Writing jokes with The Simpsons

So it's come to this: a perfectly cromulent essay about what I've learned from one of the greatest comedy shows of all time.

I fell in love with comedy in the summer of ‘98.

It was a simpler time, when you could only watch the shows the TV gods wanted you to watch — and I guess they really wanted me to watch The Simpsons. Between BBC Two (one episode every weeknight at 6pm) and Sky One (two episodes every night at 7pm, with a bonus two on Fridays), you could watch up to 21 episodes a week.

I often watched every single one.

Within a couple of years, I was a super fan. Sure, I could quote lines, but that was the entry level.¹ My school friend and I used to play a game where we’d flick to a random page of the official guide, start reading the plot summary, and see how quickly we could name the episode. (The answer was usually: way too quickly.)

I’ve since lost that ability — partly because there are now over 750 episodes; partly because I realised I should probably go outside at some point. But the show will always be my first comedy love, and remains the gold standard to which I aspire.

And so, without further ado: here is a totally non-comprehensive list of my favourite gags from The Simpsons, and the insights we can apply to our own humble attempts.

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1. He said it was just a name!

For the benefit of anyone who might be new to comedy writing, let’s start with the basics. In general, a joke is comprised of two parts:²

1. The expectation: make it seem like you mean one thing.

2. The reversal: reveal that you actually mean something else.

For example: when I tell people I’m a comedy writer, the expectation is that I’m funny in real life. The reversal is that I just go into very dry detail about what a joke is. The same thing is happening with this classic Simpsons fantasy sequence:

• JUDGE: I sentence you to a lifetime of horror on Monster Island! (Whispering) Don’t worry, it’s just a name…

• Cut to: Lisa and some other guy being chased by a fire-breathing monster.

• LISA: He said it was just a name!!

• OTHER GUY: What he meant was that Monster Island is actually a peninsula.

Our expectation — and unfortunately Lisa’s — is that he’s referring to the ‘Monster’ part of ‘Monster Island’. The reversal is that he’s actually referring to ‘Island’.

But the true genius of The Simpsons is that almost anything can set an expectation — it doesn’t just have to be dialogue. For example: in cinematic language, a cross fade and a musical cue usually imply that a long time has passed. But you can reverse this too, like when Patty and Selma decide to tell everyone that Marge is pregnant…

✍️ Takeaway: set an expectation and find a surprising way to reverse it.

2. I told that idiot to slice my sandwich

Although The Simpsons has been written by dozens of writers, its comedic sensibility is often attributed to just one: George Meyer. The New Yorker even wrote a profile about him³ — and I often revisit that article when I need some inspiration, or if I want to feel good about myself as the kind of person who reads The New Yorker.

There’s a particularly great story about a joke from Realty Bites (S9 E9). Snake tries to steal a car back from Homer, and so “contrives a scheme worthy of Wile E. Coyote”: he stretches a piano wire across the road — from ACME, no less — in the hope of decapitating him as he drives by. Thankfully, Homer gets distracted by a gumball on the floor(!) — but unfortunately, there’s another car behind him:

“The driver of the second car is holding a sandwich at a ridiculous angle high up over his head and saying, ‘I told that idiot to slice my sandwich,’” [Mike] Scully explained. “That’s where we were going with the joke [– the wire would cut the sandwich]. But then George suddenly said, ‘What if the wire cuts off his arm?’”

I love that story because it’s a good reminder not to settle for your first idea. It’s like pulling on a rubber band: you want to see how far you can stretch the reversal without it snapping away from the expectation (even if it means losing an arm).

✍️ Takeaway: don’t settle for your first idea. (Plus: fellow writers can help!)

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3. No, no, I said ‘steamed hams’

Possibly the most well-known 2 minutes and 48 seconds from The Simpsons: Principal Skinner invites Superintendent Chalmers for dinner, and things go horribly, horribly wrong. There’s so much to love in this sequence, but the highlight is when Skinner realises that the kitchen is on fire, and decides to cover it up:

• CHALMERS: Good lord, what is happening in there?

• SKINNER: Aurora borealis.

• CHALMERS: Aurora borealis? At this time of year, at this time of day, in this part of the country, localised entirely within your kitchen!?

• SKINNER: … yes.

• CHALMERS: May I see it?

I cannot overstate how much I love it when a character does or says something truly ridiculous, and another character accepts it instead of shutting it down. (In a way, this is a basic version of the ‘yes, and…’ rule famous from improv.) Chalmers could’ve easily continued being the voice of reason — e.g. “Do you really think I’m going to fall for that?” — but it’s so much funnier that he believes him, if only for a split second.

See also: Mr. Burns enquiring about his cube, or the prevalence of the name ‘Bort’. 

✍️ Prompt: what if you accepted the ridiculousness instead of shutting it down?

4. I call it ‘Billy and the Clonosaurus’

That said, it’s also funny to shut things down.

• SKINNER: Now I finally have time to do what I’ve always wanted: write the great American novel. Mine is about a futuristic amusement park where dinosaurs are brought to life through advanced cloning techniques.

• Apu, behind the counter, looks unimpressed.

• SKINNER: I call it: ‘Billy and the Clonosaurus’!

• APU: Oh, you have got to be kidding sir. First you think of an idea that has already been done. And then you give it a title that nobody could possibly like. Didn’t you think this through? // It was on the bestseller list for eighteen months! Every magazine cover had it… // One of the most popular movies of all time, sir! What were you thinking!? (Beat) I mean… thank you, come again.

This is a great example of one of the tricks I learned doing stand-up: you can make things funnier by ramping up the emotion. A different sitcom might have Apu reply with a quick retort — “You mean Jurassic Park?” — but instead, we’re treated to a rant so deliciously long and disproportionate that it spans two whole time jumps.

And the emotion doesn’t always have to be anger — for example, I love the pure joy that spreads across Homer’s face when he realises that the dud looks like Milhouse.⁴

✍️ Prompt: what if you ramped up the emotion?

5. Sideshow Bob Walks Into A Rake

I don’t know why I’m even trying to put this into words, but here it goes: Sideshow Bob gets out from under a car, where he’s been hiding, and walks into a rake. And then again. And then again. And then another six times after that.

Here, the ‘reversal’ isn’t what a character says or does, but the unexpected number of times they say or do it. Chris Turner describes it best in his book Planet Simpson:

The first thwack, you might chuckle a bit at such a shopworn gag. Same goes for the second and third. By the fourth or fifth, you’re perhaps finding the gag a little tedious. By the seventh or eighth thwack, though, the humour of the scene re-emerges, amplified exponentially… it’s just hilarious.

This is such a criminally underused device: I don’t think I’ve seen it deployed in any other sitcom? But The Simpsons has two iconic examples of it — the other, of course, is when Homer is about to lose his dental plan, but remembers that Lisa needs braces…

6. Sideshow Bob Walks Into A Rake

I don’t know why I’m even trying to put this into words, but here it goes: Sideshow Bob gets out from under a car, where he’s been hiding, and walks into a rake. And then again. And then again. And then another six times after that.

Here, the ‘reversal’ isn’t what a character says or does, but the unexpected number of times they say or do it. Chris Turner describes it best in his book Planet Simpson:

The first thwack, you might chuckle a bit at such a shopworn gag. Same goes for the second and third. By the fourth or fifth, you’re perhaps finding the gag a little tedious. By the seventh or eighth thwack, though, the humour of the scene re-emerges, amplified exponentially… it’s just hilarious.

This is such a criminally underused device: I don’t think I’ve seen it deployed in any other sitcom? But The Simpsons has two iconic examples of it — the other, of course, is when Homer is about to lose his dental plan, but remembers that Lisa needs braces…

7. Oh, it’s a donkey!

I find it really hard to write jokes where characters are being ‘stupid’, because I don’t think they can just be wrong — it’s way more satisfying when they’re wrong in a clever way, and there’s some kind of twisted logic to their thoughts or actions.

For example: consider this brilliant throwaway gag from Natural Born Kissers (S9 E25).⁵ If you’re one of those hardcore jigsaw enthusiasts that like to do them without looking at the box — my wife is one and refers to doing so as ‘cheating’ — then you have to solve it before you know what the picture is supposed to be. That’s the moment that’s being captured here; a character places a piece, before triumphantly declaring:

• HOTEL GUEST: Oh, it’s a donkey!

But the twist is that it was obvious that it was a donkey several pieces ago.

And so, in literally the split second after the syllable ‘key’, your brain realises that: 1. she’s been sitting there all this time without recognising it, and 2: for some reason, she needed that last piece before she could do so. You’re forced to tune into that twisted logic, and once you do: welcome to Lolsville, population you.

Of course, Homer is the true master of this type of reasoning — such as his foolproof plan to save himself from sinking into a tar pit. 

✍️ Takeaway: being wrong is funnier if there’s a twisted logic to it.

8. I thought you said Troy McClure was dead?

As you can probably tell by now, I have a lot of reverence for The Simpsons — but I still don’t think I can convey just how much I’m in awe of this joke. It starts with Homer and Marge talking about the washed-up actor, Troy McClure:

• HOMER: Who’d have thought he’d turn out to be such a weirdo?

• MARGE: What are you talking about?

• HOMER: (whispering) You know, his bizarre personal life. The weird things they say he does down at the aquarium. Why, I heard —

Later in the episode, we see Troy visiting the DMV. But two of Springfield’s resident mobsters, Louie and Fat Tony, seem surprised to see him:

• LOUIE: Hey boss, I thought you said Troy McClure was dead?

• FAT TONY: No, what I said was: he sleeps with the fishes.

I know you can’t see me, but I’m making a *chef’s kiss* gesture right now.

Maybe it’s the way they stretched the set-up over multiple scenes. Maybe it’s the fact that they actually had two resident mobster characters who would naturally use such a phrase. Or maybe it’s the possibility that they might have constructed the entire plot of this episode just so they could do that joke. Either way, I think it’s a masterpiece.

✍️ Prompt: what if you… just wrote a joke that was that good? 

Bonus: there’s always a joke

Finally: whenever I’m stuck, I like to remind myself of writer Mike Reiss’ philosophy: there’s always a joke. He describes an example in his book Springfield Confidential⁶ — when they were trying to come up with a gag for Lisa the Beauty Queen (S4 E4).

The setup is that Lisa wins the Little Miss Springfield pageant, and decides to use her platform to become an outspoken activist. Unfortunately, this doesn’t sit well with the pageant officials — so they look through her entry form, which Homer submitted on her behalf, in the hope of finding a mistake that would disqualify her. But what?

We pitched longer on this joke than any I can remember. Some suggestions made Homer look too stupid, others too lazy; worst of all, none of them were funny…

By one in the morning, we were exhausted, frustrated, and ready to settle for a lame joke… or no joke at all. That’s when a writer named Frank spoke up. Frank wrote great scripts, but he rarely spoke — he was a Buddha-like man who would plop himself into a chair first thing every morning, shut his eyes, and go silent. He was either meditating, sleeping, or dead. In any case, we’d whisper around Frank all day, not wanting to disturb him. But on this particular session, just when we were about to give up, Frank opened his eyes and said: “In the space marked ‘Do not write in this box,’ Homer wrote ‘OK.’”

And so, we get to the most important takeaway of all: if you’re stuck, and nothing seems to be working, just keep going. There’s always a joke.

Except when I try to come up with an ending for this, apparently.

1. I forgot that I even learned to play the saxophone because of Lisa!

2. I recently read the excellent Be Funny or Die by

Joel Morris

, which generalises this further as: construct, confirm and confound. Highly recommend it if you want to dive deeper.

3. He was recently joined by John Swartzwelder, who got one of his own 21 years later.

4. Okay, so up until now I’ve been refraining from pointing out the wonderful animation and direction in The Simpsons, because I thought it’d be a distraction, but I can’t hold it in any longer. I love the quick cuts into Chalmers’ face when he’s dubious about aurora borealis. I love the split second of Apu looking angry while Skinner is describing his novel. And here, I love the animation of Homer’s smile when he realises what he’s found. Ah, that’s better.

5. It’s worth noting that this gag is squeezed into five seconds of scene setting before the core of the scene actually starts. How can any of us ever hope to compare!?

6. Thanks to Nathan Dean for originally sharing this with me!