3 Classic Simpsons Characters Who Quietly Stole the Show

For a show that has been on the air since what feels like the dawn of time, The Simpsons has an absurd number of characters. The main cast is iconic, sure, but the bench is deep. Decades of one-off gag players and guest stars will do that to a sitcom. And while folks like Ned Flanders, Principal Skinner, and Ralph Wiggum got whole arcs built around them, a few standouts from the show’s golden-age years never really got their turn in the spotlight. Let’s fix that.

• Herb Powell

  Danny DeVito shows up in season 2’s 'Oh Brother, Where Art Thou?' as Homer’s long-lost half-brother, and he is not the kind of character you expect DeVito to play. Herb is an actually competent, actually kind executive who makes the fatal mistake of letting Homer design a car. That 'Homer car' immediately detonates his company and his fortune. It ’s brutal.

  Season 3’s finale, 'Brother, Can You Spare Two Dimes?', throws him a lifeline. Herb borrows seed money from Homer, invents a device that turns baby babble into understandable speech, and rides that adorable idea right back into the black. It’s one of the show’s rare feel-good rebounds.

  "I’m poor again."

  Years later, a throwaway season 24 gag undercuts all that with Herb’s answering machine cheerfully admitting he’s broke again. Funny, yes, but it would be nice if the show actually revisited him for real and brought DeVito back for an update instead of just dropping punchlines.

• Jessica Lovejoy

  Meryl Streep voicing a chaos gremlin in pigtails is exactly the kind of curveball this show used to live on. Introduced in season 6, episode 7, 'Bart’s Girlfriend', Jessica isn’t Bart’s first crush, but she’s the first to get a full showcase. Under the pastor’s-kid halo is a world-class manipulator who can con Bart, her dad, and the entire town without breaking a sweat.

  The episode goes dark in a very funny way: Jessica steals the church collection money and nearly pins it on Bart, until Lisa (as usual) solves the case. It plays like a middle school take on a classic femme fatale, and Streep absolutely feasts on the role.

  Here’s the catch: Jessica pops up in the background now and then, but she basically hasn’t had lines since 'Bart’s Girlfriend' — the perils of booking Meryl Streep. If the long-chatted-about Simpsons Movie 2 that people keep floating for 2027 really happens, maybe that’s the carrot to get her back.

• John

  Season 8’s 'Homer’s Phobia' is one of the series’ sharpest balancing acts: it’s a very funny episode that also calls Homer out on his homophobia after the family befriends John, a local gay antique dealer. The outing won the 1997 Primetime Emmy for Outstanding Animated Program, and it earned it.

  Part of why it works: John is played by filmmaker and camp legend John Waters, who turns a single-episode guest role into a capital-C Character. He’s got chilly banter with Smithers, he’s endlessly quotable, and the humor is with him, not at him. The show treats him with affection, and he steals the episode without turning into a punchline.

With nearly four decades of Springfield under its belt and the distinction of being the longest-running US scripted prime- time series, The Simpsons is so stuffed with characters that even keeping a list is a headache. But these three are overdue for real returns. They were great then, and there’s plenty more story left if the show actually gives them the room that Flanders, Skinner, and Ralph have enjoyed for years.