The Simpsons has had no shortage of great moments, between its hilarious signs and seemingly unlimited supply of guest stars. While it’s easy to remember moments involving its most iconic characters, what’s even more amazing is how memorable they make a lot of their one-offs.
These are characters that never come back after an episode or two at most, but somehow their antics and often hilarious dialogue makes them stick around in our hearts. Here’s just a few of our favorites.
1) Hank Scorpio
Let’s get the easiest choice out of the way. Comedian Albert Brooks absolutely nailed the part of Hank Scorpio, Homer’s one-time new boss who both embodies the “cool boss” archetype and also turns out to be a Bond villain.
Every scene with Scorpio is pure gold. One minute he’s helping Homer figure out where to buy hammocks (the answer turns out to be “the hammock district”), the next he’s threatening the United Nations with a doomsday device. That Homer remains completely oblivious to his boss’ nature the entire episode makes the whole thing even funnier.
The writing is absolutely stellar here. Who didn’t laugh when Scorpio responds to Homer asking for coffee sugar by pulling some out of his pockets, complete with a comment of “Sorry it’s not in packages.” Or when he has his thugs chase down James Bond with a cry of “STOP HIM! HE’S SUPPOSED TO DIE!” Pure comedy genius.
2) Frank Grimes
“Grimey” as he’s often called by Homer (much to his dismay) is the center of one of the most darkly funny episodes of the show ever. He’s a man who could never catch a break in life, having to struggle to earn absolutely everything he’s ever gotten. His ultimate break comes when he gets hired by the nuclear power plant.
This is, of course, where he meets Homer, and is promptly shocked and upset by the fact that this incompetent oaf has had such a successful life. Not only that, but every chance Grimes has to sabotage Homer ends up blowing up in his face; their coworkers do nothing but reward Homer’s incompetence. This ultimately causes Grimes to lose his mind, at which point he grabs live wires and promptly dies.
Frank Grimes is equally hilarious and tragic because he’s a reminder that the smartest person is often not the most successful. He worked hard all of his life and achieved next to nothing, while Homer bumbles his way through everything (even Grimes’ funeral) and comes out on top. It’d be sad if Homer wasn’t so endearing.
3) Rex Banner
When Springfield brings back prohibition and the police force (particularly Chief Wiggum) refuses to do anything to enforce it, who does Mayor Quimby call in but 1930s-style supercop Rex Banner (a direct parody of Kevin Costner’s portrayal of Elliot Ness from The Untouchables).
Banner is as competent as Wiggum is bumbling, and his stark, fast-talking seriousness is often hilarious when contrasted by the sheer insanity that is the show’s cast. Even when he attempts to have a serious moment, he’s interrupted by Homer.
He ultimately proves to be far more serious than the town can stand though, and his exit is just as dramatic as his entrance; he is literally catapulted out of Springfield.
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When Homer commits insurance fraud to get a miracle hair growth drug, he is soon promoted way above his station and ends up completely lost in his new job. Thankfully, he gets the savior her needs when Karl shows up out of nowhere to apply as his assistant.
The deep-voiced, eloquent giant is practically a guardian angel to Homer. He remembers to send Marge flowers on Homer’s behalf when he’s forgotten her birthday, he teaches him how to dress, and ultimately instills in him the confidence he needs to do his job well.
When Smithers ultimately discover’s Homers fraud and threatens his job, Karl even takes the blame for his beloved boss and is fired instead, showing up one last time to give Homer words of wisdom (and smack him on the butt) before he heads off to his big presentation. We should all be so lucky to have a Karl in our lives.
Voiced by lowbrow film god John Waters, John is the infinitely charming and likeable salesman who owns a collectibles shop in the mall. After having things offered to his store by the Simpsons, he takes a liking to the family (especially Homer) and begins to spend plenty of time with them.
This turns sour for Homer, however, who is the last one of the family to realize that John is gay. While the rest of them take no issue whatsoever with this, Homer finds his masculinity threatened, and even becomes worried that John will “turn Bart gay” through spending time with the family.
John is brilliantly written and performed by Waters (just try not to hear him going “zzzzzzzzzzzzzap!”). His character both serves as an interesting perspective on the family’s antics, and as a valuable lesson for Homer not to judge someone based on their sexuality, and we love him for it.
6) Lyle Lanley
Taken straight from the pages of the play The Music Man, Lyle Lanley is a fast-talking, high-energy con artist who convinces the town to invest a surplus of money into a monorail project that he proposes. He convinces them to do this via perhaps the show’s most iconic song.
Lanley is of course lying to everybody and is skimming the money for himself, which comes to light when the monorail’s maiden voyage (where it is of course driven by Homer) goes out of control. Lanley has already fled, but when his plane has to make an emergency stop in a town he has conned before, he is cornered and presumably killed by an angry mob.
One of the many Simpsons characters ably played by the late Phil Hartman, Lyle Lanley is memorable both for his impromptu song and for being equal parts sinister and charming. He’s never without a fake smile on his face, and nearly everybody falls for it; including us! Of course, seeing him get his just desserts is also incredibly satisfying.
Who’s your favorite?