“Kids, you tried your best and you failed miserably. The lesson is: never try.” – Homer. I use this quote any time I or someone around me fails at something. Original context: This quote is from “Burns’ Heir” when neither Bart or Lisa were chosen as Burns’ heir. Example: “I can’t believe I just got last place in the 100-meter dash.” “The lesson is: never try.”

“Money can be exchanged for goods and services.” – Homer’s Brain. I say this quote every time I go shopping. Original context: Homer wants peanuts but instead finds a twenty dollar bill. His brain explains a simple form of how the economy works.

“I bet I’ll get blamed for this.” – Mayor Quimby. Original context: After Mayor Quimby makes jokes about the French’s resemblance to frogs, they launch a nuclear warhead at Springfield. Seeing the warhead go by his office window, Quimby says this line. Example: I would say this line if I am obviously at fault for something such as knocking an expensive vase onto the floor or deleting the computer’s hard drive.

10. Jasper Beardley. First appearance “Bart the General.” Grampa’s bearded friend from the Retirement Castle. Notable accomplishments: stealing Matlock’s pills, substitute-teaching the second grade at Springfield Elementary (and getting his beard caught in the pencil sharpener), avoiding the war draft by dressing as a woman, being shot in his wooden leg by Smithers, and freezing himself in the Kwik-E-Mart ice cream freezer in order to one day see the future. A favorite quote: “Hey, the drive thru’s for driving, not for parking.”

9. Troy McClure. First appearance “Homer vs. Lisa and the 8th Commandment.” Hi, he’s Troy McClure you might remember him from such cheesy TV specials, educational film strips and movies as “Man vs. Nature, Road to Victory,” “Mommy, What’s Wrong with that Man’s Face?” “Leper in the Backfield,” “Five Fabulous Weeks of the Chevy Chase Show,” and “The Contrabulous Fabtraption of Professor Horatio Hufnagel.” He’s Springfield’s resident washed-up movie star! A favorite quote: “If you ask me they’re all winners!… we’ll be cutting our first 40 contestants right after this.”

8. Fat Tony. First appearance “Bart the Murderer.” Fat Tony is one of those classic underrated characters that we take for granted because it seems like he’s always been there, but after 20 years of the Simpsons, few things delight me more than to see the Springfield Mafia at work, like in such classic moments as running every food vendor out of town (“The Twisted World of Marge Simpson”), serving rat milk to Springfield Elementary students (“Mayored to the Mob”), and giving Principal Skinner a good talking to (“Bart the Murderer”).

7. Ralph. First appearance “Moaning Lisa.” Ralph is a great character if used correctly. He must be completely random (“My cat’s name is mittens”). He must have that blissful innocence that we love (“My worm went in my mouth and I ate it”). He must have that little glint in his eyes that makes us think he might just be a secret genius (“I’m Ralph Wiggum, and I’ve been a good boy!”). A favorite quote: “What’s a diorama?” [Seconds before winning a diorama contest.]

6. Milhouse. First appearance “Simpsons Roasting on an Open Fire.” Milhouse has evolved very much over the series and each step on his evolutionary scale is as hilarious as the last. He starts out as Bart’s equally rambunctious friend, and eventually moves on to being a nerd (and proud of it, sometimes). Lately, he’s just become a sidekick to Bart’s wacky schemes. Plus, you’ve got to love those eyebrows. A favorite quote: “…if you say you’re a vampire, you get a free small soda at the movies.”

5. Lionel Hutz. First appearance “Bart Gets Hit by a Car.” Also known as Miguel Sanchez. Admit it – you’d hire Lionel Hutz as your lawyer just to get a few good laughs, even though you’d undoubtedly lose the case. He is the attorney of “I Can’t Believe it’s a Law Firm,” located in Springfield Mall. A favorite quote: “These books behind me don’t just make the office look good; they’re filled with useful legal tidbits just like that!”

4. Hans Moleman. First appearance “Principal Charming.” Hans Moleman is the closest thing Springfield has to a zombie, seeing as how he has repeatedly died and keeps coming back only to be killed again. Also, he’s completely blind without his glasses which caused him to drive the birthplace of Edgar Allen Poe into a ditch. Speaking of driving, he once drove his Gremlin off the road, almost hitting a tree; it doesn’t hit a tree, but his car explodes anyway. A favorite quote: “Ow… my brains…”

3. Declan Desmond. First appearance “‘Scuse Me While I Miss the Sky.” Very few good characters have been introduced in the past fifteen years on the Simpsons; all the good quirky characters were introduced in the first five or six years (e. g. Bumblebee Man, Captain McCallister, Uter). But Declan Desmond is a great character – he’s voiced by a Rutle! – and he’s also a former Monty Python cast member (Eric Idle). I greatly enjoy any medium that involves a snooty British filmmaker.

2. Sideshow Bob. First appearance “The Telltale Head.” The sequence of events surrounding Sideshow Bob is funny every time. It starts with him getting out of jail somehow, and eventually he works his way into the Simpson home [maybe as a maid ("Cape Feare") or dating Marge's sister, Selma ("Black Widower")]. Then, Bob puts his evil plan to kill Bart into action [a simple stabbing ("Cape Feare") or an elaborate stunt involving a faked death ("Funeral for a Fiend")] Here’s an example of how much I love Sideshow Bob: over a year ago, when I read the spoiler for “Funeral for a Fiend” that Sideshow Bob had died, I had laid out the preliminary plans for a “We Miss You Bob” web page which would’ve been filled with angry notes to the producers about how crazy they were for killing off Bob…

1. Comic Book Guy. First appearance “Three Men and a Comic Book.” Comic Book Guy epitomizes every obsessive Simpsons fan. He is a giant (both figuratively and literally) nerd. You show me a nerd, and I’ll show you a bigger nerd: Comic Book Guy. At various points he has been in possession of: a Mary Worth telephone, Radioactive Man # 1, a photograph of Sean Connery signed by Roger Moore, and the Ultimate Pog – featuring Steve Allen.
“Worst. Top Ten Simpsons Characters List. Ever.”

5. Time and Punishment from Treehosue of Horror V. All those alternate realities are really funny every time. I don’t know what would be better – donuts falling from the sky or Ned Flanders being the ruler of the universe. “This is indeed a disturbing universe.” – Maggie.

4. House of Whacks from Treehouse of Horror XII. Although it was a little disturbing to see Homer missing the back of his head with his brain exposed, this was a pretty funny segment. Some jokes that stand out in my memory are Homer mistaking the water heater for the Ultrahouse and, when forced to live with Patty and Selma, the computer trying to kill itself. (Personally, I would’ve chosen the voice of Matthew Perry for my house instead of Pierce Brosnan.)

3. I’ve Grown a Costume on Your Face from Treehouse of Horror XVI. I found this segment rather fun just for seeing all the characters in their costumes – Chief Wiggum as the Subway Guy, Moleman as a Mole (but he wasn’t wearing a costume), and of course Apu-D2.

2. Bart Simpson’s Dracula from Treehouse of Horror IV. “They’re dogs! Playing poker! [Maniacal laugh.]” This is probably the funniest, if not necessarily the scariest or best, Treehouse of Horror segment. Some of the funniest moments include the Super Fun Happy Slide and the cop-out ending parodying a Charlie Brown Christmas.

1. The Shinning from Treehouse of Horror V. Very few things in the world can make me happy no matter how unhappy I am. Two of those things are the Numa Numa kid, and seeing Homer make maniacal funny faces when Marge says, “… go crazy.”