The 5 Best and 5 Worst Simpsons Characters of All Time

Thousands of characters have appeared on The Simpsons throughout its 30+ season run. Who would you pick as the best and worst?

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When The Simpsons first aired in 1989, it immediately took the world by storm. It’s now on its 32nd season—as of this writing—and the family-friendly animated TV sitcom has introduced roughly 3,650 characters throughout fictional Springfield.

There have been celebrity cameos, supernatural villains, and town regulars with witty catchphrases. If you’ve watched more than a handful Simpsons episodes, you probably have your favorites and the ones whom you hate (or just find irritating).

We’re going to explore these characters and list the ones whom we think are worthy of being in the Best 5 and Worst 5.

But we aren’t including any characters from the actual Simpsons family. Why? Because they’d take up all the room!

Homer and Bart are the funniest and most quotable characters. Lisa is a sarcastic and progressive queen. Marge is an absolute sweetheart. And Maggie? She’s the coolest baby you’ve ever seen.

We love the main characters the most because we know them the most—more than anyone else on the show. To keep things fair, we’re giving the rest of Springfield a chance to shine.

Here we go! We present the best and worst characters from the entire series of The Simpsons.

The Best Simpsons Characters

5. Sideshow Bob

The recurring gag of stepping on a rake. His obsession with killing Bart. Sideshow Bob is more than just a character—he’s a punchline.

Sideshow Bob has starred in 14 of his own episodes, beginning with “Krusty Gets Busted” in season one. After framing Krusty the Clown for robbery and taking over his show, Bart exposes Sideshow Bob’s crimes and gets him arrested. Fast-forward a few seasons and he’s writing “Die Bart Die” in his own blood.

Why do we love this homicidal maniac? Well, he’s classically British and boasts a dry sense of sarcastic humor and vast intellect. Yet, for all his brains, he still ends up getting hit in the face with rakes.

4. Bleeding Gums Murphy

Not many recurring characters actually die in The Simpsons (or even age, for that matter). But one character does die, and that character is Bleeding Gums Murphy.

Implied to be the lost brother of Dr. Hibbert, Bleeding Gums Murphy only appeared in two episodes (three if you count the clip show episode in season seven). And yet, we still mourn him deeply because of the strong connection he shared with Lisa early in the show.

Lisa is an immensely smart and geeky artist with a passion for jazz, but not many real friends or strong connections. So when she meets a lonely failed jazz musician in Bleeding Gums Murphy, her passions for music and life are reignited.

He’s more than an idol; he’s a friend. One who appears in the clouds after his death for one last moonlit jam with Lisa.

3. Milhouse Van Houten

Milhouse’s chief role in The Simpsons is to be Bart’s best friend, sidekick, and slave. Bart’s wish is his command—but on the rare occasion when Milhouse leaves his side, we see that Bart needs and loves him more than he lets on.

Milhouse is a wimp. A slightly annoying and sickness-prone wimp who’s targeted by the school bullies. We shouldn’t love him, but we do. Without Milhouse, where would Bart be?

Plus, he’s unintentionally funny and has some of the best quotes of the show (“Everything’s coming up, Milhouse!”). He’s goofy to look at, and we can’t help but feel sorry for his awkward little soul, not to mention his unrequited love for Lisa.

2. Principal Seymour Skinner

An ex-Army veteran who still lives with his mom (who’s coincidentally one of the worst characters on the show), Principal Skinner is as square as they come.

He doesn’t seem to grasp the concept of sarcasm, taking everything straight on. And he’s often the subject of ridicule. Whether it’s Bart, Superintendent Chalmers, or his own mother, there’s always someone on Skinner’s case.

Occasionally we do see glimpses into the dark corners of his mind, traumatized by his days in Vietnam. But usually he’s a happy fellow who’s simple-minded but good of heart. He’s always trying his best to please people, who often take advantage of him.

Although the creators of The Simpsons tried to erase his character development in season nine’s “The Principal and the Pauper,” most fans agree to ignore that this episode even exists.

1. Mr. Bergstrom

Mr. Bergstrom only appeared in one episode and is the celebrity cameo of Dustin Hoffman. Unfortunately, The Simpsons has since been saturated with so many famous voices that cameos don’t feel special.

But Mr. Bergstrom comes from an era when celebrity cameos were indeed still special, appearing all the way back in season two’s “Lisa’s Substitute.” When Miss Hoover is off sick from teaching, Mr. Bergstrom comes in as Lisa’s inspiring substitute. Bounding in with his cowboy hat and guitar, Lisa instantly falls for him—and so do we.

Mr. Bergstrom is gentle of heart, crying over Little Women and motivating Lisa to follow her dreams. When he eventually has to leave for Capital City, Lisa weeps at the train station, running after the father figure Homer sometimes failed to be.

Before leaving, he writes a note for Lisa to read any time she feels alone. It says: “You are Lisa Simpson.” Cue the waterworks.

Honorable mentions for best Simpsons characters: Otto, Lenny and Karl, Hank Scorpio, Lionel Hutz, Ned Flanders, Mrs. Krabappel, and Apu.

The Worst Simpsons Characters

5. Rod and Todd Flanders

While Milhouse is meek and whiny, Rod and Todd are on another level—which isn’t surprising given their sheltered upbringing under the devout Christian Ned Flanders.

Rod and Todd’s high-pitched voices and inability to have fun make them the polar opposite to our family-favorite Bart Simpson. The funniest thing to come out of them is “I don’t want any damn vegetables” from Todd’s mouth.

Todd is unbelievably impressionable (much to Ned’s chagrin) and Rod is usually found praying somewhere. Their favorite hobbies? Clapping and being quiet. Snore…

4. Dr. Marvin Monroe

The most irritating thing about Dr. Marvin Monroe—and the main reason he’s on this list—is his voice. It’s shrill and nasal as he spouts rubbish about his unusual views on psychology.

Marvin Monroe is a psychiatrist who first appeared in season one’s “There’s No Disgrace Like Home” where he electrocutes the Simpsons family as a method of therapy. He’s appeared in eight total episodes, and his current status is unknown.

Many fans believe Dr. Marvin Monroe to be dead on account of lucid appearances on the show. Season seven’s “The Simpsons 138th Episode Spectacular” heavily implied his passing—but after a long absence, he returned to review Marge’s book and claimed to have been “very sick.” Later in season 29, he’s conjured as a ghost.

3. Comic Book Guy

There are characters who have funny sarcasm (like Sideshow Bob and Lisa), and then there are characters who are just rude… like Comic Book Guy. He’s a nerd who believes he’s better than everyone else, despite spending his days scarfing down food and watching movies.

He knows everything there is to know about superheroes and mythology, but nothing about real life. He overcharges little kids for bits of paper and has a negative opinion or comment for anything that isn’t fictional memorabilia.

A proud geek and monomaniac, Comic Book Guy obsesses over his collections to the point of having a heart attack at one point. Sometimes he’ll make a valid point, but his arrogant and pessimistic delivery is a vibe-killer for sure.

2. Agnes Skinner

“Seymour!” Agnes screams, calling out for her son Principal Skinner so she can order him about. Agnes Skinner incessantly moans at, demands of, and belittles Seymour, all while expecting to be treated as if she were royalty.

Like most of the worst characters on The Simpsons, Agnes never has a positive thing to say. She’s an exacting, bitter old woman who treats most people like dirt. She’s been married four times—mostly to tow truck drivers—yet criticizes Seymour’s own love life.

Most of Springfield is partially afraid of Agnes, despite her looking so frail and elderly. She’s feisty and, surprisingly, likes to sleep around, controlling every man that comes into her life.

It’s down to Seymour to take back his own life—he’s a fully grown man, after all—but we’d still like Agnes to cut him a little slack.

1. Helen Lovejoy

Nobody likes a gossip, and Helen Lovejoy is the biggest gossip in Springfield. The only other thing she does besides spreading rumors is screaming “Won’t somebody please think of the children!”

Helen is the wife of disillusioned Reverend Lovejoy, whom she constantly nags. She’s always talking about her “friends” behind their back—including our beloved Marge Simpson.

It’s hard to think of any redeeming qualities that aren’t overshadowed by her judgmental nature. She uses people’s secrets as leverage over them. She’s openly Conservative. She even gangs up with the other housewives to kick Marge out of business. Poor Marge!

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