25. Snake

Memorable Quote: “Yoink!”

Random Trivia: Robert “Snake” Jailbird was a professor of archaeology before turning to a life of crime.

24. Rich Texan

Memorable Quote: “Son, I represent a group of oil tycoons who make foolish purchases. We already bought us a stained glass bathrobe, and the world’s fattest racehorse! And now, we need your ice man.”

Random Trivia: The Rich Texan has an heiress daughter named Paris Texan.

23. Mayor Quimby

Memorable Quote: “All right, settle down, people. We are all upset by Mr. Burns’ plan to block out our sun. It is time for decisive action! I have here a polite but firm letter to Mr. Burns’ underlings who, with some cajoling, will pass it along to him or at least give him the gist of it.”

Random Trivia: The character of “Diamond” Joe Quimby is based in part on “Diamond” Jim Purcell, a corrupt police chief during the 1950s in Matt Groening’s hometown of Portland.

22. Fat Tony

Memorable Quote: “I am not so much disappointed, as I am blinded with rage.”

Random Trivia: Fat Tony is a competent violinist, as seen in the episode “Insane Clown Poppy.”

21. Waylon Smithers

Memorable Quote: “Uh, no, they’re saying ‘Boo-urns! Boo-urns!’”

Random Trivia: In Smithers’ first appearance (”Homer’s Odyssey”), he was accidentally made African-American by the animation studio. With tongues planted firmly in cheek, the producers insist that Smithers had just returned from a Caribbean vacation prior to the episode and should be considered “suntanned.”

20. The Sea Captain

Memorable Quote: “Yarr, it begins. The dolphins are upon us and only this old sea dog knows how to stop — Yarr!” (two dolphins jump out of the water and rip him apart)

Random Trivia: The Sea Captain’s actual name is “Captain” Horatio McAllister. On separate occasions, he has admitted to not being an actual captain, as well as claiming to “hate the sea and everything in it.”

19. Chief Wiggum

Memorable Quote: “This is Papa Bear. Put out an APB for a male suspect, driving a…car of some sort, heading in the direction of, uh, you know, that place that sells chili. Suspect is hatless. Repeat, hatless.”

Random Trivia: Clancy Wiggum became Springfield’s Chief of Police when the former Chief got fed up with the job and decided to give his badge to the next person he met (i.e. Wiggum).

18. Grampa Simpson

Memorable Quote: “Now, my story begins in nineteen-dickety-two. We had to say ‘dickety’ ’cause the Kaiser had stolen our word ‘twenty.’ I chased that rascal to get it back, but gave up after dickety-six miles…”

Random Trivia: In addition to being a member of the secretive Stonecutters, Grampa Simpson is also an Elk, a Mason, a Communist, and President of the Gay and Lesbian Alliance.

17. Disco Stu

Memorable Quote: “Disco Stu likes disco music.”

Random Trivia: Stu had a budding career as a sea captain (calling himself “Nautical Stu”) before Marge introduced him to disco music.

16. Itchy & Scratchy

Memorable Quote: “They fight! And bite! They fight and bite and fight! Fight fight fight! Bite bite bite! The Itchy and Scratchy Show!

Random Trivia: In the Simpsons universe, Itchy and Scratchy first appeared together in a 1928 cartoon short titled “Steamboat Itchy.”

15. Groundskeeper Willie

Memorable Quote: “There’s nary an animal alive that can outrun a greased Scotsman.”

Random Trivia: Willie’s archenemy is the Irish Groundskeeper Seamus.

14. Lenny and Carl

Memorable Quote: “You know, I was hexed by a troll once and a leprechaun cured that right up.”
“Hey, you know what’s even better is Jesus. He’s like six leprechauns!”
“Yeah, but a lot harder to catch. Go with the leprechaun.”

Random Trivia: Both Lenny and Carl hold Masters of Physics degrees.

13. Professor Frink

Memorable Quote: “Unshrink you? Well that would require some sort of a ‘re-bigulator,’ which is a concept so ridiculous it makes me want to laugh out loud and chortle…but, aaahh, but not at you, O holiest of Gods, with the wrathfulness and the vengeance and the bloodrain and the ‘Hey, hey, hey — it hurts me!’”

Random Trivia: Professor Frink is named after John Frink, a Simpsons writer and producer.

12. Nelson Muntz

Memorable Quote: “Shoplifting is a victimless crime. Like punching someone in the dark.”

Random Trivia: Nelson once attended Space Camp with classmate Martin Prince, and the two became close friends. Nelson had to abandon the friendship upon returning to school, however, in order to maintain his “bad boy” image.

11. Cletus the Slack-Jawed Yokel

Memorable Quote: “Hey, you know what? I could call my ma while I’m up here. HEY, MA! Get off the dang roof!”

Random Trivia: A partial list of Cletus Del Roy Spuckler and Brandine’s children includes: Tiffany, Heather, Cody, Dylan, Dermot, Jordan, Taylor, Brittany, Wesley, Rumer, Scout, Cassidy, Zoe, Chloe, Max, Hunter, Kendall, Caitlin, Noah, Sasha, Morgan, Kyra, Ian, Lauren, Q-Bert, Phil, Condoleezza Marie, Rubella Scabies, Gummy Sue, Birthday, Crystal Meth, Dubya, Incest, International Harvester, Jitney, and Witney.

10. Krusty the Clown

Memorable Quote: “Kids, we need to talk for a moment about Krusty Brand Chew Goo Gum-Like Substance. We all knew it contained spider eggs, but the hantavirus? That came out of left field. So, if you’re experiencing numbness and/or comas, send five dollars to: Antidote, P.O. Box…”

Random Trivia: Krusty once hosted the Krusty Komedy Klassic (KKK) at the Apollo Theater in Harlem, New York. Needless to say, the show wasn’t a success.

9. Moe Szyslak

Memorable Quote: “Well, why don’t you invite him over to dinner? Turn him from an enemy into a friend. Then, when he’s not expecting it… Bam! The ol’ fork-in-the-eye!”

Random Trivia: Before becoming a bartender Moe played “Smelly” on The Little Rascals, as well as pursuing a professional boxing career — initially under the name “Kid Gorgeous,” followed by “Kid Presentable,” “Kid Gruesome,” and eventually “Kid Moe.”

8. Apu Nahasapeemapetilon

Memorable Quote: “Thank you, come again!”

Random Trivia: Apu and his wife Manjula are the proud parents of octuplets: Anoop, Uma, Nabendu, Poonam, Priya, Sandeep, Sashi and Gheet.

7. Milhouse

Memorable Quote: “We started out like Romeo and Juliet, but it ended up in tragedy.”

Random Trivia: Milhouse is one of only a small handful of Simpsons characters (including his parents) drawn with eyebrows.

6. Troy McClure/Lionel Hutz (tie)

Memorable Quotes: “Hi, I’m Troy McClure. You may remember me from such self-help tapes as Smoke Yourself Thin and Get Some Confidence, Stupid!”

“Homer, I don’t use the word ‘hero’ very often, but you are the greatest hero in American history.”

Random Trivia: Actor Billy West based the voice of Futurama’s Zapp Brannigan in large part on Phil Hartman’s performance as Troy McClure.

Lionel Hutz is also known by the aliases Miguel Sanchez and Dr. Nguyen Van Falk.

5. Ned Flanders

Memorable Quote: “I’ve done everything the Bible says — even the stuff that contradicts the other stuff!”

Random Trivia: Ned’s habit of inserting nonsensical phrases like “diddly” and “doodly” into his sentences is the result of psychological conditioning to suppress his childhood rage.

4. Sideshow Bob

Memorable Quote: “Attempted murder? Now honestly, what is that? Do they give a Nobel Prize for attempted chemistry?”

Random Trivia: Sideshow Bob has a tattoo reading “Die Bart Die,” which he once helpfully explained to the Springfield parole board is German for “The Bart, The.”

3. Comic Book Guy

Memorable Quote: “Inspired by the most logical race in the galaxy, the Vulcans, breeding will be permitted once every seven years. For many of you, this will mean much less breeding; for me, much much more.”

Random Trivia: Comic Book Guy’s actual name as Jeff Albertson, a name purposefully chosen by the producers to upset fans hoping for something less generic.

2. Ralph Wiggum

Memorable Quote: “Me fail English? That’s unpossible!”

Random Trivia: The Bloodhound Gang “Ralph Wiggum” in 2005, a song with lyrics comprised almost entirely of quotes from the character.

1. Mr. Burns

Memorable Quote: “Listen, Spielbergo, Schindler and I are like peas in a pod. We’re both factory owners, we both made shells for the Nazis, but mine worked, dammit! Now go out there and win me that festival!”

Random Trivia: Mr. Burns’ Social Security Number is 000-00-0002 (he remains bitter at Franklin D. Roosevelt for snatching up 000-00-0001).