After Santa’s Little Helper gets into the air vents at the school, Willie goes in to catch the pup — after ripping off his clothes and getting greased up by Lunchlady Doris.
This sequence is stacked with jokes, from the “Alien” references to the Scotsman falling from the vents, screaming, “Make way for Willie!” and landing on Superintendent Chalmers.
Willie makes an appearance in a “Treehouse of Horror VI” segment called “Nightmare on Evergreen Terrace,” where he becomes a Freddy Krueger-like villain.
Once the children wake up from their shared dream, all that remains is the regular human Willie, a cranky, rambling janitor who resorts to childish gestures to try and spook them.
The groundskeeper makes another appearance in a “Treehouse of Horror” segment that parodies “The Shining,” where he has an unfortunate role similar to Dick Hallorann.
While he meets his fate with an ax to the back in the parody, Willie actually appears in all three segments of the special, and each time he ends up getting axed.
Bart tries to impress Reverend Lovejoy’s daughter with his pranks and ties some balloons to Willie’s kilt during an event called “Scotchtoberfest,” causing him to flash the crowd.
Before the prank, Willie gives an astonishingly inaccurate lecture: “The kilt was only for day-to-day wear. In battle, we donned a full-length ball gown covered in sequins.”
After Bart is forced to take a test out in the hallway, a wolf that escaped from a taping of “The Krusty the Clown Show” attacks Bart — luckily, Groundskeeper Willie is there.
Wille says, “Hey, wolfie! Put down that hors d’oeuvre — it’s time for the main course!” and proceeds to rip off his shirt and wrestle the wolf, beating the animal into submission.