12 Funniest Groundskeeper Willie Moments In Simpsons History

May 20, 2023

Homer, Marge, Bart, Lisa, and Maggie are the primary draw of "The Simpsons," but the series has no shortage of uproarious side characters. One of which is Groundskeeper Willie, the cantankerous janitor at Springfield Elementary School. His first appearance was in the Season 2 episode "Principal Charming," and he's since become one of the show's most beloved characters, due in no small part to his exaggerated Scottish accent and fiery temper. But Willie is more than just a stereotype; one of the funniest recurring gags is how his blue-collar getup hides his surprisingly ripped physique. And who could forget his colorful, if confusing, insults? (Five bucks to anyone who can tell me why "croquet-playin' mint-muncher" is a putdown.)

Over the years, Willie's influence has transcended "Simpsons" fandom. He is, after all, the reason why "cheese-eating surrender monkeys" has entered the modern lexicon. Mosey on over to the "Famous Glaswegians" section of the Glasgow City Council website, and there you'll find a certain ginger janitor among the company of important figures such as biochemist Lord Alexander R. Todd and poet Liz Lochhead. There are plenty of other ways that Willie has infiltrated the cultural landscape, but for now, let's take a look at his funniest moments in "Simpsons" history.

Bart brings his dog Santa's Little Helper to school, immediately attracting the attention of students and faculty alike. The pup gets into the air ducts, so Principal Skinner sends Groundskeeper Willie after him. Of course, never missing an opportunity to show off his signature Scottish six-pack abs, Willie rips his shirt off and has Lunchlady Doris grease him up to ... lubricate? ... his hunt for the adorable canine. Willie catches Santa's Little Helper, only to get stuck in a vent high above the school's basketball court, requiring the fire department to bring the pair down. This happens right when Superintendent Chalmers arrives for an unannounced visit, much to Skinner's terror.

During their 1990s heyday, the writers of "The Simpsons" knew how to stack jokes on top of jokes, and this scene is proof of their uncanny ability. Why Skinner thought it'd be a good idea for Willie to cover himself in cafeteria grease is anybody's guess, but his drill instructor-like order is hilarious, as well as Doris' willingness to apply the stuff to Willie's mostly naked body. Sci-fi fans will appreciate the "Alien" reference as Skinner, via a monitor too high-tech for Springfield Elementary, watches Santa's Little Helper corner Willie in a suspenseful scene, only to lick his greasy feet (gross). This scene's zenith, though, is when Willie falls from the vent, screaming, "Make way for Willie!" and lands on Chalmers, leaving an oily butt-shaped stain on his chest.

Just before he dies a gruesome death from Homer's negligence, Willie vows to get revenge by hunting Springfield's children in their dreams. He follows through on his promise, prompting Bart and Lisa to hatch a scheme to stop him. When their plan backfires, Maggie rescues them and seemingly defeats Willie in their shared dream. The Simpson kids wake up in the real world, wondering if Willie's still out there. Willie suddenly arrives off the bus; lacking his supernatural abilities, he relies on ineffectual childish gestures to spook them. He becomes even less scary when the bus takes off and he runs after it, claiming he left his gun on the seat.

This "Treehouse of Horror VI" segment is called "Nightmare on Evergreen Terrace," wherein Groundskeeper Willie plays a sendup of Freddy Krueger. It's a creative turn for the character whose horticultural tool — a rake — makes for an amusing analog to Krueger's signature bladed glove. But for all the dread this nightmarish version of Willie creates, his final human form is the perfect counterpoint. Gone are his sadistic quips and otherworldly powers, as he's nothing more than a cranky, rambling janitor who thinks yelling "Boo!" is enough to instill fear in his prey. Willie even tells the kids, "Wait here, please," as he chases the bus, making him about as threatening as a teddy bear.

"Treehouse of Horror V" sees Groundskeeper Willie appearing in all three segments, only to get killed in each of them in the exact same way. In "The Shinning," Willie plays a parody of "The Shining" character Dick Hallorann. Bart mentally reaches out to Willie when Homer goes mad and tries to kill the family, but Willie meets his end with an ax to the back. He shows up again in "Time and Punishment" to rescue Homer but gets axed by an alternate-reality version of Maggie. His death is no different when he arrives to save Bart, Lisa, and Milhouse in "Nightmare Cafeteria."

Okay, technically these are three separate moments, but together they form such a funny recurring gag that I think it's fine to count them as one. The great irony is that Willie, typically selfish and meanspirited, is trying to be the hero in every story, only to suffer a gruesome fate. The nonchalant manner of his death is what really makes it so classic; when Homer kills Willie in the hotel, Marge gasps at his bloody corpse on the floor and says, "Oh my! I hope that rug was Scotchgarded." The third time Willie meets his maker, he utters, "Ugh, I'm bad at this." Don't worry, Willie — you'll always be my knight in shining denim.

When Bart develops a crush on Jessica, Reverend Lovejoy's daughter, he tries to woo her by stifling his troublemaking tendencies and cultivating a "nice guy" image. However, Jessica's unimpressed with the act, much to Bart's frustration. To satisfy his urge to raise hell, Bart spots Groundskeeper Willie giving a talk about traditional Scottish wear in an event called "Scotchtoberfest." Bart ties some balloons to Willie's kilt, which lifts it and reveals his little Willie to an unsuspecting audience. However, this is revealed to be an elaborate sting operation set up by Principal Skinner, resulting in Bart receiving three months of detention. But he wasn't the only one fooled by Skinner, as Willie didn't know that "Scotchtoberfest" wasn't real.

Despite Willie's Scottish accent and love for his country, he seems to know nothing about Scotland whatsoever. In his lecture, he states that "the kilt was only for day-to-day wear. In battle, we donned a full-length ball gown covered in sequins. The idea was to blind your opponent with luxury." Watching "Braveheart" would give someone a better understanding of Scottish history than listening to Willie. He couldn't even spot a phony holiday that celebrated his own culture, for goodness' sake. Did he really think there was a whole event dedicated to Scotch whisky? As a fan of the Glenlivet myself, I don't blame Willie for being so angry at Skinner for being used like that.

Bart hasn't studied for an upcoming test, so he's been faking sick to get out of taking it, with each excuse becoming more outrageous than the last. Mrs. Krabappel starts to catch on, and even Grandpa Simpson — who's been picking up Bart from school since Marge got a job at the nuclear power plant — reminds him of "The Boy Who Cried Wolf." Finally, Mrs. Krabappel puts an end to Bart's charade and makes him take his test outside in the hallway. Unfortunately, a wolf has escaped from a taping of "The Krusty the Clown Show" and attacks Bart. Good thing Groundskeeper Willie's on hand to battle the vicious animal.

Willie may seem like a humble janitor, but one of his funniest aspects is how many skills he has in his arsenal — like wolf wrestling, for instance. What's funnier is that he utters a cool one-liner ("Hey, wolfie! Put down that hors d'oeuvre — it's time for the main course!") before ripping off his shirt to reveal his chiseled form in a move that would impress Arnold Schwarzenegger. During his brutal bout with the wolf, Willie casually tells Bart to go back to class, making him all the more badass. He bests the beast in combat, but at least he's a gracious winner; Willie gives the beleaguered wolf some hooch as a consolation prize, while reminding it that he's been fighting wolves since he was young.

"Lard of the Dance" features Homer and Bart embarking on yet another hair-brained scheme, this time selling used grease for money. After several failed attempts to turn it into a business, Bart recommends giving their plan one more shot by stealing grease from the Springfield Elementary School cafeteria. The pair sneak into the school and begin sucking the grease deposit through a hose, only for Groundskeeper Willie to walk in on them. Homer momentarily distracts Willie by telling him they're foreign exchange students from Scotland. But when Willie notices them stealing his "retirement grease," he gets into a brutal fight with Homer, strangling the elder Simpson with his own hose.

The ginger janitor once again displays his hilarious ignorance of Scottish culture in this scene; when Homer lies about being from the made-up region of "North Kilttown," Willie responds with, "No foolin'! I'm from North Kilttown!" Either that or Homer just has an unusually in-depth knowledge of Scotland. And how does Willie keep getting into greasy chases in the school's air ducts? He easily beats Homer into submission, proving he's the wrong man to anger, especially when his "retirement grease" is at stake. This does beg the question: Is Springfield Elementary School so impoverished that its only benefit to staff is a large supply of used oil? Considering Willie lives in a shack on the school's grounds, it's as good as a 401(k).

Stressed from catering to her chaotic family's every need, Marge decides to bring on a nanny to help around the house. And that's when Shary Bobbins enters their lives. Perfect in almost every way, Shary looks after Bart, Lisa, and Maggie, and helps restore order in the Simpson home. One day, while taking the kids for a walk in the park, Shary bumps into Groundskeeper Willie, who's performing a one-man-band version of Michael Sembello's 1983 hit, "Maniac." Willie recounts how he and Shary were about to get married until her vision was restored and, upon seeing how ugly he was, ended their engagement.

While it's sad that the only woman Willie could attract is a blind one, I highly doubt that it was just his scruffy looks that Shary objected to. She even tries to extend an olive branch by telling him how nice it is to see him again, to which he angrily replies, "That's not what you said the first time you saw me!" before stomping away. This episode's writers deserve extra points for combining Willie's parody of Dick Van Dyke's "Mary Poppins" character, Bert, with Jennifer Beals' "Flashdance" character, Alex, and somehow making it work. It's a bizarre form of lateral thinking that made this era of "The Simpsons" so beloved.

In "The Canine Mutiny," Bart mistakenly gives away Santa's Little Helper to a collection agency after making a series of expensive charges to a bogus credit card. Bart realizes his error and sets out to find his old furry friend. A repo man tells him that he sold Santa's Little Helper to some guy in a dress. Bart thinks it's his aunt Patty, only to learn that the dog's buyer was really Groundskeeper Willie. When Bart visits him, Willie says that he "ate" Santa's Little Helper, including his little face and his guts, much to Bart's horror. However, he quickly realizes that Willie was actually saying he "hated" Santa's Little Helper, and that he gave him to the church.

"The Simpsons"' writers have wrung considerable humor out of Willie's heavy accent over the years, but this was one of the best gags, as they took full advantage of the Scottish tendency to not pronounce the American "h" sound. When a relieved Bart is leaving Willie's home, he says that he also "ate the mess 'e made on me rug;" Bart initially thinks that Willie again meant "hate" instead of "ate," but Willie confirms the gross truth when he follows up with "ya heard me!" Come on, Willie, couldn't you have gotten Lunchlady Doris to whip you up something with your retirement grease? Then again, we can't expect someone who lives in a shack on school property to have a discriminating palate.

Mr. Burns has been shot, and everyone in Springfield is a suspect. Chief Wiggum leads the investigation and interrogates anybody who may have a reason to get revenge on Mr. Burns, starting with those who were negatively impacted by his tapping of the oil well underneath Springfield Elementary School. Groundskeeper Willie is brought in for questioning, but only annoys the officers; he keeps crossing and uncrossing his legs, and because he's wearing nothing under his kilt, the police officers are given a sight they'd rather not see. Willie maintains that he couldn't have shot Mr. Burns due to arthritis he got from "Space Invaders" in 1977, though not the video game.

Leave it to "The Simpsons" to take one of the sexiest moments ever – Sharon Stone's infamous interrogation scene from "Basic Instinct" – and turn it into one of the unsexiest moments ever. Willie's unintentional flashing anger the police officers so much that one of them even points a gun at him and says, "This is your last warning about that," implying that Willie had been giving them an eyeful throughout the questioning. It's a hilariously gross-out moment from Willie, but then again, what did you expect from the guy who takes every opportunity to needlessly rip his shirt off? Is Scotland much more lax about public nudity, or does Willie just have a thing about showing off his body?

Bart forges a letter from his mom to excuse him from school for the day. Mrs. Krabappel suspects he's lying, and takes the note to Principal Skinner, who concludes that Bart is playing hooky. Determined to find out where Bart is, Skinner teams up with Groundskeeper Willie to interrogate Lisa. Willie demands Lisa tell them what she knows about Bart's whereabouts, while Skinner warns her about angering Willie. However, Lisa merely chuckles at their failed good cop-bad cop routine, pointing out that Skinner started off as the bad cop and Willie as the good cop, and they got mixed up and reversed roles 10 minutes earlier. Lisa cracks up even more when they switch roles again without realizing it.

Willie and Skinner are a priceless duo here as they attempt to recreate a tactic they know only works on TV. This scene kicks off with Willie in the "bad cop" role, which better complements his grumpy personality. But the scene turns from funny to downright side-splitting when Skinner takes on the "bad cop" role ordering Lisa to give up what she knows, to which Willie responds with a nervous "Ya better tell him, Lassie — I cannae control him when he gets like this!" It's always a blast seeing Willie and Skinner join forces to solve a problem at the school; whether it's catching a dog or questioning a little girl, they make perfect foils for one another.

The Movementarians is a new-age cult that's swept through Springfield, converting everyone in town to its bogus set of beliefs. Well, not quite everyone; Marge, Reverend Lovejoy, Ned Flanders, and Groundskeeper Willie are the only ones who haven't fallen prey to the weird dogma of "the Leader." Together, they kidnap Homer, Bart, Lisa, and Maggie as part of their plan to undo the Movementarians' influence. While Marge makes headway with the kids, Willie has a serious sit-down with Homer, demanding to know what makes "the Leader" so great. However, when Homer says that the Leader knows all and sees all, Willie immediately falls in love with the cult.

When Willie is revealed to be one of the few Springfieldians to not be seduced by the Movementarians, it seems that it's his stubbornness that saves him, making his quick indoctrination all the more surprising. It didn't even take much to brainwash him into believing the cult's silly lore; when Homer tells Willie that the Leader plans to someday transport everyone to a wonderful new planet, he responds with, "Oh, this leader — he sounds like a grand fella!" However, the icing on the cake is when Marge tries to interrupt Willie's "deprogramming" session, only for him to snap at her for preventing him from learning more about his Leader. Oh, Groundskeeper Willie ... if everyone else in town jumped off a bridge, would you do it? Wait, don't answer that.

"Marge Simpson in: 'Screaming Yellow Honkers'" opens with a faculty talent show at Springfield Elementary School, with the teachers and staff members engaging in one cringey act after another. Groundskeeper Willie's bit does some weird observational comedy comparing the ways that North and South Edinburgh golfers putt. To Willie's surprise, the American audience doesn't understand his highly localized wisecracks, so he tries to win them over with an enthusiastic toot from his bagpipe. When that fails, he goes on an angry rant about how he's only entertaining when he's cleaning up a mess from their kids. This, of course, is when the audience breaks into laughter.

Outside of the aforementioned gaudy insults he hurls at pretty much everyone, Willie's not exactly known for his sense of humor. But for some reason, someone thought he'd be a great addition to the show's lineup, delivering jokes about everyday life. However, I'd like to think that he volunteered for the performance and that he's been sitting on what he thought was dynamite material that was finally ready to be tested in front of a live audience. Sure he bombed, but that was his first time, and he at least managed to recover himself at the end. Believe it or not, I've actually seen far worse open-mic comics since moving to Los Angeles. Don't let 'em see you sweat, Willie.