Make ‘Em Laugh: Five Funny Favorites on the Art of Humor Writing

As a rule of thumb, a funny blog draws readers. Humor connects us, brings perspective to serious topics, and exposes deep truths. We “Like” posts that make us laugh, share them on Facebook, tell our friends about them, and eagerly await each new opportunity to guffaw.

Despite this, humor writing can seem daunting. To demystify the process, we assembled an all-star team of beloved, boffo bloggers who agreed to pull back the curtain on the Wizard of HAs.

(What? Puns are funny! Our experts agree!)

Our distinguished panel of humorists includes:

Matt, the self-proclaimed “greatest blogger of his generation” behind You Monsters are People.
Darla, who brings the plaid and the funny at She’s a Maineiac.
Len, the enfant terrible responsible for Blurt.
Katie, proprietress and head bouncer at Sass & Balderdash.
Julie, of the often-imitated, never equaled Fear No Weebles.

Let’s get right into it. Please explain how to be funny.

MATT: Being funny is a trick of confidence. Once you’ve got people believing you are funny, you can say almost anything and they’ll take it as a joke.

DARLA: Easy — just open up your eyes and observe.

LEN: What’s funny is out there; it’s up to us to spot it. Being funny is more about recognizing funny and finding the best way to communicate that to someone else.

I think humor is something that occurs naturally in the environment. It probably should be an element, or maybe a compound. (I’ll probably be sorry I said that because if they make it a compound I’ll never remember the formula.)

MATT: Right! Get out there and see what happens. I intentionally throw myself into bizarre and sometimes dangerous situations just for the story. You don’t have to do that, but it might not be a bad idea to get off the davenport.

JULIE: This one’s tougher to swing, but being born to funny parents has benefitted me enormously. If you can do that, you should.

Do you think of yourself as funny? Is “funny” something you try for?

KATIE: I think I’m hilarious. Anyone that has even the smallest, osteoporosis-ridden funny bone needs to think they’re funny in order to really own their style of humor. The more you “try” to be funny, the more you suck at it.

JULIE: I don’t try too hard to be funny because when I do, I bomb. See, right now I’m trying really hard to think of ways to be more entertaining, and I’m getting performance anxiety. That’s not funny.

In general, though, I do think of myself as funny. That’s one of the few traits I’m confident about.

DARLA: I grew up with five brothers and had to survive somehow. It was either make a joke or get put in a headlock and suffer the suffocating farts o’ shame. Although I don’t think they thought I was very funny.

I had a cruel childhood. Most humorous people did. Thanks for bringing it up.

I had a cruel childhood. Most humorous people did. Thanks for bringing it up.

— Darla, She’s a Maineiac

JULIE: I was an overweight kid who was the tallest one in her class, with frizzy hair, buck teeth (and then braces) and glasses. I was teased a LOT. If you’re going to be teased a lot, you better have some good comebacks or you’re doomed.

MATT: As a kid I would tell stories in the lunch room or during gym to make everyone laugh…not a lot has changed since then.

LEN: I don’t think of myself as funny. I’ve had the blog going for a few years now and it still surprises me when people tell me they look forward to reading it. My family is way funnier than I am.

I was born to be a straight man. The real me is quiet. I think most people who read my stuff would think otherwise.

How do you get the funny into a post? What does your writing process look like?

LEN: The most challenging part is developing a topic. Humor is the start of most of my posts. I’m usually writing about something that strikes me as funny, so I see the jokes when I see the topic. More funny concepts come up during the writing itself. My best writing comes when I allow myself to “what if” my original ideas.

When I am writing well, my posts almost write themselves. Being conscious of my process has helped me become a better writer. It also has enabled me to sound more pretentious, like in that last sentence.

Being conscious of my process has helped me become a better writer. It also has enabled me to sound more pretentious, like in that last sentence.

— Len, Blurt

KATIE: Whereas when I sit down, I know what topic I’m going to write about, but I have no idea how or even if it’s going to be funny until I actually start typing.

MATT: I usually begin writing whether I have anything funny or profound to say about a given topic or not. I pick whatever’s been on my mind during the day. If the post ends up being funny, then I might elaborate on a few bits to make it funnier or inject a little fantasy; that’s usually when I incorporate my illustrations.

What about mixing the funny with more serious topics?

DARLA: Tragedy and comedy are tightly connected. There is nothing more freeing than talking about a heavy subject only to lighten the mood with some laughter. I truly believe laughter saves us. However, it’s a delicate process, one that shouldn’t be treated lightly. You have to gain readers’ trust, not alienate them.

LEN: That relationship definitely helps. Being able to write humor on serious topics becomes easier the better my audience and I know one another. Long-term readers come to know my voice as a writer.

Humor in serious topics is risky, but a lot of fun. A big part of pulling it off is establishing with the reader that you don’t see yourself as above criticism. Being able and willing to mock yourself is important when you’re walking the line between levity and going too far.

MATT: I think it also helps to have some ownership of the thing you’re writing about. People tend to get angry when you joke on issues that you know nothing about. It doesn’t make sense to even try and tackle a serious subject if you can’t be frank and open about your experiences.

If other bloggers want to explore humor writing, is it something they can practice? Can someone get funnier?

LEN: Absolutely. But becoming a funnier writer isn’t about increasing your funny, it is about becoming a better writer. Become better at bringing your reader to the moment you discovered something that made you grin.

It’s also important to get over the fear of not being funny. Try. Write it. Put it out there.

KATIE: We’re all always practicing — you have to. The more you practice, the more comfortable you get with your voice, the more potential you have to see more opportunities to be funny. Kind of how Madonna’s voice got better over the years.

Maybe that was just autotune. Whatever, you can’t autotune humor, it just takes practice.

You can’t autotune humor, it just takes practice.

– Katie, Sass & Balderdash

DARLA: You can absolutely fine-tune the funny by writing more and more. Then go back and cut your words down. For me, the more I edit, the easier it is to get my point across and make people laugh. People want to be entertained by your words, not put to sleep by them. Less is more. Let your imagination go to the place where the crazy good stuff comes out — then edit and give it a rhythm.

JULIE: Editing is key. For instance, right now I’m writing a post and I have only a vague idea of the direction it’s going to go in, or how it’s going to be funny. It will probably shape itself as I write, and rewrite, and rewrite

MATT: Even when you’re not writing, work to see multiple perspectives. Having a different point of view while acknowledging others is good comedy maintenance.

Learn as much as possible, too. Intelligent people are always going to be funnier; they know more, so they have a deeper pool to draw from.

JULIE: Smart always makes funny funnier.

Comedy comes in many forms — physical comedy, satire, black comedy, absurdism, stupid pet tricks, knock-knock jokes. What’s the funniest?*

MATT: Satire.

DARLA: Satire.

LEN: Satire.

KATIE: Satire.

JULIE: Satire.

MATT: Satire has to be first because it’s just so damn important. I genuinely doubt that I would want to live in a world without satire.

DARLA: I love it because it boldly exposes the truth and forces you to think.

KATIE: It gives you the chance to really poke fun at something in an exaggerated, over-the-top way that’s apt to ruffle a few feathers.

The least funny?

KATIE: There’s nothing funny about babies or animals acting like humans, because why ruin a perfectly good thing? Animals and babies are only awesome because they’re not adult humans.

LEN: Agreed. Although I think it’s important to point out that a monkey riding a dog is always funny.

(Ed. note: totally agreed.)

If I wrote a Cathy comic, I’d have her kill her judgmental mom and get over her body image problems in the very first panel.

— Matt, You Monsters Are People

JULIE: Nothing is less funny than most prime-time television. NOTHING. Even Gallagher, and he’s not even close to being funny.

MATT: This wasn’t on the list, but I’d like to nominate the “Cathy” comic strip. Cathy never went anywhere, did anything, or had anything important to say about life. She just went to the office, came home, worried about being ugly, and yelled “Ack.” If I wrote a Cathy comic, I’d have her kill her judgmental mom and get over her body image problems in the very first panel.

Any parting thoughts? Make ’em good.

LEN: Agents: I will write for food. Call me.

KATIE: The most important thing about being funny is understanding that everyone is funny in their own way, and the great thing about humor is it’s impossible to measure because it’s so subjective — so put your ruler and protractor away. As for your audience, come to terms with the reality that sometimes they’ll be laughing with you, sometimes they’ll be laughing at you, and sometimes they’ll be laughing because your shoes don’t match and your fly is down.

MATT: Support thoughtful, creative individuals wherever you find them and practice trying to be one yourself.

LEN: Be grateful to your readers. Acknowledge their comments, and return the favor if they’re writers too.

Thanks, all!

Any questions from the peanut gallery?

——-

*Note: bloggers were asked to rank the following, from most to least funny: Spit takes, Puns, British-style absurdo-comedy, Prat falls, Gallagher, Babies/animals acting like adult humans, Satire, and Prime-time television. The editors of The Daily Post acknowledge that this is not an exhaustive list and that humor is deeply subjective, although we were heartened to see than “Puns” ranked fairly well across the board.