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:

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.

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  1. The Daily Post,
    I usually refer to Madame Weebles as blogging royalty.
    Le Clown is also a big fan of Darla and Funny Posky.
    Le Clown


  2. Awesome advice you guys. I know I’ve done my best work when reading my own writing makes me laugh. My husband thinks that’s weird, but if I don’t think it’s funny, I don’t publish.


    1. Cheeky Diva – I feel the same way. If I truly laugh at one of my posts, then I know it’ll make others laugh to. Well, except people who suck, they never laugh.


  3. “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.”

    Darla, never was this more evident than your post extolling your desire to procreate with Jason Bateman. Kudos to you, woman! You are one of my faves.


  4. My blog is mostly humor writing, and I swear, the more annoyed or frustrated I feel about life, the easier the good humor flows. Not a bad deal. Great post, thanks so much!


  5. “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.”

    Thanks for the reminder, Darla! Such good advice: edit, edit, edit.

    And thanks to The Daily Post and Michelle for bringing my attention to MORE humor bloggers!


      1. Ditto, ditto, ditto, ditto, ditto, ditto, ditto. I don’t think I could ever stop saying how true it is that one must edit everything over and over and over again to eliminate the kind of wordiness that sneaks into most of our writing, despite our best efforts to make sure it does NOT sneak in, because that sort of thing is very annoying to readers who really appreciate brevity, which is the soul of wit.


      1. A pun has to be of a certain quality. It’s hard to say what that quality is. I had a boss who used to say “I know it when I see it.” I hated that guy, but yeah it’s like that.


      2. I heard that we can’t get an accurate count on the number of troops staying in Afghanistan for 2014 due to the tally ban…


  6. Great answers from all, including two of my favs, Darla and Weebs.

    The hardest thing for me to get past was the difference between telling a story and writing one. The humor has to be set up completely differently.


    1. Thanks Elyse! You’re so right—the timing is completely different in writing vs talking. Otherwise it ends up being one long run-on sentence where you can’t really process the information because there’s too much being given at once and there really isn’t any setup of the scenario and you can’t really tell when the money line is coming because there’s no warning in the form of a comma or a new paragraph or new sentence or something like that.


    2. For me, I work hard on the rhythm of a post so people forget they’re reading and just go with the flow and then Bam! hit them with a surprise or two. Elyse, you are one of the master storytellers.


  7. I have a reputation for telling a lot of funny stories, bizarre things that have happened to me. I think i am yet to transfer that skill in to my writing, but am very keen too. Thanks for the great post! Food for thought.


  8. I 20000000% agree with Julie in that “Smart always makes funny funnier.” It’s why I don’t think people can become funnier just by enrolling in an improv class or some equally ridiculous thing. You need to experience life, and enrich yourself through meaningful interactions. I do this by side hugging my television during Real Housewives reunion shows.


    1. Is there anything more embarrassing than bad improv? Because I don’t think there is. My life experiences have greatly contributed to my funny. And by life experiences I mean sitting on my therapist’s couch sobbing hysterically every week.


  9. One additional thing: anything that really makes me laugh involves misdirection. You have to get me going, thinking one thing, then jerk me the other way, suddenly. I think this is one of the reasons Arrested Development is coming off so lukewarm in 2013. People expect certain things from it and it’s serving them up, as expected.


    1. I agree! The funniest things are when you’re in one ‘frame’ and discover all of a sudden that you’re in a different… all your expectations get thrown off and you see a new connection.


  10. Reblogged this on funnity. and commented:
    Well, I just thought this post was quite befitting to the branding of my own blog, and for me, the most important thing about writing about humour is that the writing itself is enough to make you laugh.

    And, check 🙂


  11. There was a guy in my high school who was really funny. As a result, he was really popular. I thought I’d discovered the secret of life! Get people to laugh and they’ll want you around. Being funny is also an aphrodisiac. Seriously. But analyzing humor is a tricky thing. Like any art form, humor is purely subjective. I saw my very first episode of Mike & Molly this week—a show that’s a huge ratings success—and I sat there stone-faced. Poor Swoosie Kurtz! A great stage actress reduced to muttering those terrible lines!

    I’m sorry…what was the question?


    1. Being funny is an aphrodisiac? Damn. You wait until I’m 51 to tell me? Thanks a lot. This would have been good to when I was 20. I’m marking you down one letter grade for being tardy.


  12. I do slip in the occasional joke here and there but it is super hard so instead, I try to write as if I am talking to the reader. Some people like it other people don’t. Meh. Thanks for the cool blog post on humor. I love Sass and Balderbash and She’s A Mainiac!


    1. Sounds like a winning formula to me! I had a reader of my last blog tell me that reading my posts was like sitting down for a cup of coffee with me, and I took it as the highest compliment.


    2. I love you back! And can I also just say for the record, I love when people refer to me as Sass & Balderdash. Makes me feel a lot cooler than I am…


      1. Aw, there’s so much love ❤
        Blogging does make the person much cooler. Its a good pick up line. It's like that episode of How I Met Your Mother when Ted tried to get dates by saying Hey, "I am Ted Mosby, Architect."

        Katie, blogger of Sass & Balderdash. See? Now you're sexier.


  13. Ok. I am here to say something nice about Oma (Len) he has brought new meaning to art for many people and his stick figure drawings have very witty and sometimes wily smiles.


  14. To Len’s early point about humour being an element, for a very brief period, one of the elements in the periodic table was Ha (hahnium, 105)…unfortunately, that was later replaced by the significantly less funny Db (dubnium), which was NOT named for a former American President.

    For now, we’ll just have to settle for the jolly old elf of elements: Ho (holmium, 67).


    PS I’m juvenile, so I smile at Pu, as well (plutonium, 94)…unless, of course, it is part of a bomb.


      1. in a brief moment of anal tentativeness, I googled that and it is true. Funny and smart are not mutually exclusive. Funny and chemistry have been, until this comment.

        Juvenile is a fine thing.


    1. Q: What do you say if you get hit in the head with a gold ingot?
      A: Au.

      Yup, I just made that up. I think. Unless someone made it up without me knowing it, in which case I should still get partial credit.


  15. This was so fantastic, including but not limited to the monkey pic and Wizard of HAs. (NICE, Michelle. NICE!)

    Open question: Do puns top satire for anyone? …Anyone?

    It was very comforting to hear about everyone’s editing process. I read these hilariously gifted writers and think they just pop out those posts like I pop the button on my jeans. …I’m still wicked jealous, though. “Thanks for bringing it up.” You slay me, Darla!


    1. In my mind, puns are the funniest things ever. Well, almost. This animated gif of an old timey boy riding a turtle is the funniest.


    2. Puns are a VERY close second to satire for me, although it’s they’re really kind of limited in their use. But if I could, I’d use puns all the time. Is that wrong? Because seriously, my blog would be just lousy with plays on words. Sheer PUNDAMONIUM.


    3. thanks, JD! The wicked jealousy is mutual. I’m wickahd jealous of everyone.

      Puns was a VERY close second for me.

      Followed by animals dressed up as Gallagher.

      Actually, I only said satire was my favorite because I wanted to look smarter. And I failed miserably. Thanks for bringing it up, JD.


  16. I’d like to be funnier but it usually takes me days to think of a great line. Sort of anticlimactic.
    I’m always amazed at how Darla and Blurt keep me laughing.

    Going off to check the other bloggers now…


  17. Here’s another tip: watch commercials, then write what you see. You’d be amazed at the hilarity you can get out of paraphrasing a TV commercial. That’s actually probably half of what I do on my blog, actually.

    As to what I find funny: Robert Benchley, as well as Bill Cosby. Observational and anecdotal humor, with just a bit of absurd hyperbole.


  18. From Julie: “I was teased a LOT. If you’re going to be teased a lot, you better have some good comebacks or you’re doomed.” So much truth here. The best way to be funny: have a tortured childhood. My signature snarky “voice” that comes through in my blog started developing on the elementary school playground out of necessity.

    I am still trying to reconcile my abhorrence of bullying with my love of comedy. If we can find a way to end childhood bullying, while still guaranteeing that the weirdo misfits of the world will continue feeling angsty enough to grow up and be hilarious, I’m in.

    If we can bring back polyester pants and home perms, I think that would help.


  19. You know WordPress, I am never going to get any work done, because you keep distracting me with all these good bloggers to follow. Damn it! Why do you people have to be so smart and funny?

    I came up with the pun ‘momniscient’ the other day (as in: “Mom, how did you know I was the one banging on the window?” “Because I’m momniscient.”), but it’s already taken.

    How do you humor writers keep it up, when there are so many funny things that have already been written? Do you just not use Google?


    1. Oops, sorry, Kylie, didn’t mean to reply to you with that. Hi! How are you? Also, I think you should get credit for “momniscient” anyway because you didn’t know it had already been taken when you thought of it.


      1. Ha! Thank you. It WAS a moment of brilliance that I will always look back upon with pride, just like the time I “came up” with Fictionary to capture all my neologisms, forgetting that was an actual trademarked game. Here’s to originality!


      2. Kylie, I’m giving you credit for momniscient as well. Madame Weebles and I are panelists which means we are the deciders of such things.


  20. Great idea and excellent execution.
    Well done to all of you. Thanks for the generous sharing of your funny secrets. My most talked about writing has been funny stuff. Most annoying because I can only seem to manage it once a year!