32 seasons, 706 episodes. So much content from The Simpsons since airing its first season in 1989, so many characters, so many episodes. One thing the series has always been particularly good at is parodying both real-world figures and pop culture characters, doing so in as little time as one episode. The Simpsons has given us countless great one-off characters, and allow us to celebrate some of those here.
Episode: Homer vs. the Eighteenth Amendment (Season 8, Episode 18)
The Simpsons‘ on-brand take on telling the story of prohibition, Homer vs. the Eighteenth Amendment, is one of the many “all-time great” episodes from the show and is one of the smartest usages of one-off characters to tell a story.
Featured in it is Rex Banner, who is just so much fun. Based on Robert Stack’s portrayal of famous prohibition agent Elliot Ness in The Untouchables series, Banner is so clever and entertaining, you actually want to see more of him. Highlights include him arresting Ned Flanders on suspicion of being drunk solely because of how Ned talks, and several failed attempts to arrest people for breaking prohibition.
Rex Banner: Pet shop, eh? Well, I have one thing to say about that. What kind of pet shop is filled with rambunctious yahoos and hot jazz music at 1:00 in the morning?
Moe: Er, uh… the… best damn pet shop in town!
Episode: New Kids on the Blecch (Season 12, Episode 14)
All that’s needed to justify his appearance in this list is the following exchange:
L.T. Smash: It’s a three-pronged attack: sub-liminal, liminal and super-liminal.
L.T. Smash: I’ll show you. (leans out of window) Hey, you! Join the Navy!
Episode: Marge vs. the Monorail (Season 4, Episode 12)
One of Phil Hartman’s many great roles across the series, Lyle Lanley is the villain of the story in Marge vs the Monorail. It’s funny to think when the episode initially aired, it was not received by critics or by the cast and crew. But in time it became a classic – much due to Phil Hartman’s Lyle Lanley.
Lyle Lanley is great. An experienced charlatan who has no qualms in being just so stupidly evil. He has the famous “Monorail” song, a charismatic voice, a thoroughly enjoyable zealousness – he’s perfect. He set the tone for future one-off characters and also the tone of the show for the many years to come. Hell, even just as cartoon villains go, he’s one of the best ever.
Episode: Lisa’s Substitute (Season 2, Episode 17)
While many of the one-episode characters are very much comedic effect or don’t really have much impact in the development of The Simpsons family, Mr. Bergstrom provides one of the most heartfelt episodes in the entire show’s run during Lisa’s Substitute.
“You are Lisa Simpson”.
Voiced brilliantly by Dustin Hoffman (under the pseudonym Sam Etic, or ‘sem-etic’), he is the first person in Lisa’s life who she feels understands her, and challenges her to be the best version of herself. When he departs and leaves Lisa in a feeling of ruin, it leads perfectly into one of my all-time favourite Simpsons endings – as Homer comforts his children about their bad days and offers some all-time life advice. I get emotional every time I rewatch this episode.
Episode: You Only Move Twice (Season 8, Episode 2)
You Only Move Twice is possibly my favourite Simpsons episode for a number of reasons. It’s funny, it’s got great pacing, it’s got wonderful character stuff, and it is one of the best “Homer gets a new job” episodes.
Hank Scorpio hires Homer to work for him and overlook his nuclear division in his somewhat sinister workplace. Scorpio is, of course, one of the all-time tributes to the James Bond movies. It does one of my personal favourite things in literature: detailing the benign daily life of a supervillain’s henchman.
Scorpio is just iconic. I don’t think there’ll ever be another one-off character as good as him.