Depending on who you talk to, The Simpsons is either past its prime, with a worryingly wonky ratio of good episodes to bad since around season nine, or still pretty good – people just love to bleat on about how things were ‘better in my day‘. One thing that’s remained consistent throughout its 26 seasons so far, at least, is the show’s ability to pull from a huge, ever-expanding cavalry of supporting characters – some of whom only need one episode to make their mark on the show’s legacy. So, from Bond villain-cum-model employer Hank Scorpio to the lawsuit-proof Sherry Bobbins – who remember, has no affiliation whatsoever to the film Mary Poppins, and is an original creation, like Rickey Rouse and Monald Muck – here’s 10 Springfieldians who only appeared only once, but still wrote their way into The Simpsons’ history.
10 Rex Banner
Appears in Season Eight, Episode 15 – Homer vs The Eighteenth Amendment – The surest indicator of an episode’s strength is it’s sheer quotability, and Springfield’s unfortunate introduction to prohibition brings out the best in its core cast, as well as one-time character Rex Banner, who enforces the new ban on alcohol while spitting out dated slang and showing total disdain for a banana kaboom.
9 Vicki Valentine
Appears: Season Eleven, Episode Twenty – Last Tap Dance In Springfield – Later episodes of The Simpsons might not have been as engaging, but former child star turned terrifying tap tutor Lil Vicki is a fierce, egotistical performer whose instant dislike of Lisa and her average tap potential make for the episodes best moments. By tapping out morse code messages during the war (until her shoes filled with blood) and administering painful dimple-inducting injections to her students, the psychotic teacher has a touch of 30 Rock’s Jenna Maroney about her – in the worst way possible.
8 Mr Bergstrom
Appears: Season Two, Episode Nineteen – Lisa’s Substitute – Season Two saw The Simpsons bolster the show’s belly laughs with character beats that were emotionally powerful. Take this poignant, Lisa-centric episode, for instance. When Lisa connects with her substitute teacher (voiced by Dustin Hoffman, who worked under a pseudonym due to contractual issues) it’s not hard to understand why she becomes so distraught when he has to eventually on move on.
7 Shary Bobbins
Appears in: Season Eight, Episode Thirteen – Simpsoncalifragilisticexpiala-D’oh!-cious – Though Julie Andrews was approached to voice the vulgar rip-off of her Mary Poppins character, she had to turn it down due to Broadway commitments. Without her, though, Shary Bobbins is still one of The Simpsons’ smartest, funniest and somehow also bleakest one-off characters – her optimism and cheer sucked out of her by the vacuum of chaos that is The Simpson family.
6 Jessica Lovejoy
Appears: Season Six, Episode Seven – Bart’s Girlfriend – Bart Simpson’s infatuation with an emotionally repressed evil genius (who happens to be Reverend Lovejoy’s daughter) is made even better by the fact she is voiced by Meryl Streep. Jessica Lovejoy has made cameo appearances since her debut (she’s even in the new intro) but in her only speaking role she’s the perfect foil for Bart – relentlessly cruel and completely devoid of any moral compass.
5 Hank Scorpio
Appears: Season Eight, Episode Two – You Only Move Twice – The Simpsons mocked Bond idioms superbly by having their own take on a megalomaniac super-villain. Only Homer could find himself with a boss like Hank Scorpio – a charming and successful employer with an in-depth knowledge of hot spots to buy a new hammock, who, when not busy picking sugar from his trouser pockets, bullies the UN and is on a one-man mission to conquer the East Coast of America.
Voiced by: Harvey Fierstein
Appears in: Season Two, Episode Two – Simpson and Delilah
Karl is an enigmatic man hired as Homer’s assistant when he gets a promotion at work; a guardian angel who steers Homer to do the right thing while he’s suffering a serious (and perhaps accurate) case of imposter syndrome. For all his smooth talking, it’s the things Karl doesn’t say that make him interesting, as the audience learns barely anything about him.
3 Leon Kompowsky (“Michael Jackson”)
Appears in: Season Three, Episode One – Stark Raving Dad – Though he was not allowed to sing – that was done by singer Kipp Lennon – Michael Jackson was allowed to record under a pseudonym just like Dustin Hoffman the year before when he made this S3 cameo. Jackson played a bricklayer who was in a psych ward for thinking he was Michael Jackson, a testament to the show’s unwavering commitment to bizarre but touching storylines. Following the episode’s success, Prince was asked to voice Leon Kompowsky in a second appearance, which was written but never went into production.
2 Lyle Lanley
Voiced by: Phil Hartman
Appears: Season Four, Episode Twelve – Marge vs The Monorail
There’s a reason Marge vs The Monorail is one of the most popular episodes of the Simpsons: it’s brilliantly silly. There’s the ridiculous storyline (Lanley cons the townspeople to invest Springfield’s money into a dodgy monorail that is riddled with faulty mechanics), the giddy monorail song (“The ring came off my pudding can!” “Take my penknife, my good man”) but the best part is Lanley himself.
1 Frank Grimes
Appears: Season Eight, Homer’s Enemy – And so we arrive at number one. Honourable shout-outs to Johnny Cash’s Space Coyote, to Poochie and Roy, to Linguo and so many other one-episode Simpsons favourites. But Frank Grimes, in the space of one hilarious and heart-breaking 22 minutes, got to the very heart of Homer’s buffoonery, and our weird attraction to it as an audience.