As fans of The Simpsons will know, the town of Springfield is full of hilarious, wacky, eccentric regulars. From the nefarious Charles Montgomery Burns to the Simpson family itself, these iconic characters really make the show what it is. Sadly, viewers have had to say a fond farewell to some of them as the years have gone by, but the core cast are some of the most recognizable and memorable in TV history.
Everybody will have their favorite Springfieldians and their favorite episodes, but true Simpsons fans appreciate the one-time characters just as much. The best of these made indelible impressions on viewers’ hearts, despite appearing in just one episode.
10 Hank Scorpio
Hank Scorpio is probably the most amiable supervillain in media history. He’s a walking parody of James Bond’s most devious enemies, but he’s as superficially charming and kind a man as has ever graced the show.
Appearing in Season 8 highlight “You Only Move Twice,” Scorpio is the head of the Globex Corporation. He is Homer’s boss for a brief period during the family’s short-lived move to Cypress Creek. He’d have been a wonderful boss and role model, if not for his unfortunate tendency towards trying to take over the world. A classic character fans would love to see more of (while he’s shown in “The Simpsons Guy,” that’s a Family Guy episode, and his briefest of showings in “500 Keys” doesn’t really qualify either).
9 Hugh Parkfield
On the surface, Hugh Parkfield is far from the most loveable and significant of The Simpsons characters. After all, he’s judgmental and haughty, appearing only in a brief flash-forward to Lisa’s future. Nonetheless, he’s very notable for various reasons.
In the episode “Lisa’s Wedding,” a fortune teller shows Lisa a glimpse of her future, as her 23-year-old self meets, falls in love with and almost marries British college student Hugh Parkfield. He seems kindly and loving, but shortly before the ceremony, he reveals that he thinks Lisa’s family are beneath them both. Though he left a sour taste in the mouth, Parkfield is a memorable character who starred in an episode that was set in the future and told well. Episodes tend to struggle where past and future settings are utilized, but “Lisa’s Wedding” is another highlight for its honest portrayal of relationship woes.
8 Molloy
It’s quite common for brand-new characters to be created simply as a plot device. Naturally, these plots usually revolve around a silly new scheme or one-episode career change of Homer’s. In the case of “Homer The Vigilante” (Season 5), a cat burglar was called for. That cat burglar would be Molloy.
A softly spoken (voiced by Sam Neill, no less) and charming resident of the Retirement Castle, Molloy is eventually captured. He outwits the townsfolk once more, though, tricking them into believing he has buried treasure somewhere in town and escaping jail while everybody searches for it. A compelling ‘villain’ with a big heart, Molloy has appeared elsewhere in series media (including The Simpsons Movie) but deserves to return to the show too. Perhaps another reference in another The Simpsons movie, is one’s ever produced.
7 Floyd
Floyd is a more obscure Springfield resident that even hardened fans may have entirely forgotten. This creation of Professor Frink’s appears not only in just one episode, but in one very specific scene.
In “Treehouse of Horror VIII,” The Fly Vs. Fly segment sees the Simpsons at the eccentric professor’s yard sale. They purchase a Matter Transporter that leads to this tale’s disastrous events, but before that, Floyd is seen. The cunning robot attaches a ‘sold’ sign to itself and nonchalantly tries to escape, but Frink notices and reprimands, “Nice try, Floyd, but you were designed for scrubbing and scrubbing is what you shall do!” Insignificant as it may be, this moment hints at the intelligence of Frink’s funniest, most frighteningly self-aware creation.
6 The Happiest Man In Springfield
It’s true that some episodes of the show have aged very badly. Some attitudes and depictions just wouldn’t fly today, and “Hurricane Neddy” (Season 8) isn’t delicate with the subject of Ned Flanders’ mental health.
When Flanders’ home is destroyed by a hurricane, the townsfolk rebuild it, and (before seeing how poor their work was) Ned declares himself the happiest man in Springfield. In an excellent example of just how far the show will sometimes go for a joke, the camera pans to a jovial man who is the actual ‘Happiest Man In Springfield,’ who exclaims, “No, no! Not me, friends! He’s talking about himself. But thanks for looking!” This is the only time this man has made an appearance to date, which is part of the joke, but who is he? What’s he so happy about? A brilliant blink-and-you’ll-miss-it cameo with a lot of potential.
5 Lyle Lanley
Even those dedicated fans rewatching the show may have forgotten all about ‘The Happiest Man In Springfield’ and other such additions. However, this one-episode wonder is unforgettable.
Lyle Lanley is the dastardly charmer who tricked the people of Springfield into building a cheap, dangerous and profitable-for-Lanley monorail. In Season 4’s “Marge vs. The Monorail,” he deceives the town, reveals the extent od his scheming history and receives his vicious comeuppance, all in the space of a single episode.
4 Robert Terwilliger Sr.
Even those who have only dabbled in The Simpsons will be familiar with Sideshow Bob. The eloquent and villainous Bob is voiced by Kelsey Grammar. Grammar’s vocal talent and rich baritone are put to great use in the show, as is his legacy as Dr. Frasier Crane (in Cheers and Frasier).
In “Brother From Another Series,” Sideshow Cecil made his first of few appearances, played by David Hyde Pierce (Frasier’s brother Dr. Niles Crane). The true masterstroke, however, was the one and only appearance in the show from Robert Terwilliger Sr., father of Bob and Cecil (“Funeral For A Fiend”). He was voiced by none other the late John Mahoney, or Martin Crane in Frasier. The Terwilliger patriarch proves just as devious and deadly as his sons, with his own scheme to dispatch Bart Simpson by faking Bob’s death. He steals the show during his screen time.
3 Beatrice Simmons
Beatrice Simmons is another highly underrated character that many fans of the show may have forgotten about. In fact, following her one starring role in the episode “Old Money,” her tombstone is seen later in the series, marked “Beatrice Simmons (Grandpa’s Girlfriend).” That speaks volumes about her perceived importance by some.
Regardless, this underappreciated character has a hugely important role in Abe Simpson’s life. This Series 2 episode presents Beatrice’s short-lived love affair with Grandpa Simpson, as the pair’s blossoming romance is cut tragically short by Beatrice’s death. In her gentle, kindly way, she inspired Abe to embrace his feelings, forgive his son (after one of their many arguments) and gradually become less of a curmudgeon. Had Beatrice remained, her relationship with Abe could have been great for his character.
2 Frank Grimes
Technically, the long suffering Frank Grimes made an in-the-flesh cameo in “I, Carumbus” (Season 32), as well as outside-of-canon roles in Treehouse of Horror XII and XXVII. This was not the ‘original’ Grimes fans know and love, however. This sorry soul was introduced and met his grim end over the course of one episode: the legendary “Homer’s Enemy.”
One of very few characters ever to question the status quo, Grimes saw Homer’s complete incompetence at the power plant for what it was. His futile battle to expose the danger Homer posed was both hilarious and tragic to watch, and he remains one of the show’s most-loved cameo characters.
1 James Woods
The Simpsons has had a tumultuous history with video game adaptations (will there ever be a sequel to the fantastic The Simpsons: Hit And Run?), and its many, many celebrity cameos have been quite hit and miss over the years too.
James Woods, however, absolutely nailed his one-off role on the show. He appeared as himself in Season Five’s “Homer And Apu” (as well as “The Simpsons Guy”), serving as a Kwik-E-Mart clerk to prepare himself for a role as a retail worker in a movie. He gets some excellent scenes and one-liners.
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