Although The Simpsons is famous for its main characters, the show also features a huge number of supporting characters who don’t get much attention. As the longest-running American scripted prime-time TV series, it’s natural that The Simpsons has built up such a large cast over the years. Being a sitcom contributes to this too, as the show frequently introduces one-time joke characters and guest stars who appear in only a single episode.
After nearly forty years of The Simpsons, keeping track of all the characters – and picking a favorite – is a huge undertaking. While many supporting characters like Ned Flanders, Seymour Skinner, and Ralph Wiggum have gained a large following and even had episodes dedicated to their stories, there are a few equally great characters from the show’s best years who don’t get enough recognition. These three characters deserve just as much attention.
Herb Powell
Danny DeVito first appeared as Herb Powell in a Season 2 episode of The Simpsons, revealing him to be Homer’s half-brother. Unlike many of DeVito’s typical roles, Herb was initially portrayed as a kind and successful businessman. He even asked Homer to contribute to a car design, but Homer’s terrible idea ultimately led to Herb losing all his money. However, their story ended more positively in the Season 3 finale, leaving them on good terms.
Herb Powell got a loan from Homer to build a machine that could turn baby talk into understandable language. This clever invention helped him quickly rebuild his wealth and become a business success again. Years later, a joke on the show revealed he’d fallen on hard times, with his answering machine message stating he was broke. Now that The Simpsons had a shortened season, it would be a great opportunity to revisit Herb’s story and reintroduce DeVito’s character to a new audience.
Jessica Lovejoy
As a huge fan of The Simpsons, I always remember being blown away by Jessica Lovejoy. She first appeared in the episode “Bart’s Girlfriend,” and while Bart had crushes before, this was the first time a girl got a whole episode dedicated to her! And what an episode it was. Voiced brilliantly by Meryl Streep, Jessica seemed sweet at first, but it quickly became clear she was a master manipulator. She could easily wrap Bart around her finger, and she was just as good at fooling everyone else in town. It was a surprisingly dark and funny look at young love, and Jessica Lovejoy instantly became one of the show’s most memorable characters.
The storyline reaches a dramatic point when Bart nearly gets blamed for a theft – Jessica steals money from the church collection plate! Luckily, Lisa, arguably the true hero of The Simpsons, uncovers the truth. Jessica is a hilariously wicked character, a playful take on the classic “femme fatale” from film noir, and Meryl Streep is fantastic in the role. However, due to the actress’s busy schedule, Jessica hasn’t had much dialogue since her first appearance in “Bart’s Girlfriend.” Perhaps the upcoming The Simpsons Movie 2 could bring Streep back for another scene-stealing performance?
John
In Season 8’s episode, “Homer’s Phobia,” Homer becomes concerned that Bart might be gay after befriending John, a gay antique collector. The episode primarily focuses on Homer’s prejudiced beliefs and how they affect Bart, and it even won a 1997 Emmy Award for its surprisingly thoughtful handling of bigotry. While the episode’s important message about acceptance is often remembered, it sometimes overshadows what makes the episode truly great.
John Waters brilliantly plays a version of himself in this guest appearance, creating one of the most beloved characters in The Simpsons. From his subtly combative interactions with Smithers to his many memorable lines, he brings a delightful, over-the-top energy to Springfield. The show cleverly portrays his quirks in a way that makes viewers laugh with him, not at him. This makes John, alongside characters like Jessica Lovejoy and Herb Powell, one of the most charming and often overlooked figures from the show’s golden age.
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2026-04-26 03:10