Humor writing: An introduction to writing more funnier word sentences

And we’re back! This post is going to be a more useful, less goofball update to my original humor writing post from 10 years ago(!), called “How to write funny shit for your blog.”

Humor writing lair
My humor writing lair, circa 2010.

What makes me qualified to talk about humor writing in an authoritative manner? Pardon the humble-brag, but I was one of the 1,275 applicants for The Onion’s 2020 fellowship and I never heard back from them, which in my experience is a sign that I stunned them stupid with my wit.

I’m accustomed to this. It happens frequently when I’m pitching travel editors, who are famously welcoming of goofball humor from freelancers they barely know.

Before we get to the useful tips, let’s take a moment to discuss the art of humor writing.

Lots of dirty liars are spreading dirty lies about how difficult humor writing is, so let’s address that first. Is it difficult to write funny? There are, not at all confusingly, four possible answers to that question.

  • Sometimes
  • Humor is subjective, so some humor writing styles are going to be more difficult than others
  • Humor is often about tone, which is trickier to establish in writing than in speech
  • Absofuckinglutely

I suppose the key takeaway is that humor is subjective. This is true in any context, but especially true in writing. Even the funniest sentence you write in your entire life is probably only going to entertain 75-80% of your readers.

The rest won’t get it or they’ll be offended or they’re just skimming and didn’t absorb the humor or they already dislike you for some other thing you wrote, but instead of ignoring you, for some reason they keep hate-reading you, and your attempts at being witty will just drive them into a stuttering rage.

And to answer the question zapping through your head right now, that previous sentence is extremely specific because I have an active imagination. No other reason.

Can humor be taught?

  • Usually. Theoretically you can teach someone anything, right? You can teach someone to ski off a cliff and not die, so why not humor?
  • Natural aptitude is nice and certainly helps a lot, but…
  • Aptitude or not, the most important thing is practice. Just like with any discipline, practice will make someone with no aptitude competent and it’ll make someone with a lot of aptitude wildly successful. Either way, practice is vital.

Humor writing: What’s funny?

Before you start trying to be funny, it’s important to understand exactly what is going to be funny and why. For the purposes of this introduction, I’ll explain four easy items in the humor writer’s handbook: Inside jokes, unexpected things, changing course and self-deprecation.

Inside jokes

People like to feel included and their personal opinions validated. If you need an example of that phenomenon, please refer to literally any religion.

Feeling like you’re part of a humongous, but private club makes the brain happy. So, when you share an anecdote that you know you and your audience have in common, they’re going to laugh, or at least feel good and smile, simply out of familiarity and/or sympathy. This is what I like to call “The Dane Cook Approach.”

Dane Cook does not tell jokes. (I’m using the present tense, because, though you may not have heard his name in a while, Cook is still performing.) There’s no set-up (in the traditional sense) and no punchline. He just tells stories that are familiar to his audience, with topics that a large number of people will relate to. The audience reaction is based more on their shared experience(s) with Cook, than the sheer weight of his wit.

I never personally preferred his comedic style, but the guy used to fill goddamn stadiums, so I’m just saying The Dane Cook Approach works fantastically well and we’ll leave it at that.

If you’re planning to rely heavily on inside jokes, before you write anything you need to establish who your audience is and what you have in common with them. Let’s say my audience is travelers. What do I, a well-traveled person, have in common with other travelers? Well, for starters, a bottomless well of unpleasant travel experiences.

Whether or not we have the same travel styles, unpleasant travel experiences are the great equalizer. These include airport hijinks, gastrointestinal liveliness, encounters with scam artists, wild animals behaving badly, uncooperative weather and the entire state of Florida, to name just a few.

But this is 2021 and the vast majority of your readers are going to be casual visitors who found your blog via Google searches, not dedicated readers. While it’s important to entertain your base (repeat visitors, social media followers, etc), you don’t want to totally alienate the people who are visiting your blog for the first time. If your wit is too obscure, too industry-specific, in poor taste, or just poorly executed attempts at wit, the only part of your blog stats that’ll grow will be your visitor bounce rate.

A quick aside: “In poor taste” is also subjective, obviously, but usually you know it when you see it. A common sign that you’re about to encounter humor of questionable taste is if someone describes their humor as “edgy” and then launches into 20 minutes of whining about people being too “woke.”

Unexpected things

A guy getting kicked in the produce section is, trust me, always unexpected. And it’s never not funny. In fact, it’s so reliably funny that we’re now seeing women getting kicked in the fish taco more frequently in TV and movies.

Not only does a blow to the groin work well as an unexpected moment, but it also satisfies the inside joke factor. Every guy has taken a blow to the produce section and knows how awful it is, so they laugh because they’re in on the joke. They’re part of the Blow to the Groin Club, which is a super reliable audience, because it includes almost half of all humanity. Women laugh at these moments too, but they don’t really know. I mean, they know, but they don’t know, you know?

The same goes, in reverse, for pregnancy jokes. Even though we’ll never really know how much pregnancy and giving birth sucks, us guys will laugh, because we’ve absorbed enough second-hand information to at least understand why it’s funny. But we also laugh because giving birth is gross (also, a little traumatizing) and gross-out comedy works extremely well in moderation. (See below.)

Another thing that’s unexpected is referring to a guy’s genitals as “the produce section.” And frankly, this is one of those bountiful, endlessly rich topics where pretty much any metaphor will get a laugh. Produce section, apple orchard, ball pit, locker room, trophy case… In the right context even the weirdest, nonsensical analogies will work. Stamp collection. This is what we call the “cheap laugh.” You usually only get one of those per blog post, so use them sparingly.

Changing course, A.K.A. the “lead away”

When you’re listening to someone speak, the human brain naturally tries to race the speaker (or writer) to the end of their thought. This allows you to screw with people by taking that thought to another place at the last second.

As the name suggests, changing course is most effectively used when it appears at or near the end of a sentence. If you change course at the beginning it doesn’t make any sense, since there was never a course to start with.

However, briefly changing course in the middle of a sentence can be an effective tool when you need the end of your thought to be an idea you’re trying to drive home. Let’s say you’re discussing something that’s an inherent bummer, like the importance of end-of-life planning, and you don’t want to loose the room (or the reader) to a wave of depression while trying to make your point.

To keep it (somewhat) light, you might say “When my mom died, I discovered to my horror that she’d made no end-of-life plans and her record-keeping was a disaster. I cried for the first week, ate 42 frozen pizzas over the next three weeks, then I arranged my own end-of-life plan, so my kids wouldn’t have to go through the same thing.” You’ve made your point without everyone dwelling on the universal bummer of losing one’s mom.

All that said, changing course at the end of a sentence will almost always be the most effective delivery. If you have a good gag, but for whatever reason it appears in the middle of a sentence, assuming it doesn’t turn the sentence into nonsense, rephrase it so it appears at or near the end.

I use this a lot. For example “I set a new record on the mechanical bull. Three broken ribs.” Or “The bus attendant handed out packs of peanuts. This is the perfect snack for small, crowded spaces, because peanuts are high in protein, they’re not messy, and they make me fart.”

If this is starting to sound too formulaic or contrived, welcome to humor writing! It’s a lot less organic than most people realize. Indeed, if the humor seems off-the-cuff or effortless, it’s usually a sign the writer/speaker put in a lot of work on that material. After lots of practice, changing course starts to feel like a pseudo-spontaneous process, like the muscle memory of shooting free throws, but it’s based on a killjoy formula that you intentionally or even unintentionally honed.

Self deprecation

If you want a treaties in self-deprecation, just watch like five Woody Allen films. He’s the king, and I’m sure someday this quality will make him extremely popular in prison.

(See how I placed “prison” at the end of that sentence for comedic effect? If I’d written “He’s the king, and if he ever ends up in prison he’ll be extremely popular,” the gag has less punch.)

Self deprecation is powerful on its own, but it’s especially powerful if your voice naturally leans to the confident or even egotistical side, because then when you switch suddenly to self-deprecation, you’re getting the added comedic effects of the unexpected thing and changing course.


“I love deadlines. I like the whooshing sound they make as they fly by.” – Douglas Adams (That one could go either way. It could be self-deprecation or “nobody tells me what to do, LOL!” arrogance.)

“Someone asked if I knew a good plastic surgeon. Would I look like this if I did?”

“Do you know that feeling when you meet someone and you both just fall madly in love? Yeah, me neither.”

Bonus humor writing handbook items: Shock value and/or the gross out

This works, partly because it falls under the “unexpected things” category and partly because humans just mysteriously love shocking and disgusting things.

Here’s one of my all time favorite examples of shock value:

“You can start a story with a quote twice in your career. Once when you’re an intern, and again if the Pope ever says fuck.” – @OHNewsroom

Normally I’d say it’s lazy to rely on curse words for wit, and cursing for laughs rapidly loses its effectiveness if you lean on it too much, but in this case the set-up made it OK.

On the other hand, remember “Go the F**k to Sleep,? read by Samuel L. Jackson? Remember how it was hilarious at the beginning, was still kinda funny in the middle and by the end you were like “Is this almost over?” This is Samuel L. Fucking Jackson we’re talking about here, a true artist with curse words, and even he can’t overcome the plummeting half life of curse word overuse.

With that abbreviated introduction to the theory of humor writing out of the way, here are four easy tools that anyone can use to punch up their writing.

Humor writing: Rule of three

This classic is pretty straightforward. Using the unexpected thing and changing course concepts above, you make a list of three things, with the third being the punchline. Occasionally you can stretch it to four items or even more, but two items isn’t enough to lay the groundwork for the course change.

Example: “Our attack dogs are named Bruno, Spike and Princess Fairy Rainbow.” See what I did? I set it up with “attack dogs,” then got the ball rolling with “Bruno” and “Spike,” commonly recognized names for attack dogs, but then instead of saying “Kujo” or “Donald Trump,” I changed course with the unexpected “Princess Fairy Rainbow.”

Princess Fairy Rainbow is a 180 degree course change, but even “Donald Trump” worked a little as a 90 degree course change. President Little Finger isn’t an attack dog, but he’s scary on pretty much every level, so it works.

More examples:

“The keys to sleeping soundly on an airplane are earplugs, an eye-shade and six shots of grain alcohol.”

“I live by three life rules: Stay out of debt, be kind to old ladies and savor every burp.”


I use exaggeration ALL of the time. Literally nonstop. Again, the unexpected thing is used at or near the end of a sentence, where they pack the most punch. Examples:

“The only way to get a cheap hotel room in Tokyo is to punch a cop in the throat.”

“The baby had a scream loud enough to explode a human eyeball.”

“Trump is so dumb that the Society for Dumb People named their library after him.” And you can keep the gag going if you like with something like “Appropriately, The Trump Library is a closet with a stack of second-hand Playboys on the floor.”


A callback, in terms of comedy, is a joke which refers to a joke (or even just an observation) told earlier in the set. The second joke is often presented in a different context than the initial joke. If you’ve watched a lot of stand up comedy shows, you may have noticed that callbacks are usually used at or near the end of the comedian’s set, so as to go out with the biggest laugh.

A great example of a callback at the end of a set is Ali’s Wong’s closer for her comedy special “Baby Cobra.” Somewhere in the middle of her act, she explains how she met her husband, found him attractive and learned he’d attended Harvard Business School, so she decided to “trap” him. At the end of her set, she works in this wonderful callback.

This works equally as well in written humor. The main principle behind the callback is to make the reader feel a sense of familiarity and inclusion with the subject matter, while simultaneously creating a rapport with your readers. When the second joke is told, it induces a feeling similar to that of being told a private or inside joke.

Can you find at least two callbacks in this piece?


All you’re doing here is describing something unfamiliar by comparing it with something absurd, while retaining at least a little accuracy. If you try to go without that shred of reality, you’ll only confuse your readers.

Examples with a hint of accuracy:

  • He’s hung like a sperm whale.
  • Ugly as a monkey’s butt.
  • His breath was worse than a beer fart.

Examples so weird, they’re confusing:

  • This curry is hotter than raisins.
  • I stubbed my toe so hard I saw hula-hoops.
  • That movie was so good it made my appendix explode.

Humor writing: words of warning

Don’t kill your readers with humor. You don’t need a gag in every sentence or even in every paragraph.

Twice a page (or every 250 words) is probably going to be plenty. Depending on the context, that might actually still be too much. Respect the topic and, again, know your audience.

Don’t be too clever

Again, readers likes to feel included, so don’t meander too far from humor material that they’ll identify with and/or understand. A brilliant sports analogy will likely fall flat with quilting enthusiasts. If you make a botany reference, no matter how ingenious, you’re probably going to baffle 97% of your readers.

Work the weirdness

“Best humor in stories isn’t in snark or one-liners, but in the absurdity of situations.” Spud Hilton

Travel is inherently weird. Comedian Tom Segura, who like Cook also mainly sticks to storytelling rather than standard jokes, knows how to work the weirdness. If you’re watching someone like Tom tell funny stories and thinking to yourself “Why don’t strange and hilarious things like that ever happen to me?” well there’s a good chance they actually have. You just have to figure out how to package and share those experiences in a humorous way.

If you pay close attention, most of the time Tom isn’t relying on a blow-by-blow account for the comedy when he tells a story. He often relies on his internal monologue which, as long as you don’t push the suspension of disbelief with overblown absurdity, can make a story about how you rented a scooter in Greece one time as funny as you want it to be.

“I felt liberated on this scooter, like anything was possible. The world was my oyster and my options limitless, as long as my options didn’t require me to leave Mykonos or move faster than 27 MPH, downhill.”

Tips to get people to read instead of skim

People skim. We’re bombarded with content every waking moment these days. There’s probably a shocking statistic to support this, but it’s safe to say that adults are currently consuming (or trying to consume) far more information per day than in any other period in humanity. It’s impossible to absorb it all, so keeping a reader engaged for even seven minutes is a small miracle.

But there are little tricks for snapping skimmers to attention. Don’t abuse these tricks or you’ll annoy your reader, but one or two overt attention-getters per post is fine.

An OG social media tactic for getting people’s eyes to un-glaze is to start a sentence/tweet with an unusual word.

Dirigible, for example.

(If I didn’t add these italics explaining it, I promise you that a skimming reader would stop cold at “Dirigible, for example,” go back and read the previous paragraph to find out WTF I’m referring to. Maybe even the previous two paragraphs.)

Coincidentally, a short, one sentence paragraph also catches the eye.

When used sparingly.

Humor writing: It’s OK to be unfunny – at first

It’s OK and even encouraged to write junk. You don’t get a segment on “Antiques Roadshow” without sifting through a giant, worthless, unfunny pile of junk.

The first draft of the joke/story is going to suck 99% of the time. Like stand-up comedy, sometimes the best iteration of the joke isn’t found until the fourth, fifth or twenty-fifth version. Give yourself permission to be unfunny. Write everything down, no matter how unfunny, and circle back to massage the humor later.

I cannot stress this enough: Write down ALL of your ideas as you get them. There’s a reason that stand-up comics all walk around with a notepad and pen or have volumes of notes in their phones. Like them, you should write down every idea, even idea fragments, because you won’t remember them later.

Finally, let’s briefly touch on voice in humor writing

The precarious art of printed humor can be less treacherous if you can rely on character and/or voice to help deliver the humor. If you can write with a voice that connects with your reader in a cornerstone post, it’ll allow you to stretch and flex your muscles as the snarky writer, or the goofy writer, or the dark humor writer from that point on.

Establishing voice is a crucial building block to unleashing your brand of funny in print, without worrying about the ubiquitous danger of your writing tone being misinterpreted. Then, after that’s been established, you can have a little fun with occasionally reversing that character. But that’s for the advanced humor writing class.