Groundskeeper Willie
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Willie is voiced by Dan Castellaneta. He is the school's groundskeeper, with flaming red hair and an outrageously exaggerated Scottish accent. His years of heavy work have given him an amazingly muscled physique, occasionally revealed, notably when he had to crawl through ventilation shafts to retrieve Santa's Little Helper. Needing some assistance to get through the narrow tunnels, he turns to Lunchlady Doris to coat him with oil, with the memorable lines, "Lunchlady Doris, Have you got any grease?" She replies by saying, "Yes. Yes we do." Willie bellows "Then grease me up, woman!" as he dramatically tears his shirt open, to which she replies, "Okey-dokey."
Sometimes, Willie wears a kilt. He does not however wear anything under the kilt - the mark of a true Scotsman. At Scotchtoberfest, Bart attaches a number of balloons to Willie's kilt. This led to the kilt flying up. The gathered crowd gasped, and one woman fainted. In response, Willie cried, "Ach! 'Tis no more than what God gave me, you puritan pukes!"
In the second part of "Who Shot Mr. Burns?", Willie has his kilt on while being interviewed by the police. During the interview Willie uncrosses and then recrosses his legs. In response, the officers point a gun at Willie with a warning to stop doing that. The scene was a spoof of Sharon Stone's interrogation scene from the film Basic Instinct.
In the episode "Monty Can't Buy Me Love", Willie is re-united with his mother and father on the banks of Loch Ness, Scotland, where Mr. Burns leads a successful expedition to catch the Loch Ness Monster - Nessie - and bring it to Springfield.
According to Superintendent Chalmers, Willie is an escaped patient from a mental hospital that Skinner hired. According to Willie, he has worked at the school for 20 years, just as long as Principal Skinner, so he was likely hired soon after Skinner got his job.
At one time, Willie was engaged to Sherry Bobbins (a parody of Mary Poppins), until she recovered her eyesight at which point, in Willie's words, "suddenly the ugliest man in Glasgow wasn't good enough for her anymore."
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. He says America thinks it's wrong but every Scotsman does it. Compare: Hagrid from the Harry Potter books and films.
Willie's nationality is also hinted to be the cause of his hostility. Example:
Willie: "Brothers and sisters are natural born enemies! Like Englishmen and Scots! And Welshmen and Scots! And Japanese and Scots! And Scots and other Scots! Lousy Scots! They ruin Scotland..."
Skinner: "You Scots sure are a contentious people."
Willie: "You just made an enemy for life!"
It was recently revealed that Willie's personal enemy is another Groundskeeper that speaks with a heavy Irish accent: Seamus.
When Homer pretended to be a Scot and said to Willie that he was from "North Kilt-Town," Willie responded: "Noo fooling, I'm from North Kilt town too! You know Angus Mcleod?"