Short on funds, Homer approaches the ever-wealthy Mr. Burns for a token raise, but when Burns grants his request on the condition that Homer act as his personal jester, the Simpson family finds itself the subject of degrading and embarrassing activities.
When Bart gets his first A (he tried to "cheat" in order to get his mind off the fact that Edna Krabappel and Principal Skinner were making out in the classroom, not realizing that what he thought was cheating was actually studying), the family celebrates by eating at "The Singing Sirloin". Unable to pay the bill (due to Homer's credit card being rejected), they try to dine and dash, but are caught and end up having to play mariachi music to pay the restaurant back.
Marge sees that they're in financial trouble, and suggests they should see a financial planner. The planner tells them that their financial problems are due to Homer's being too stupid to follow a budget, and the only solution is more money—even declaring bankruptcy several times won't make them financially solvent.
Smithers takes some vacation time to star in a musical he wrote about Malibu Stacy. Mr. Burns takes the opportunity to go have some fun sans Smithers. Homer works up the courage to ask Burns for a raise, and he gets the chance when Burns wanders into the "cafe-torium." Homer asks for a raise, but Burns instead offers to give Homer money if he hits Lenny with a dish of pudding. Homer initially objects, but once he does it, Burns has a good laugh and hires Homer as his official "prank monkey."
Burns' pranks harm the dignity of both Homer and others, but Homer doesn't care as long as he gets paid. He also keeps his prank work a secret from his family, dodging the question when Marge asks where the extra money is coming from. Homer is unmasked, however, during a prank that involves Homer dressing as a new female panda donated to the Springfield City Zoo. The zoo's male panda takes a liking to Homer and makes him his mate. When Homer tries to escape, he gets caught on the fence and loses the head of his costume, and Lisa discovers him.
Lisa isn't proud that her dad is selling his dignity away, and tells him he needs to stand up to Mr. Burns. Homer succeeds in doing so, in spite of Burns' tempting him with more money. Homer is then left wondering what he can do with all the money he now realizes is ill-gotten gains, and Lisa suggests that he donate it to charity. Homer goes to Costington's and donates all the money to buy toys for poor children. The store owner is moved by this gesture and makes Homer the Santa Claus for the Thanksgiving Day parade. Homer's job in the parade is to wave from his float, yell "Ho, ho, ho! Merry Christmas!", and throw presents to the crowd.
Burns sees this as the perfect opportunity to pull a prank on the whole town. He pulls up beside Homer in another float (a pirate ship with the words "HAPPY PRANKSGIVING" on the side) and makes Homer an offer: one million dollars if he'll throw fish guts onto the crowd instead of presents. Homer is torn between the money and the fact that "Santa can't be evil!"
Moments later, Lisa sees "Santa" tossing fish guts at the crowd and is heartbroken, until she realizes that Homer is in the crowd with her. The Santa on the float is Burns: "Ho, ho, ho! Merry Fish-mas!" As seagulls invade the town, attacking all those with fish guts on them, Homer says that Lisa gave him an early Christmas present—the gift of dignity. They then get hit by fish guts.