A few notes on this list: In order to be considered, a character can only have appeared in one episode. The only exception is characters who later appeared in nonspeaking background roles. Also, the characters represented are from the first eight seasons only. Sorry, fans of later-season Simpsons.
25. Guy Incognito
Episode: “Fear of Flying,” Season 6
Voiced by: Dan Castellaneta
Quote: “Greetings, good man. Might I trouble you for a drink?”
What made him great: It was a one-note joke but an amazing one nonetheless — with Homer banned from Moe’s Tavern, Moe assumed his exact double Guy Incognito was Homer in disguise. In fact, Guy was just a thirsty gentleman with a really unfortunate name.
Episode: “Summer of 4 Ft. 2,” Season 7
Voiced by: Christina Ricci
Quote: “Yeah. Doing stuff sucks.”
What made her great: Erin seemed like someone who would be too cool for Lisa Simpson — and that’s exactly what Lisa thought. But once Erin learned the truth about Lisa’s nerddom, she continued to stand by her new friend, even helping with a sweet (albeit misguided) redecoration of the Simpsons’ car.
23. Chester J. Lampwick
Episode: “The Day the Violence Died,” Season 7
Voiced by: Kirk Douglas
Quote: “I’m not greedy. As long as I’ve got my health, my millions of dollars, my gold house, and my rocket car, I don’t need anything else.”
What made him great: Chester’s story was a sad one: It wasn’t until he reached the ripe old age of 103 that he got recognition for creating Itchy (and with him, cartoon violence). Though he spent years in poverty, he had expensive tastes. Who wouldn’t want a rocket car?
22. Dr. Zweig
Episode: “Fear of Flying,” Season 6
Voiced by: Anne Bancroft
Quote: “The Monkees weren’t about music, Marge. They were about rebellion, about political and social upheaval!”
What made her great: Without Dr. Zweig, Marge never could have overcome her fear of flying. And while that would have spared us countless “The Simpsons are going to [insert country here]” episodes, it would have been sad for Marge. And no, the therapist’s name is not Dr. Lowenstein.
Episode: “Simpson and Delilah,” Season 2
Voiced by: Harvey Fierstein
Quote: “My mother taught me never to kiss a fool!”
What made him great: Did Karl have a crush on Homer? It would be hard not to with Homer’s lush flowing locks. Either way, he helped Homer discover potential he never knew he had. And he kissed him on the lips, which was groundbreaking back when it happened in 1990.
20. Laura Powers
Episode: “New Kid on the Block,” Season 4
Voiced by: Sara Gilbert
Quote: “You know, if you were only old enough to grow a bad teenage moustache, I’d go out with you in a second.”
What made her great: The thing most Simpsons fans remember about Laura is that she breaks Bart’s heart — as shown in the horrifying dream sequence where she literally rips it out of his chest. But Laura was an awesome babysitter and an even better prank caller.
19. Samantha Stanky
Episode: “Bart’s Friend Falls in Love,” Season 3
Voiced by: Kimmy Robertson
Quote: “All my friends are back in Phoenix and this town has a weird smell that you’re all probably used to… but I’m not.”
What made her great: Poor, sweet Samantha Stanky. Her brief love affair with Milhouse ended tragically as she was shipped off to a French-Canadian Catholic school. As much as Milhouse loves Lisa, there’s still some hope he and Samantha will make it work one day, when they’re old enough to date.
Episode: “Brother From the Same Planet,” Season 4
Voiced by: Tress MacNeille
Quote: “Papa Homer, you are so learned.”
What made him great: It’s impossible to look into Pepi’s giant eyes and not instantly fall in love. Just try not to think about how much damage Homer did as his big brother. At least Pepi’s story had a happy ending: He got paired off with Tom, a much better role model who would never call him “Pepsi.”
17. Larry Burns
Episode: “Burns, Baby Burns,” Season 8
Voiced by: Rodney Dangerfield
Quote: “Wow, this guy is loaded. I mean sheesh. I’ve never seen a guy with a walk-in mailbox. I mean he’s rich. Hey, who am I talking to?”
What made him great: He was essentially Rodney Dangerfield blended with Mr. Burns, and that was a sight to behold. If you aren’t a fan of Rodney Dangerfield’s schtick, you probably didn’t really care for Larry. But for most comedy fans, he was a treat.
Episode: “Homer the Vigilante,” Season 5
Voiced by: Sam Neill
Quote: “Homer, old chap, well done. If anyone was going to catch me, I’m glad it was you.”
What made him great: Turns out not all old people are as useless as Abe Simpson. Molloy was an impressive cat burglar and criminal mastermind, eventually leading the whole town on a wild goose chase. But he returned Lisa’s sax, for which we’ll always be grateful.
15. Shary Bobbins
Episode: “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious,” Season 8
Voiced by: Maggie Roswell
Quote: “I’m an original creation, like Rickey Rouse and Monald Muck.”
What made her great: Even though she was a very obvious parody of Mary Poppins — no, really! — Shary Bobbins came into her own with memorable songs and a complete distaste for the Simpsons family. She also got sucked into a jet engine and died, as so many nannies do.
14. Rex Banner
Episode: “Homer vs. the Eighteenth Amendment,” Season 8
Voiced by: Dave Thomas
Quote: “Listen, rummy, I’m gonna say it plain and simple. Where’d you pinch the hooch? Is some blind tiger jerking suds on the side?”
What made him great: Clearly living in a different era, Rex Banner was never cut out for survival in Springfield. (And it’s implied he didn’t, since he ended up catapulted to his death.) Inspired by Eliot Ness, he proved a worthy adversary for a surprisingly savvy bootlegging Homer.
13. Jessica Lovejoy
Episode: “Bart’s Girlfriend,” Season 6
Voiced by: Meryl Streep
Quote: “You’re bad, and I like it.”
What made her great: Who would have guessed the daughter of Reverend Lovejoy would turn out to be such a monster? Hey, she just wanted attention. In the end, Jessica proved herself to be too cruel even for Bart, but it was nice to see him have a little romance.
12. The Spirit Guide/Space Coyote
Episode: “El Viaje Misterioso de Nuestro Jomer,” Season 8
Voiced by: Johnny Cash
Quote: “I speak of a deeper wisdom. The problem, Homer, is that the mind is always chattering away with a thousand thoughts at once.”
What made him great: He might just have been a Guatemalan insanity pepper-induced hallucination, but the Spirit Guide took Homer on a truly important journey to finding his soulmate. Plus, as voiced by Johnny Cash, he was just really, really cool.
Episode: “The Itchy & Scratchy & Poochie Show,” Season 8
Voiced by: Hank Azaria
Quote: “Right on, Mr. S!”
What made him great: Who is Roy? Where did he come from? Did he also die on the way back to his home planet? The mystery is part of his appeal — as is the fact that his entire existence was a “Fuck you” to executives who suggested The Simpsons add a new character to liven things up.
10. Michael Jackson/Leon Kompowsky
Episode: “Stark Raving Dad,” Season 3
Voiced by: Michael Jackson
Quote: “Hi, I’m Michael Jackson from the Jacksons.”
What made him great: Leon was Michael Jackson, but he wasn’t. He was voiced by Michael Jackson, but he wasn’t. (The real MJ provided his speaking voice under a pseudonym, whereas an impersonator did the song.) The point is, he wrote “Happy Birthday, Lisa,” the best birthday present ever.
9. Mindy Simmons
Episode: “The Last Temptation of Homer,” Season 5
Voiced by: Michelle Pfeiffer
Quote: “I wanna sneak in a quick nap before lunch.”
What made her great: Homer and Marge always seemed so oddly matched that it was fascinating to see what Homer’s more perfect match might look like. According to Homer, Mindy eventually hit the bottle pretty hard, which is what happens when you don’t have Marge to hold you back.
Episode: “Life on the Fast Lane,” Season 1
Voiced by: Albert Brooks
Quote: “Let it out, Marge. Laugh loud. Laugh out loud. You’ll lose weight.”
What made him great: Again, there’s just something about the characters that tempt Marge and Homer with infidelity. Jacques was such a perfect counter to Homer’s uncouthness and insensitivity. And his quote about brunch remains the standard definition of the meal.
7. Llewellyn Sinclair
Episode: “A Streetcar Named Marge,” Season 4
Voiced by: Jon Lovitz
Quote: “I am not an easy director to work for. While directing Hats Off to Hanukkah, I reduced more than one cast member to tears. Did I expect too much from fourth graders?”
What made him great: It’s unclear if Llewellyn was actually a good director — when you have material like O! Streetcar to work with, you’re bound to produce greatness. But he saw something in Marge that she didn’t see in herself, and he helped her find her creative voice.
Episode: “Homer’s Phobia,” Season 8
Voiced by: John Waters
Quote: “Well, now you don’t get any candy. … Nah, that’s cruel. Take a teensy piece.”
What made him great: It was John Waters doing John Waters. And who better but John Waters to show Homer the error of his ways? John’s passion for kitsch forced us to see the weirdly retro Simpson family in a new light. Why does Lisa wear pearls, anyway?
5. Frank Grimes
Episode: “Homer’s Enemy,” Season 8
Voiced by: Hank Azaria
Quote: “I’m saying you’re what’s wrong with America, Simpson. You coast through life, you do as little as possible, and you leech off of decent, hardworking people like me.”
What made him great: Frank Grimes — or “Grimey” as he liked to be called — pointed out something we’d all just kind of accepted up to that point: Homer Simpson is a dangerous buffoon. But the real reason Frank Grimes is a fan favorite? His hilariously abrupt death.
4. Stacy Lovell
Episode: “Lisa vs. Malibu Stacy,” Season 5
Voiced by: Kathleen Turner
Quote: “Not now. I’m too drunk.”
What made her great: It’s really all about Kathleen Turner’s pitch-perfect performance. But Stacy’s whole life was fascinating — from her dream house to her action figure ex-boyfriend. How nice that she sobered up long enough to help Lisa realize her vision.
3. Lyle Lanley
Episode: “Marge vs. the Monorail,” Season 4
Voiced by: Phil Hartman
Quote: “You know, a town with money’s a little like the mule with a spinning wheel. No one knows how he got it, and danged if he knows how to use it!”
What made him great: Charming con man Lyle Lanley was clearly modeled after Harold Hill from The Music Man. Except Lyle Lanley might actually have been a sociopath, what with leaving horrifying monorail accidents in his wake. Hey, but that song was catchy, wasn’t it?
2. Hank Scorpio
Episode: “You Only Move Twice,” Season 8
Voiced by: Albert Brooks
Quote: “Hey, look at my feet. You like those moccasins? Look in your closet; there’s a pair for you. Don’t like them? Then neither do I!”
What made him great: Because why couldn’t an evil genius supervillain also be the world’s best boss? The slow reveal that seemingly perfect Hank Scorpio is actually trying to take over the world made for a great episode, but it’s Hank’s persistent gentility that left the most lasting impression.
1. Mr. Bergstrom
Episode: “Lisa’s Substitute,” Season 2
Voiced by: Dustin Hoffman
Quote: “And for the record, there were a few Jewish cowboys. Big guys, who were great shots, and spent money freely.”
What made him great: Long, deep sigh. This is a more emotional pick than the rest — Mr. Bergstrom might not be as funny as Hank Scorpio or Frank Grimes, but he touched Lisa and all of us when he cried at Charlotte’s Web. And when he left the perfect note: “You are Lisa Simpson.”
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