The Simpsons: 10 Guest Star Characters Who Would've Been Perfect As Permanent Springfield Residents

The Simpsons has featured plenty of guest stars over the years, but these cameo roles should have become more reoccurring figures in the series. The Simpsons famously has relied on a tight-knit cast for the past thirty-six seasons, with many of the show’s characters played by just a handful of performers. The Simpsons‘ deep bench of guest stars typically only appears for an episode. However, there are some guest actors who’ve become prominent recurring members of the show, such as Kelsey Grammer’s Sideshow Bob and Marcia Wallace’s Edna Krabappel.

However, there are some guest star characters who only made one or two speaking appearances that, if they’d been given the chance, could have been ideal additions to the dynamics of The Simpsons‘ world. They could have expanded the show’s satirical potential, set up new rivalries around town, and even been consistent love interests or rivals to the central cast. While each of these characters was memorable in their brief appearances in The Simpsons’ 36 seasons, these ten would have been perfect recurring characters in the show.

10

Herb Powell (Danny DeVito)

Heb Powell Debuted In Season 2’s “Oh Brother, Where Art Thou?”

Herb Powell is the exact kind of minor character from The Simpsons who would have made an ideal recurring character in the show. Herb is Homer’s long-lost half-brother, who grew up to become a wealthy and successful car manufacturer. His connection to the family would have made him an ideal figure to bring back, highlighting his bond with the rest of the family. He could have served as a direct contrast to other characters in the show, providing a natural foil to Mr. Burns with his wealth or Patty and Selma through his family connections.

The show never got the chance to really pair him up with his father, Abe, which could have been a great source of dramatic potential. In particular, Herb’s relationship with Homer could have brought a compelling new shade to Homer’s happy-go-lucky approach to life and frequently despondent self-reflection, serving as an ideal reflection for Homer to bounce off in future stories. Herb might get the chance to return though, as DeVito has been confirmed to appear in season 36.

9

Jessica Lovejoy (Meryl Streep)

Jessica Lovejoy Debuted In Season 6’s “Bart’s Girlfriend”

The daughter of Reverend Lovejoy and his wife Helen, Jessica proved to be a much more troublesome girl than anyone could have expected when she debuted in season 6. Quickly developing a romance with Bart after discovering his love for pranks and chaos, Jessica’s willingness to cross lines even Bart wouldn’t might have made her an ideal addition to the younger cast of Springfield. She could have easily been an antagonist in episodes, highlighting her dangerous edge.

Jessica could have also been a compelling occasional romantic love interest for Bart. She also could have become a dedicated foil to Lisa that would have become especially relevant in light of Lisa’s later spiritual journey. Jessica had great potential as a disruptive force for the Lovejoys as well, giving them a chance to potentially find conflict (or even empathize) with Homer and Marge over the troubles of raising a “bad kid,” giving the two couples more excuses to be paired up in episodes.

8

Princess Penelope (Anne Hathaway)

Princess Penelope Debuted In Season 21’s “Once Upon a Time in Springfield”

Princess Penelope brought some fresh life to Krusty’s corner of Springfield, and could have continued to do so beyond her debut episode. Introduced as a means of attracting girls to his audience, Penelope’s instant success was a great way to force Krusty to feel genuine jealousy and drama. However, their unexpected romance helped highlight the internal good hidden beneath the clown, something that could have been expanded upon in other episodes.

If Penelope had been a more recurring character in the show, the series could have mined their relationship and competing careers for plenty of gags poking fun at the entertainment industry. It would have also been a good chance for the show to highlight the changing standards of pop culture, as the younger star could have forced Krusty to confront his dated act with a softer touch than other episodes (like season 9’s “The Last Temptation of Krust”) did. More than anything, her soft side could have given Krusty a consistent innocent foil contrasting against his typically sleazy elements.

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7

Allison Tyler (Winona Ryder)

Allison Tyler Debuted In Season 6’s “Lisa’s Rival”

Allison Tyler might be one of The Simpsons‘ most underused concepts, as Allison’s debut episode “Lisa’s Rival” proved how she could have been the ideal character to pair up alongside Lisa. A sweet-natured and quick-witted girl, Allison presents a unique challenge to Lisa as the other put-upon brainiac in Springfield. The friendship they developed at the end of the episode ultimately didn’t really go anywhere, which is a shame.

Allison could have become a Milhouse-like figure to Lisa, with a clear enough personality to stand out as opposed to characters like Janey, who rarely are given lines and much in the way of personality. Her ability to bring out an uglier, more competitive side of Lisa would be explored with other minor characters in the show (such as Eva Longoria’s Isabel in season 25’s “The Kid Is All Right). However, Allison’s family being successful academics were also a potential goldmine from a storytelling perspective, especially if they had been put up alongside characters like Homer.

6

Ruth Powers (Pamela Reed)

Ruth Powers Debuted Season 4’s “New Kid on the Block”

Of all the minor guest characters The Simpsons could have turned into more consistent recurring figures in Springfield, Ruth Powers is the one that feels like the most natural fit into the show. Introduced as a new neighbor to the Simpsons, Ruth was an ideal supporting character for Marge. Ruth worked as a solid contrast compared to her, an embittered single mother who could drag Marge out of her shell.

Although Ruth has had a few return appearances in The Simpsons since her debut (and was eventually revealed to have been sent to prison for a time, explaining her absence), it’s a shame Rith didn’t become a more consistent character in the spotlight. She could have continued to be Marge’s primary friend, serving as a natural storytelling device to force Marge out of the house. She could have also been a perfect rebellious contrast to the uptight Ned Flanders, a dynamic the show never really got to explore in her brief appearances.

5

Thelonius Monk (Frankie Muniz)

Thelonius Debuted In Season 12’s “Trilogy Of Error”

While Bart has acquired a number of supporting characters and love interests over the years, Lisa has had fewer concrete connections. A potentially compelling one would have been Thelonius, the brainy student at West Springfield Elementary who Lisa fell head over heels for in season 12. As a fellow geeky student, he could have served as a contrast to the more comically pathetic Milhouse, while expanding Lisa’s social circle in a sweet way.

Thelonius could have been another natural target of the bullies who terrorize Springfield, or could have naively factored into some of Bart’s plans. Thelonius being a recurring character would have also been an easy excuse for the show to shift focus to other schools around Springfield, giving Superintendent Chalmers and Principal Skinner more focus. Thelonius being perfect for Lisa but always out of reach due to other circumstances could have been a funny contrast to Milhouse’s efforts to woo her, and set him up as a natural rival to Nelson for Lisa’s affections.

4

Gina (Sarah Michelle Geller)

Gina Debuted In Season 15’s “The Wandering Juvie”

Gina was quietly one of Bart’s most interesting love interests in The Simpsons, and was quietly a potentially perfect addition to the show. As a genuinely troubled girl who developed an unexpected bond with Bart, Gina would have been an interesting foil to him going forward. “The Wandering Juvie” pokes fun at the tension she could have discovered with Lisa, which could have given the latter her own version of Nelson.

Gina could have also fit in alongside bullies like Nelson and worked perfectly well alongside Shauna, who has received more focus in recent seasons of The Simpsons. Going in and out of juvie could have naturally explained her absences between episodes, allowing her to appear whenever the show found use for her without necessarily shifting her into speechless background roles like Jessicaor Allison. Gina could have brought a lot to Springfield, but only ever got a minor cameo after her debut episode.

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3

Bode Wright (Pete Holmes)

Bode Debuted In Season 31’s “Warrin’ Priests” Two-Parter

One of the more recent additions to The Simpsons universe, Bode’s kind personality and unique perspective made him an ideal addition to Springfield. His quick connection with Lisa was an encouraging one, giving her a sweet mentor figure for once. His open and accepting approach to religion served as a direct contrast to characters like Reverend Lovejoy and Ned Flanders, the latter of whom had a memorable face-off with Bode that could have easily been expanded into other episodes.

Bode being a uniquely moral figure in Springfield could have made him someone the entire cast could have bounced off of, especially during the frequent crises that erupt across the town. Although Bode was specifically written out of the show at the end of his story, he could have easily fit into the overall structure of Springfield as a spiritual guide. He would have been a compelling source of kindness in a town often defined by cartoonishly harsh impulses.

2

Taffy (Kristen Schaal)

Taffy Debuted In Season 22’s “Homer Scissorhands”

A fifth-grader who develops an unexpected bond with Milhouse, Taffy could have offered a particularly unique addition to the younger cast of The Simpsons that her single appearance in the show couldn’t quite match. While Milhouse has been given other love interests before her, Taffy being recognized as a cool kid in a different class could have been an easy way for The Simpsons to expand the cast of characters at Springfield Elementary. Taffy could have been an interesting foil to Bart, especially if they’d actually gotten along.

Taffy’s clear dislike for Lisa could have been explored further, turning the two into genuine rivals outside of their competing interest in Milhouse. Like Allison, more exploration of Tammy’s family could have also been well-served as a contrast to other married couples in Springfield, even beyond Homer and Marge. Tammy was a sweet character who could also deliver a genuinely cutting analysis of people around her, potentially even setting her up as someone who could work with Lisa even while harboring a dislike for her.

1

Ray Patterson (Steve Martin)

Ray Debuted In Season 9’s “Trash Of The Titans”

Ray Patterson is the most underutilized concept The Simpsons has ever introduced, effectively setting up the anti-Homer in the best way possible. While there have been plenty of other characters who’ve outright disliked Homer (such as Frank Grimes), Ray being a functionary member of the Springfield city government and all-around a regular guy allowed him enough authority and distance from Homer that he could have been a recurring antagonist or even reluctant ally without losing his cool as Grimes did.

Effectively a straight-man in the absurdist comedy world of The Simpsons, Steve Martin’s deadpan disbelief and vindictive glee in “Trash of the Titans” could have been a perfect contrast to the comically corrupt Mayor Quimby or the easily distracted Homer, especially if he’d found other positions around Springfield after refusing to retake his old job at the end of his episode. Ray would have been a great character to pair up with almost any of the goofy characters found in The Simpsons, and would have been an ideal addition to the show on a more recurring basis.

The Simpsons

4.5

The Simpsons is a long-running animated TV series created by Matt Groening that satirically follows a working-class family in the misfit city of Springfield. Homer, a bit of a schmoe who works at a nuclear power plant, is the provider for his family, while his wife, Marge, tries to keep sanity and reason in the house to the best of her ability. Bart is a born troublemaker, and Lisa is his super-intelligent sister who finds herself surrounded by people who can’t understand her. Finally, Maggie is the mysterious baby who acts as a deus ex machina when the series calls for it. The show puts the family in several wild situations while constantly tackling socio-political and pop-culture topics set within their world, providing an often sharp critique of the subjects covered in each episode. This series first premiered in 1989 and has been a staple of Fox’s programming schedule ever since.

Cast

Tress MacNeille
, Julie Kavner
, Harry Shearer
, Pamela Hayden
, Nancy Cartwright
, Hank Azaria
, Dan Castellaneta
, Yeardley Smith

Release Date

December 17, 1989

Seasons

35

Network

FOX

Franchise(s)

The Simpsons