While The Simpsons has plenty of iconic characters in the show’s main cast, the series also has a gigantic pileup of supporting characters who rarely get their due. Since The Simpsons is now officially the longest-running US scripted prime-time TV series ever made, it makes sense that the show has amassed a cast of thousands. The fact that the series is also a sitcom doesn’t help, as it means that The Simpsons has introduced countless one-off gag characters and one-episode guest stars throughout its decades on the air.
With almost four decades of The Simpsons to date, it is a mammoth task to even catalogue the show’s characters, let alone choose a favourite among them. However, there are a few notably great characters from the Golden Age of The Simpsons who rarely get their due in discussions of the series. Some supporting stars, like Ned Flanders, Seymour Skinner, or Ralph Wiggum, have become so popular in the show’s fandom that they have numerous episodes focused on their character arcs. However, this trio of sorely underrated characters have not yet received the same treatment.
Originally introduced in season 2’s “Oh Brother, Where Art Thou?”, Danny DeVito’s Herb Powell is Homer’s half-brother. A successful businessman when he was first introduced, Powell was a far cry from the shady figures DeVito often plays onscreen. The sweet, ambitious businessman even asked Homer to help him design a new car, only for Homer’s moronic car concept to end up bankrupting Powell entirely. Fortunately, season 3’s finale “Brother, Can You Spare Two Dimes?” wrapped up the pair’s shared story on a lighter note.
Powell borrowed seed money from Homer to regain his fortune through a device that converted the babbling of babies into coherent speech. This adorable gadget soon saw Herb rise back to the top of the business world, although a throwaway joke decades later in season 24 saw his answering machine message say, “I’m poor again.” While this was a funny nod to Homer’s family, after The Simpsons season 37’s early end, the show should revisit Herb’s storyline in earnest and reintroduce DeVito’s character to a new generation of viewers.
Voiced by screen legend Meryl Streep, Jessica Lovejoy was first introduced in season 6, episode 7, “Bart’s Girlfriend.” Despite the title, Jessica wasn’t Bart’s first love interest ever, but she was the first to earn an entire episode of her own, and what an episode it was. A hilariously dark story of manipulation and young love, “Bart’s Girlfriend” reveals that Lovejoy is a manipulative hell raiser beneath her sweet facade, and she is just as capable of wrapping Bart around her little finger as she is of fooling her father and the townspeople.
This culminates in a brutally dark plot where Bart is almost framed when Jessica steals the church collection plate money until the true hero of The Simpsons, Lisa, reveals the truth. Essentially a middle school spin on the classic film noir trope of the femme fatale, Jessica is as comically evil a character as The Simpsons ever introduced, and Streep is a scene-stealing blast in the role. Naturally, the star’s busy schedule means that, while Jessica often appears onscreen, her dialogue has been almost non-existent since “Bart’s Girlfriend.” Maybe 2027’s upcoming The Simpsons Movie 2 could tempt Streep into returning?
Season 8, episode 15, “Homer’s Phobia,” sees Homer start to worry that Bart could be gay after the family befriends the local gay antique collector, John. As the title implies, “Homer’s Phobia” mostly concerned itself with addressing Homer’s homophobia and the ways it impacted Bart’s upbringing, with the show winning the 1997 Primetime Emmy Award for Outstanding Animated Program for this unexpectedly sensitive portrayal of bigotry brought to light. However, as valuable as the episode’s progressive social commentary was, its cultural significance often overshadows the best part of “Homer’s Phobia.”
Gay icon and legendary filmmaker John Waters plays John in the outing, and the camp antiquarian is one of the show’s most memorable creations. From his passive-aggressive confrontation with Smithers to his endlessly quotable lines, John is a welcome injection of high camp into the world of The Simpsons, and the show consistently ensures that viewers are laughing affectionately with his eccentricities rather than turning him into a target for mean-spirited mockery. As a result, John joins Jessica Lovejoy and Herb Powell as one of the most underrated The Simpsons characters from the show’s classic era.
