The 20 best 'Simpsons' gags (Part 1)

Next month will mark the 20th season of The Simpsons, and to celebrate the historic mark I embarked a month ago on ranking its 20 best gags. Arriving at 20 was not easy, and deciding on a final ranking of the 20 meant many tough choices. In weeding out the hundreds of elite gags from The Simpsons, I settled on a fairly basic criterion: the gags had to be a great representation of Simpsons' trademark humor, which is so often imitated, and also staying power -- able to make you laugh years later after you've heard it countless times.

What I found after arriving at the top 20 was that not every popular character was represented (no Troy McClure, no Willy, no Ralph), and that many of the consensus top episodes also did not make the cut (my three favorite episodes fall into this category). So no bias was given to characters and episodes, but I can't say the same for the seasons that are represented. Try as I did, I just couldn't find any worthy gags from the last several seasons to put on the list, not to say there weren't contenders. This could be due to the high level of gags from The Simpsons' golden age in seasons 3-6, when the show was writing its own standards of humor, before trying to live up to those standards in later seasons. On this list you'll find some well-known gags, a few you might have forgotten about, and a handful of underrated gems. Some of the entries have accompanying video clips, via Fox's Hulu.com (Simpsons clips on YouTube usually vanish after a couple days).

Today also marks the third anniversary of DVD Panache. My first post was about The Simpsons, it wasn't very good, but it was a beginning. And now here I am three years later with The Simpsons again. Enjoy the list:

20. 100 Tacos

The Episode: Bart the Fink (Season 7)
The Setup: After the passing of their Great Aunt Hortense, the Simpsons family gains a modest inheritance of $100 each.
The Joke:

MARGE: What are you going to do with your money, kids?
BART: There's a special down at the Taco Mat: 100 tacos for $100. I'm going to get that.
(Later, as Bart spies the Taco Mat)
COMIC BOOK GUY: (wheeling out 100 tacos) This should provide adequate sustenance for the Dr. Who marathon!

Notes: One of the most vicious of all the Comic Book Guy jokes, I love the idea of 100 tacos for $100 being a "special" at Taco Mat, since tacos cost about $1 in most parts of the world. According to the The Simpsons Guide to Springfield, this deal offers the consumer $5 in savings.

19. Earl Warren, stripper?

The Episode: Itchy & Scratchy: The Movie (Season 4)
The Setup: As Bart is once again destroying the Simpsons residence, Marge comes home to see Homer oblivious to the situation.
The Joke:

MARGE: Do you want your son to become Chief Justice of the Supreme Court, or a sleazy male stripper?
HOMER: Can't he be both, like the late Earl Warren?
MARGE: Earl Warren was not a stripper.
HOMER: Marge, now who's being naive?

Notes: The genius of this joke lies in the subtle build-up. In this episode we learn of Homer's strangely impressive knowledge of the Supreme Court, which adds another layer to his ridiculous Earl Warren comment. When hearing that Bart could turn his poor grades around and earn a spot on the highest court, he easily lists his favorite justices, and later mentions Justice Suiter. The care given to setting up this short joke is something you rarely see on television.

18. Steamed Hams

The Episode: 22 Short Films About Springfield (Season 7)
The Setup: Preparing for a nerve-wracking dinner with Superintendent Chalmers, Principal Skinner is horrified to see his roast go up in smoke. When Chalmers inquires about the smoke, Skinner assures him that it is in fact steam, from the steamed clams he was making. With a burnt roast in the oven, Skinner rushes to Krusty Burger for a dinner that is definitely not steamed clams.
The Joke:

SKINNER: Superintendent, I hope you're ready for mouth-watering hamburgers.
CHALMERS: I thought we were having steamed clams.
SKINNER: Oh, no, I said "steamed hams." That's what I call hamburgers.
CHALMERS: You call hamburgers steamed hams.
SKINNER: It's a regional dialect.
CHALMERS: Uh-huh, what region?
SKINNER: Uh, upstate New York.
CHALMERS: Really. Well, I'm from Utica and I never heard anyone use the phrase "steamed hams."
SKINNER: Oh, not in Utica, no; it's an Albany expression.
CHALMER: I see.

Notes: The finest example of Skinner embarrassing himself in front of Chalmers as a result of his own good intentions. What makes this exchange so perfect is the delivery of Chalmers' final line -- it sounds like he's on the verge of believing Skinner's B.S. It's also hilarious how Chalmers reacts to the Skinner's initial "steamed hams" revelation, treating it somewhere between pathetic and amusing.

17. The Jazz Umbrella

The Episode: 'Round Springfield (Season 6)
The Setup: Bleeding Gums Murphy recalls his jazz mentor, Blind Willie Witherspoon.
The Joke:

WILLIE: I've been playing jazz for 30 years and just can't make a go of it. I want you to have my saxophone.
MURPHY: That's not a saxophone, it's an umbrella.
WILLIE: You mean I've been playing an umbrella for 30 years?
MURPHY: We all thought it was kinda funny.
WILLIE: That's not funny.

Notes: Another in a long list of jazz bashings from "Round Springfield," the Jazz Umbrella gag is one of the better flashbacks that permeated Season 6 (this joke device would be famously copied by Family Guy). Willie's final line could have only come from Simpsons writers.

16. Jeremy's Iron

The Episode: Lisa's Rival (Season 6)
The Setup: After meeting her intellectual rival, Alison, Lisa is invited over to the girl's house, where she meets her father.
The Joke:

TAYLOR: Hi Lisa, I'm Alison's father, Professor Taylor, I've heard great things about you.
LISA: Oh really, I--
TAYLOR: Oh, don't be modest. I'm glad we have someone who can join us in our anagram game.
ALISON: We take proper names and rearrange the letters to form a description of that person.
TAYLOR: Like, uh ... Alec Guinness.
ALISON: (thinks) ... Genuine class!
TAYLOR: Ho, ho, very good. All right Lisa, how about ... Jeremy Irons.
LISA: Umm, Jeremy's ... Iron?
TAYLOR: Well,... that is very good ... for a first try. You know what? I have a ball, perhaps you'd like to bounce it?

Notes: This gag's greatness is almost as unbelievable as Alison's anagram wizardry. The Simpsons has a long history of viciously skewering the over-educated (as you will see in this feature), and this gag is one of the best of that class. What I love about this exchange are Taylor's choices in the game, picking out Guinness and Irons off the top of his head. Since he's a stuffy professor, the first names he can think of are celebrated British actors.

15. Naked Lunch Date

The Episode: Bart on the Road (Season 7)
The Setup: After securing a fake I.D., Bart and friends embark on a journey of adult-oriented activities, and their first stop is a movie clearly not suitable for children. But as Nelson points out as they exit the theater, the David Cronenberg movie is guilty of a little false advertising.
The Joke:

NELSON: "I can think of at least two things wrong with that title."

Notes: The premise of going to see an inappropriate movie is overflowing with potential, and the result is miles from predictable. For anyone familiar with Cronenberg's movie, or William S. Burrough's novel, this joke reaches milk-out-your-nose funny: Naked Lunch features talking typewriters, lots of bugs and women getting shot in the head ... but sadly no women of the naked variety. Jokes like this one helped The Simpsons transcend its animated family show medium, as clearly this was aimed far above the heads of kids dancing The Bartman, or even their older siblings.

14. Krusty's Koffee

The Episode: Radioactive Man (Season 7)
The Setup: With Hollywood in town to film the much-anticipated Radioactive Man movie, Springfield rolls out the red carpet. Some local talent will be utilized, and surely that includes famed actor Krusty, right? Unfortunately, the role of Crispy the Clown has already been filled, and Krusty is forced to beg for a bit part. When the movie's hugely expensive centerpiece stunt goes down in acid ("real acid"), the production looks doomed, and there are also more pressing concerns ...
The Joke:

KRUSTY: "I want to talk about this coffee!"

Notes: This is an underrated gem that over the years has become one of my favorites, from one of the series' all-time best episodes. The build-up to this joke is similar to No. 19, with the seed planted much earlier, except this one has a greater payoff. In seeing Krusty in full "Dr. Clownius" costume, we learn that Krusty somehow secured a role in the film, and has taken his trademark wannabe-Hollywood abrasiveness ... well, Hollywood.

13. Two Ruined Jackets

The Episode: Secrets of a Successful Marriage (Season 5)
The Setup: In order to gain respect, and silence complaints that he's mentally slow, Homer offers his marital expertise as an instructor of an adult education course.
The Joke:

HOMER: Look everyone, now that I'm a teacher I've sewn patches on my elbows!
MARGE: Homer, that's supposed to be leather patches on a tweed jacket, not the other way around. You've ruined a perfectly good jacket.
HOMER: Ah, incorrect Marge -- two perfectly good jackets! (Homer holds up tweed jacket where the patches were cut).

Notes: Homer's understanding of academia includes the fact that he is now able to correct his peers in a scholarly manner. It should have been a given that as a teacher, Homer would utilize a pipe, but it still adds another awesome layer to this joke.

12. Meet Cerberus

The Episode: The Itchy & Scratchy & Poochie Show (Season 8)
The Setup: With ratings sagging, The Itchy & Scratchy Show needs revamping -- namely, a new character. In a meeting with Krusty and the show's writers, a savvy marketing executive spells out exactly what she has in mind.
The Joke:

KRUSTY: Whaddaya got in mind, a sexy broad, a gangster octopus?
MEYERS: No, no, no. The animal chain of command goes mouse, cat, dog. (To writers) D-O-G.
WEINSTEIN: Uh, a dog? Isn't that a tad predictable?
LADY: In your dreams. We're talking about the original dog from hell!
OAKLEY: You mean Cerberus?

Notes: An offshoot of The Simpsons' self-deprecating humor was the show's lampooning of its own writers, portraying them as Ivy League shut-ins (with at least half of that statement being true). The underlying gag is that a show like Itchy & Scratchy would need a team of writers at all.

11. Stringent Usury LawsEpisode: Lisa's Pony (Season 3)

The Setup: Desperate to regain Lisa's affection, Homer decides to finally buy her a pony -- which don't come cheap. Homer has no choice but to ask for a loan from his employee credit union, where he meets a familiar face.
The Joke:

HOMER: Mr. Burns, you do this personally?
BURNS: Oh it's a hobby, I don't do this for any personal gain, heavens no. By the way are you acquainted with our state's stringent usury laws?
HOMER: Usury..?
BURNS: Oh, silly me, I must have just made up a word that doesn't exist! Now, what is the purpose of this loan.
HOMER: I want to buy a pony...
BURNS: Isn't that cute! Smithers, he wants to join the horsey set. That is it, isn't it? You're not planning to eat it?
HOMER: No, no, I need to get it for my little girl because she doesn't love me any--
SMITHERS: Shut up Simpson. Do you have any collateral?
BURNS: Oh Smithers, don't be so cold -- his spirit is my collateral. Now just sign this form (laughing maniacally). Ahem, sorry, I was just laughing at something funny Smithers said today.
SMITHERS: I didn't say anything funny, sir.
BURNS: (under breath) Shut up!

Notes: I love this side of Mr. Burns, at once sarcastic, vindictive and playful. It's also apparent from his tone that Mr. Burns is just a little bit scared that Homer was asking for a $5,000 loan so he could purchase and slaughter a horse for his own insatiable appetite.

Tune in Monday for Part 2!