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Willie is the groundskeeper at Springfield Elementary School and is a stereotypical angry Scottish man with a heavy Irish-Scottish accent. He was originally hired at Springfield Elementary as "swim teacher Willie." Unfortunately, after Skinner was trapped in the worm-filled pool for three days, he had the pool destroyed, and made Willie a groundskeeper. During weekends and vacations, he also tends the golfing greens, giving himself the appropriate name Greenskeeper Willie. He has claimed to originate from several different places in Scotland, and frequently gives contradictory accounts of his past life before arriving in Springfield. Willie once told a story of working at a mine that caved in, saying, "No one made it out alive, not even Willie!". It is implied that he immigrated to America illegally, as he had to take a citizenship test. Willie is incompetent and is quick to anger for little or no reason. He has shown great animosity towards both Principal Skinner and Bart Simpson, the latter of whom is often more than willing to make Willie the butt of his jokes. Willie once told Skinner that he had seen his own father hanged for stealing a pig. Groundskeeper Willie once discovered an Oil Well by accident because he was attempting to bury the school hamster. Because of the school's new wealth, he requested a crystal pail. However, after Mr. Burns stole the oil, which not only resulted in the loss of the school's newly gained fortune, but also causing the school to go into an even worse financial state than before due to the cost of dismantling the oil tower, Skinner was forced to lay off Groundskeeper Willie in order to preserve the remaining school budget, causing Willie to wish to murder Mr. Burns and "wound that Mr. Smithers." However, he ultimately wasn't able to get that chance when Mr. Burns was shot due to arthritis he gained from playing Space Invaders preventing him from even utilizing a gun. He once had a cache of "screw you money", but he ended up losing it all, presumably due to Artie Ziff cheating out ZiffCorp's shareholders.
Willie's hobbies include videotaping couples in cars, something which proves to the benefit of Homer Simpson when he is later wrongfully accused of sexual harassment. At one time, Willie was engaged to Sherry Bobbins until she recovered her eyesight—at which point, in Willie's words, "Suddenly the ugliest man in Glasgow wasn't good enough for her!" Willie was once given the job of teaching Bart Simpson. Lisa had taken a restraining order against Bart, so he couldn't legally go to the same school. Willie became Bart's teacher because, according to Principal Skinner, Willie's shack is the only place on school grounds "outside all laws of Man and God." His years of heavy work have given him amazing strength and a very muscular physique, which has been observed many times; for example, he rescues Bart from a marauding Alaskan timber wolf by wrestling it into submission. He also makes a prank on a play however Principal Skinner blamed his prank on Bart and expelled him but he welcomes him back as an apology when he talks to Skinner that he was behind the prank and Bart accepts the apology happily. Much like Ned Flanders, though, his physique is unremarkable when he is clothed, and seemingly morphs as soon as he is partially nude. Apparently, he has had sexual attractions to Sarah Ferguson, Duchess of York (more commonly known as "Fergie"), as he had mentioned while hallucinating as an after effect of Seth and Munchie's Peyote-laced juice (which was thanks to Homer) that he waited a long time for the moment where he could embrace Fergie passionately. Willie used to date a Swedish bikini model name Inga, but he told her she can't compete against his job because she'll never win.
 Treehouse of Horror
Willie has a tendency to get killed in the Treehouse of Horror episodes, getting killed three times in "Treehouse of Horror V", each time he attempts to be helpful or heroic, and each time he is felled by an axe in the back (he mutters, "Ach, I'm bad at this" after the third time). He is also killed in "Treehouse of Horror VI" by being burned to death, in "Treehouse of Horror XI" by a dolphin, in "Treehouse of Horror XVI" he is strafed and killed by Burns, in "Treehouse of Horror XVIII" by getting his head cut off by the tractor, and in "Treehouse of Horror XIX" by being eaten by the Grand Pumpkin although he is saved later. In "Treehouse of Horror XXII", though, he has the smallest part of all - he appears at the end as a cyborg cleaner, essentially a cyborg groundskeeper.
 The Simpsons Game
Willie appears as one of the contestants in the Duff Ultimate Eating Challenge in the level "Around the World in 80 Bites". He also appears in "Mob Rules" as one of the people Marge can use in her mob to protest the sales of the Grand Theft Scratchy video game to minors.
 Behind the Laughter
Groundskeeper Willie's first appearance was in the season two episode "Principal Charming". Originally, the character was just written as an angry janitor, and the fact that he was Scottish was added during a recording session. Dan Castellaneta was assigned to do the voice. Castellaneta didn't know what voice to use and Sam Simon, who was directing at the time, told Castellaneta to use an accent. He first tried using a Spanish voice, which Simon felt was too clichéd. He then tried a "big dumb Swede", which was also rejected. For his third try, he used the voice of an angry Scotsman, which was deemed appropriate enough and was used in the episode. Originally thought by the directors to be a one-shot appearance, Willie has since become a common recurring character. Matt Groening would later reveal that the character was based on Angus Crock, a kilt-wearing chef from the sketch comedy show Second City Television, who was portrayed by Dave Thomas.
A recurring joke, which was first shown in "Radio Bart", is that Willie appears to have a pot belly, but whenever he takes off his shirt, he is quite muscular. One of Willie's trademarks is a gruffly-spoken insulting retort, which take the writers a long time to come up with, although they do not consider them that funny.
 Cultural influence and legacy
Groundskeeper Willie's description of the French as "cheese-eating surrender monkeys" from the episode "'Round Springfield" has become widely used, particularly in the run-up to the war in Iraq. The New York Post used the phrase "Surrender Monkeys" as the headline for its December 7, 2006 front page, referring to the Iraq Study Group and its recommendation that U.S. soldiers be withdrawn from Iraq by early 2008. The line was "most likely" written by Ken Keeler.
The Times reported in late 2005 that "he is the most instantly recognisable Scot in the world: better known than Billy Connolly or Ewan McGregor, even Sean Connery." The same article quotes Simpsons creator Matt Groening as saying "We wanted to create a school janitor that was filled with rage, sort of our tribute to angry janitors all over the world".
In 2006, Groundskeeper Willie would be named the fourth best peripheral character in the history of the show by IGN, who said "high-points for the character were being trained to be civilized, wrestling a wolf that was let loose in the school and becoming a substitute for the French language teacher - 'Bon jourrr! You cheese-eating surrender monkeys!'" IGN would also name "My Fair Laddy", the only episode which centers around Willie, the best episode of the seventeenth season. Jim Slotek of Sun Media would call Willie the ninth best Simpsons supporting character, and also made a Top Ten quotes list, which included Willie's quote "Och, back to the loch wi' you, Nessie." from "Selma's Choice".
There have been some moments in the show where he has been known to imitate Montgomery Scott of Star Trek fame.