How to Write a Humor Piece From a Headline
There are many ways to write a short humor piece.
You could crack open a blank Word document, or a blank journal, and start furiously writing random funny ideas as a stream of consciousness. You could also start by thinking of a real experience you once had near the dumpsters of a rural Dairy Queen, and start recounting that experience.
Those are nice methods, but I have a more efficient way to write a killer humor piece: Start with a headline.
A headline is the title of your humor piece. It’s the first thing your reader sees when encountering the piece. The headline is what attracts readers to your humor in the first place.
Examples help. Here are some humor headlines I like. These are all short pieces from the humor publication I edit, Slackjaw:
Ernest Hemingway At The Taco Bell Cantina by Jude Flannelly
Nicknames Of Vegan Mobsters by Sianna Lani
I’m Sorry Your Nana ‘Dyed’ In A ‘Comma’—Feedback On Your Grade 6 Creative Writing Essay by Colleen Landry
Replies To Yelp Reviews Of My Hedge Maze by Pat Landers
Coffee Is The Very Best Thing You Can Consume For Your Health And It Will Also Instantly Kill You by Molly Henderson
How to Convince Your Friend that Feet Exist by Murad Awan
New — It’s Adjunct Barbie™! by Katie Burgess
I Married Charles Darwin And He Immediately Stopped Evolving by Becky Veduccio Langton
The Sound Of Music But It Becomes Increasingly Obvious Rolf Is High On Speed by Julian Perez
This Song Sucks Ass: A Line By Line Analysis Of “Take Me Out To The Ball Game” And How I’d Fix It by Ryan Ciecwisz
Real quick: If you like the idea of writing a humor piece with a funny headline, sign up for the free humor workshop I’m teaching with Chill Subs and Write Or Die!
Okay, now let’s explore writing a funny piece from a headline, starting with the ‘Why.’
1. Why write a humor piece from a headline?
Starting with a funny headline ensures you have a clear, funny idea. That’s the strongest and simplest reason to write your humor headline before you write your humor piece.
But the headline is also what captures readers in the first place. By starting with the headline, you vet ideas that might actually get readers. Readers are good! If you are one of those writers who insist on writing “only for you,” by all means enjoy your solitude and your emo lifestyle. However, I think it’s lovely to get your work read. Humor writing that is only funny to you is especially troubling: it’s probably more self-indulgent than it is funny.
Third and finally, the headline-first method is supremely efficient: I prefer to spend my precious time drafting punchy, compelling ideas. I don’t want to waste time on a weak comedy premise.
I recommend starting the humor writing process by brainstorming a list of headlines — nothing more! Each headline should do two things:
(a) It should be funny or interesting. It should make your reader want to click.
(b) It should reveal a single, obvious comedic premise. In reading your headline, your reader should have a clear idea of what your piece is about and why reading it would be an enjoyable use of time.
My only personal exception to the headline-first approach is when I come up with a humor idea from a “morning pages” type free-writing exercise. But typically, I start with a list of headlines!
We’ll get to drafting the actual piece in a minute, but first, let’s look at some signs of a good headline.
2. How do you know if your humor headline is any good?
Here are three signs that you’ve got a winning humor headline:
The headline actually makes you laugh. Or, you pitch the headline to a friend, or your writing group, and they like it.
The headline excites you. You think it would be fun to write.
When you attempt to draft the headline, it immediately generates a bunch of ideas, jokes, beats, and so on. You have the feeling that this headline will be not too painful to spin into a first draft.
In my own process, the headlines that feel most exciting to me get priority. If an idea feels so exciting that I can’t wait to write it, I trust that feeling, and I write it.
If I have a headline where it feels hard to actually generate jokes from the premise, I don’t necessarily kill the idea, but I rank it lower on my list. I put it on the back burner.
I do also pitch many headlines to my writing group, and all else being equal, I give the ideas that my peers enjoy higher priority. However, if I truly love a specific idea, I don’t look for permission, I just write it.
Keep in mind the greater purpose of headline lists: to give yourself many options. If you choose a specific headline, but you have trouble drafting it, by all means, just pick another headline! Your headline options are infinite, so there is no need to suffer a humor headline that leads nowhere.
(Real quick: grab my Humor Writing Cheat Sheet to get a PDF of some of my best humor and satire writing tips and recommended resources.)
3. Humor headline pitfalls
Let me mention a few pitfalls to avoid when you create your headline list. These are the four most common headline mistakes I see as an editor.
The headline is not funny or interesting. Remember that you are writing a humor piece, and the best way to attract readers is with a headline that clearly communicates what is funny or interesting about your piece. Because this is not a depressing literary short story about how a river symbolizes alcoholism, you should not name your piece, “The River.” Your headline need not be laugh-out-loud funny (though it helps if it is), but it should at least be interesting.
The headline contains more than one comedic idea. The goal of your piece should be to escalate a single comedic idea, so make sure your headline has one main funny idea, not two or three or ten.
The headline is too clunky, elaborate, or awkward. It is more common for writers to produce clunky, confusing, or overly elaborate headlines than simplistic ones. As you explore headline ideas, veer towards simplicity, especially as you build your headline-writing chops.
The headline is cryptic, or it contains a highly niche reference that only you understand. You do not need to write your humor piece for the world as a whole. But having some relevance or appeal, to some group of readers, is a good thing. It’s fine if your piece is about fishing or tango dancing, and your piece is mainly funny to anglers or dancers, just trying to aim for a real audience of more than just you.
In short, shoot for funny, concise, clear headlines that communicate a single comedic idea. Now let’s get to writing!
4. How to write a humor piece in a single weekend
To start, brainstorm a list of five to ten funny headlines. Don’t think too hard about each headline. Getting several ideas down on paper is more important than trying to divine one “perfect” headline.
Why is quantity superior here? Two reasons. First, I can tell you from experience that generating a large quantity of headline ideas is simply a more efficient and effective way to find a single good headline. Empirically, it beats toiling forever on one headline. You may have heard the parable of the pottery or photography classes that got a better result with iteration and quantity. Similar idea here.
Second, the act of writing many headline ideas will help put you in a flow state where your judgment lowers and you trust your intuition more. This kind of flow state is so helpful for finding weird and wonderful humor premise ideas. When you’re writing many headlines, any given headline is not so important to your outcome, so you can afford to take more risks and try a comedic idea that your judgey editor brain might otherwise criticize into oblivion. Quantity allows you to tap into your inner clown-god.
Now that you’ve got a headline list, simply pick your favorite headline. If you like, you can let the headline list sit for a day or two, then pick your favorite with fresh eyes.
Alternately, run your headline list by a friend or two, or run it by your writing group. Ask them which headline(s), from the list, they enjoy the most.
Once you’ve selected your winning headline, pat your back three to five times. Not six though, that’s too many pats. With a solid premise in hand, much of your work is already done. Your next task is to expand the headline idea into a full draft.
5. The humor drafting process: a lightly structured approach
I recommend a draft of 300 - 800 words for a humor piece. Some short humor pieces are shorter or longer than that, but I’ve found that 300 - 800 is the sweet spot. That’s just enough words to explore your premise and escalate it to hilarity.
Premise-driven pieces typically lose steam starting around 1,000 words. If you have a humorous piece over 1,000 words, that will typically be a humorous short story or a personal essay. It will have a narrative that can be explored indefinitely. But when you are writing a premise-driven piece from a headline, I recommend shooting for fewer than 1,000 words.
A word on format. A humor piece can use any format. Here are some common ones: a monologue or speech, a list or listicle, a personal essay, a traditional short fiction piece, a letter or email, or a screenplay or literary dialogue. Check out the formats of the pieces linked at the start of this essay. For even more format ideas, I’ve got some ideas in this blog post.
Alright, now you’re ready to write. There’s no “correct” way to draft a humor piece, but here’s a simple four-step process that could serve you well:
First, just generate as many raw ideas, jokes, humorous riffs, and funny sentences as possible, using the headline. Don’t worry about structure. Don’t worry about overall coherence. Allow for organic discovery as you riff on the headline. Follow your instincts of what’s funniest, weirdest, and most joyful to you. Overall, just focus on getting funny ideas down with one restriction: every idea should be an exploration of the humorous headline you selected. This is the only restriction. Stay laser-focused on the premise!
Put your funny ideas into coherent paragraphs, and edit the paragraphs into a first draft. You can also think of each paragraph as a comedic “beat” and the entire piece as an escalating series of beats.
Edit your piece into the leanest, meanest, tightest, and funniest piece of writing you can. Again, make sure everything in the piece is 100% on-premise and is an escalation of the precise headline you chose. You can also review these ten common humor-writing mistakes.
Optional: Send your draft to a writing buddy or writing group for review. After you get comments, go back to step (c), the editing phase, and repeat this as many times as necessary.
Again, that’s just one way to structure your humor writing process. Feel free to use that or ignore it.
But if you do all of that, you’ve written a short humor piece. Great. I’m thrilled! Now write more headlines and do it again.
And that’s that. Any other advice? Sure: Be smart. Be silly. Be bold. And remember to have a lot of fun!
Finally, please join me for a free 60-minute workshop on humor writing, sponsored by Chill Subs and Write or Die.
Not only will we look more deeply at the humor writing process, but there will be time for questions, and you can ask me anything you’d like about humor writing. As a further bonus, some brave souls can pitch their headlines live during the workshop, and we’ll discuss these headline pitches. This will give you an even deeper look at the headline-writing process.
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Find all of my favorite humor writing resources here.