A Simpson-ized parody of My Fair Lady sees Lisa training the brash Groundskeeper Willie into being a proper gentleman; Homer sells his body as a human billboard to save his trademark blue pants from being discontinued.
- A Day in the Limelight: For Willie.
- Beyond the Impossible: During his time as the school's new groundskeeper, Mr. Largo somehow drove the tractor to the roof. Even he doesn't know how he did it.
- Fan Disservice: The Super Bowl ad for blue pants features a tubby guy shaking his fat to the tune of "Little Elephant Walk". For some reason, the camera closes up on his wobbling rear.
- "I Want" Song: Parodied. When Lisa asks him if he wants a better lot in life, Willie sings, "All I want is a place somewhere." Then everything stops, as that was all he wanted. Bart suggests aiming higher, leading into a longer song ("Wouldn't It Be Adequate?"), where Willie would like such things as his shack repaired, matching shoes, and underwear for when he's wearing a kilt.
- Overly Long Gag: The Fan Disservice ad for Blue Jeans in which a fat man dances is this In-Universe and out. The audience gets about twenty seconds of the man dancing before Homer asks the Blue Pants executive how long is the ad. The executive then says he doesn't know the exact length, but it's so long that he's never been able to make it to the end himself.
- Plagiarism in Fiction: While shoving Krusty's face to a dessert, Willie makes a joke that Krusty likes so much he asks for permission to use it at his show. Krusty says he'll use the joke with or without the permission.
- Pygmalion Plot: As the title suggests.
- Rags to Riches: Willie looks the part and is very much praised for his new attitude, but soon, the snobs of the higher class start to annoy him to the point where he eventually reverts back to his former self, not without thanking Lisa for thanking her time with him.
- The Red Stapler: In-universe. A disastrous Super Bowl ad drives blue pants to the verge of extinction. Then, after Homer uses his head as a billboard, and everybody begins using blue pants.
- Jimbo and Kearney make a bet about traveling the world on eighty days.
- At the science fair, Willie is introduced as "G.K. Willington", a reference to writer G.K. Chesterton.
- Worldwide Pants is named after David Letterman's production company.
- Thing-O-Meter: One of the projects presented at the science fair is a surprise-o-meter.
- Whole Plot Reference: To My Fair Lady.