Writing Humor When You Don’t Think You’re Funny

by Amy Ayres
published in Writing

[Author’s note: This is the first article in my new column series about humor writing called “What’s So Funny”. It addresses the so-called how-to’s, different approaches to humor writing, funny people who inspire me, and so on.]

Some people are intimidated by writing humor. They think they just aren’t funny enough. And while it isn’t necessarily easy and some think it can’t be taught, I think it’s a good exercise to at least try. It’s one of those things that gets better with practice. 

Writing humor is an exercise in creativity above all else. It’s an exercise in authenticity and it can ultimately be therapeutic. Even the funniest people in the world admit that they aren’t funny all the time. Or when they are being funny, it’s from a dark place. Or when they sit down to try to be funny they just…can’t.

Speaking of funny people, I compiled a short list of some who are known not only for writing humor, but also are considered giants in that area. I refer to their insights on creativity, writing from a personal place, what they think makes writing funny, and the ways they have struggled to just be funny. All that with some self-deprecation thrown in for good measure. You know, to make them seem more relatable.

David Sedaris

I’ve been taking Sedaris’ MasterClass, which is a good place to start when you want to learn how to “write funny.” Sedaris admits that he doesn’t try writing humor, he just journals and notes observations. Then later he relays a story he believes is funny and lets the story do all of the work. He loathes setups and punchlines and believes the humor lies in the bizarre.

He suggests that writing the story isn’t the hardest part. The difficulty is putting himself in “strange” situations where he knows funny things will happen and then letting them play out without intervening.

Sedaris admits to people-watching and eavesdropping to get most of his story ideas, once overhearing a couple speaking French accusing him of being a pickpocket. Famously, Sedaris did not intervene or explain that he was in fact Davis Sedaris and not a pickpocket because he “wanted to see what would happen next.”

David says he uses three main tools when trying to make an audience or reader laugh: quoting funny people, exaggeration, and self-deprecation.  

  1. In reference to quoting funny people: “When the people around you are funny, you can bring them into your work.” 
  2. When he exaggerates he practices “stretching a scenario into the most ridiculous version you can imagine.”
  3. And when you lovingly put yourself down: “Be harder on yourself than you are on anyone else in a story.”

Sedaris also highly recommends not just writing for yourself, but for an audience, and always trying to do something new. He says, “I never wanted to be the kind of writer who reads one thing that works and then drags it around.”

John Cleese (and Conan O’Brien)

If you are unfamiliar with John Cleese, he is best known as one of the founding members of Monty Python. According to Wikipedia: “The Pythons’ influence on comedy has been compared to the Beatles’ influence on music.” There are two ways to look at this kind of humor: it might be out-dated for some, timeless for others. Like all humor, it is a matter of taste.

Either way, Cleese has been writing comedy and about the act of writing comedy for almost five decades, so I thought it only fair to give him some airtime. 

He has very recently published a book about creativity called Creativity: A Short and Cheerful Guide. He was also interviewed by another comedy great, Conan O’Brien on his podcast Conan O’Brien Needs a Friend. In the interview, O’Brien and Cleese go back and forth on what they think makes for funny writing. 

O’Brien believes a lot of his funny writing comes from the unconscious. “I will hit my head against a wall for hours at a time with a legal pad in front of me…I don’t think I’m getting anywhere. Then I go to sleep and when I wake up I see things more clearly, and I have ideas that didn’t exist before.” He says that is essentially what Cleese’s book is about. 

Cleese says it’s “embarrassing that we are of the same mind.” But that ”when you put pressure on yourself to write something funny, you always go for what’s derivative.” 

O’Brien continues to say that “so much of writing is agonizing, wandering around, and procrastinating…making an excuse to buy a new desk… then suddenly the ideas come to you.” He also admits that much of his early writing was an imitation of Monty Python’s style, and that he thinks any good writer of comedy started out by copying someone else.

Both Cleese and O’Brien cite their odd and difficult upbringings for the reason they are so good at comedy.

Ultimately, they both agree that they too have a penchant for the bizarre, and when they let themselves improvise and play, the funny stuff comes out.

Samantha Irby

Author of many hilarious collections of essays: We Are Never Meeting in Real Life; Meaty; New Year, Same Trash, including her most recent (and my favorite) Wow, No Thank You. I can’t say enough good things about that book. It takes all of this writing advice and lights it on fire—not to burn it up, but to shoot it into orbit.

Irby knows that writing from personal wounds, including her struggles with childhood demons, body image, Crohn’s disease, degenerative arthritis, and depression, only gives her more material to work with.

In a recent interview with the Rumpus, called Laughing Through Life, she was asked about her journey from aspiring to sought-after humor writer. She also talks a bit about what inspires her humor and prompts her to write:

Rumpus: Humor can heal a lot. When did you first realize that humor could be a way to get through things that felt inexplicable in life?

Irby: I honestly don’t know. I had a terrible childhood and early adulthood but didn’t have money for therapy so I tried to laugh about things rather than crying over them. I’m sure there’s a therapist out there who’d probably say that my making jokes as a coping mechanism rather than unpacking my myriad issues with a licensed and trained professional is a terrible approach to life and is probably part of the reason I remain deeply depressed. But I’ve been good at it so far and now I’m afraid to stop! Don’t follow this tragic example!

You should follow her example. If you’ve been paying attention, this is what humor writers do: turn their pain, confusion, and anguish into humor writing.

Allie Brosh

Author of Hyperbole and a Half, Brosh is quite possibly known more for her comic illustrations of herself than her writing. But the combination of her depiction of the bizarre inner workings of life and her unique self-deprecating humor as a way to deal with her depression is nothing short of astounding.

In an interview with with Terry Gross on NPR, Brosh says this about her writing style:

ALLIE BROSH: I would describe it as stand-up comedy in book form. I feel like my writing style is sort of the result of me subconsciously trying to replicate the feel of stand-up comedy. I was very frustrated when I first started writing that there wasn’t that physicality to it. There was – it was more one-dimensional than stand-up comedy, which you can rely on tone and facial expressions, body posture, and I wanted to find some way to commit that to the page. And drawing fixed all those problems.

TERRY GROSS: Another solution would have been to do stand-up comedy.

BROSH: Yes. Unfortunately, stand-up comedy is live, and my thoughts tend to come out rapidly and partially deformed. So I don’t know if I lend myself very well to stand-up comedy. I’ve always wanted to try it, though.

GROSS: Would you describe for our listeners who haven’t yet seen your blog or your book how you draw yourself and why you draw yourself that way?

BROSH: All right. So I draw myself with very crude illustrations in a program called Paintbrush. It’s sort of the Macintosh analogue of MSPaint. And I look very funny. I’ve got these buggy eyes, and I have sort of like a tube body and a little, like, triangle ponytail thing on the top of my head, and it’s a strange sort of animal-like creature.

And the reason I draw myself this way is I feel like this absurd, squiggly thing is actually a much more accurate representation of myself than I am. It’s a better tool for communicating my sense of humor and actually getting across what I’m trying to say than, say, you know, being there in the flesh. I feel like it’s – that’s actually one of the reasons why I don’t do stand-up and why I do this instead, because I can use this character to communicate and make it much more accurate and true to what I’m trying to say and true to my tone.

If you struggle to with writing humor, I challenge you to write a bizarre scenario. One that comes from a deep personal place, is self-deprecating, yet feels therapeutic. Even if you only attempt it, you are doing what other humor writers do everyday. Or at least, on the days they feel like writing…

Amy Ayres

Amy Ayres is the Web Editor & Tech Fairy at DIY MFA. She has five novels in progress and is querying one. When she is not in her office writing about terraformed planets, multiple personalities, and Irish folklore, she is hanging with her awesome tech-savvy hubby, stepson, and RubyCat. Visit amymarieayres.com. You can sign up for her Newsletter where she sends out motivational tips for new writers and her special brand of humor. You can also find her on Twitter and Instagram.

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