The Simpsons 10 Best OneOff Characters Ranked

The Simpsons: 10 Best One-Off Characters, Ranked

The Simpsons may have a massive cast of regulars, but it’s the amazing one-off characters that really make the show special.

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The Simpsons 10 Best OneOff Characters Ranked

For a show with such a huge cast of recurring supporting characters, The Simpsons has an awful lot of one-off characters who only show up for a single episode. In the show’s more recent seasons (the not-so-great ones), it has relied quite heavily on celebrity guest stars, and so it seems like there’s a new one-off character in every episode these days.

Since very few of them turn out to be memorable anymore, it can be easy to forget that there have been some brilliant one-off characters on this show. So, here are the 10 Best One-Off Simpsons Characters, Ranked.

10 Lyle Lanley

The Simpsons 10 Best OneOff Characters Ranked

Many Simpsons fans consider “Marge vs. the Monorail” to be the single greatest episode of the entire series – and even if you disagree that it’s the very best, you have to admit that it’s up there. In the episode, a snake oil salesman named Lyle Lanley comes to town and pitches a monorail system that will make him a boatload of money and be completely unsafe for Springfield.

Marge uncovers his plan, including the fact that he’d done it in several towns before. Phil Hartman played Lanley hilariously (as he did with all of his other Simpsons roles) as a shady guy with a smooth pitch.

9 Shary Bobbins

The Simpsons 10 Best OneOff Characters Ranked

Showrunner Al Jean has called “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious” one of the most essential episodes in The Simpsons’ history. When the stress of being a homemaker and a mother starts getting to Marge, the Simpson family brings in a magical nanny named Shary Bobbins.

At first, she’s a delight. She enjoys fixing the family’s dysfunctions through song and they start to get along. However, Shary becomes bitter as the Simpsons take advantage of her good nature and begin to ignore her advice. So, she decides that the Simpsons can’t be fixed and takes off with her flying umbrella – only to get sucked into a jet engine immediately.

8 Frank Grimes

The Simpsons 10 Best OneOff Characters Ranked

The episode “Homer’s Enemy” is controversial among Simpsons fans, because it has an uncharacteristically dark tone, but it is also considered by some circles to be an all-time great episode of the series. It opens with Frank Grimes, the unluckiest man in America, being offered a job at the nuclear plant by Mr. Burns.

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As Frank starts working at the plant, he finds that he absolutely despises Homer, both for his irritating demeanor and his inexplicable good fortune – and the fact that he’s the only one to see how annoying Homer can be drives him insane. Eventually, he accidentally kills himself, and Homer’s ineptness turns his funeral into a laughing stock.

7 Larry Burns

The Simpsons 10 Best OneOff Characters Ranked

Rodney Dangerfield was the perfect casting to play Mr. Burns’ long-lost son, Larry, in the season 8 episode “Burns, Baby Burns.” This is mainly because the writers appreciated Dangerfield’s comic talent and wrote the character specifically for him, so let’s rephrase: a Rodney Dangerfield-type character (a brash, loud-mouthed charmer) was the perfect persona for Mr. Burns’ son, to contrast with his quiet cynicism.

The character was designed to look like a cross between Mr. Burns and Dangerfield himself, with a larger-than-life presence and a pointy nose. It was an apt pairing of guest star and character to ensure that both are memorable.

6 Laura Powers

The Simpsons 10 Best OneOff Characters Ranked

Bart gets his heart broken in the season 4 episode “New Kid on the Block,” when Marge’s friend’s daughter comes to babysit him. Bart instantly falls in love with Laura – played by Sara Gilbert, who is now best known as The Big Bang Theory’s Leslie Winkle – because she’s the coolest person he’s ever met and they have a lot in common.

However, Bart is devastated to discover that she already has a boyfriend. And not only that, it’s Jimbo! In the end, Bart gets revenge by prank-calling Moe and giving his name as “Jimbo” and his home address, so that Moe would attack Jimbo and embarrass him in front of Laura.

5 Leon Kompowsky

The Simpsons 10 Best OneOff Characters Ranked

Leon Kompowsky is better known as Michael Jackson, since that was who he spent the episode claiming to be. He looked nothing like Jackson, but he did have his voice. The episode was called “Stark Raving Dad” and it began with Homer being wrongfully incarcerated in a mental asylum.

There, he met Leon, who claimed to be the King of Pop. Homer ended up bringing him home and he helped Bart to write a song for Lisa’s birthday. There were plans for a sequel episode in which Leon would impersonate Prince, and Prince himself was on board, but the deals couldn’t be put together.

4 Rex Banner

The Simpsons 10 Best OneOff Characters Ranked

In the episode “Homer vs the Eighteenth Amendment,” when Springfield’s local government reintroduced the prohibition laws and Homer started up an illegal bootlegging operation, Rex Banner was the tough-as-nails detective brought in to crack his illicit booze-shilling ring.

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Dave Thomas played him as a straight-talking, no-nonsense cop to contrast his personality with the absurdity going on around him. The episode is summed up nicely by Homer’s immortal line: “To alcohol! The cause of…and solution to…all of life’s problems.” But it’s Rex Banner who takes the title of the episode’s MVP. Every single one of his lines is hysterical, and he’s established and fleshed out almost immediately.

3 Jessica Lovejoy

The Simpsons 10 Best OneOff Characters Ranked

Played by Meryl Streep, Reverend Lovejoy’s daughter Jessica made a perfect match for Bart. Since she never lets her bad side show and she’s the daughter of the local preacher, she seems like the least suspicious person in Springfield. And that’s why, when she does something wrong, Bart is the first person to get the blame.

Jessica is a classic example of looking like an innocent flower, but being the serpent under it. She was a classic femme fatale character and an ideal romantic interest for Bart. So, it’s a shame that she only ended up appearing in one episode.

2 Mr. Bergstrom

The Simpsons 10 Best OneOff Characters Ranked

Played by Dustin Hoffman in the episode “Lisa’s Substitute,” Mr. Bergstrom wasn’t a particularly funny character beyond being the straight man to Homer as the father figure in Lisa’s life and a few references to Hoffman’s previous work. However, he was a significant one.

The impact that he had on Lisa’s character development can still be seen today. He encouraged her to believe in herself and not to get too down because she didn’t have many friends or because she was doubting her own abilities, and he managed to say it all with a simple handwritten note: “You are Lisa Simpson.”

1 Hank Scorpio

Hank Scorpio was the supervillain who gave Homer a job in the episode “You Only Move Twice.” He was played by Albert Brooks, a recurring guest star who has appeared in more episodes of The Simpsons than any other guest star (always credited as “A. Brooks”), and his bubbly enthusiasm and nonchalant approach to hostage negotiations immediately struck a chord with the show’s diehard fans.

From sending a laser beam up between a gentleman spy’s legs to stopping by the Simpsons’ house and tossing his sneakers in the middle of running a marathon, Hank Scorpio is always unpredictable, bursting with energy, and utterly hilarious.

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