says he spent that money on a novelty horn.
- Trap-Door Fail: When Smithers approaches Mr. Burns for a personal favor, Burns tries to drop him down his trapdoor, but Smithers had disabled it.
- Versus Title: Homer vs. Dignity.