"Homer vs. Dignity" is the fifth episode of season 12 and aired on November 26, 2000. The episode was written by Rob LaZebnik and directed by Neil Affleck. Leeza Gibbons guest stars as herself.
Short on funds, Homer approaches the ever-wealthy Mr. Burns for a raise. But when Burns grants his request on the condition that Homer act as his personal jester, Homer finds himself in a series of degrading and embarrassing situations.
Bart gets an A+ on an Astronomy quiz, and the Simpson family celebrate by having dinner at The Singing Sirloin, where the singing waitstaff sing "Happy First A" for him (to the tune of "Happy Birthday"). Bart tells the story of how he got the A: He was alone in the classroom when Principal Skinner and Mrs. Krabappel burst into the room, having a make-out session. Bart hid in the closet and intently concentrated on a chart of the Solar System to distract himself from the sounds they were making. Later, when he took the test, he found that the answers were stuck in his brain. Back in the present, finishing his story, Bart describes it as "like a whole different kind of cheating".
The family rejoice in Bart's achievement, but when it comes time to pay for their dinner, they are unable to pay the bill due to Homer's credit card being rejected. The family try to dine and dash, but are caught and end up having to play Mariachi music to pay their dinner bill.
When they run out of gas on the way home, Marge sees that they're in financial trouble, and suggests they should see a financial planner. They visit Let's Get Fiscal, where Lindsey Naegle 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. When Naegle asks for her fee, Marge and Homer do a repeat of their dashing attempt at The Singing Sirloin, but this time they succeed.
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 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 store's big 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.
Thanksgiving Day turns out to be a beautiful day for a parade, as commented on by co-hosts Kent Brockman and Leeza Gibbons during the parade's TV coverage. Homer is well-received as Santa Claus, even though he mixes up his line and yells "Merry everyone!" Burns, however, sees the parade 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 the family. The Santa on the float is Burns, who yells "Ho, ho, ho! Merry Fish-mas!" as he tosses fish guts at the crowd. Seagulls then invade the town, attacking all those with fish guts on them. As townspeople flee in panic, Marge asks what's going on, and Homer says that Lisa gave him an early Christmas present—the gift of dignity.