Scott Dikkers, Founder of The Onion, on How to Write Outrageously

A classic interview from the archives

Good news. I’m co-teaching a humor writing Zoom workshop with The Onion founding editor

Scott Dikkers

.

“Comedy for All: 6 Ways to Make Your Writing Funnier.”

WHEN: Sat March 22 at Noon CT.

FREE for all who sign up.

This workshop is for writers of every kind—whether you write fiction, comedy, memoir, essay, narrative nonfiction, copywriting, or whatever.

It will slightly resemble a workshop of a similar name that I previously taught. Except this time Scott is co-teaching, so it will be even better and there will be a bunch of new material.

We’re also planning to deconstruct and edit some humor writing toward the end of the workshop, plus there will be Q&A.

Sign up here.

If you sign up…

• The workshop list is my personal monthly list, separate from Comedy Bizarre. Look for a confirmation email, and be sure to open that email and click “Yes, subscribe me” in order to join the workshop. Then you’ll get workshop details.
  

• If you’re already on my personal monthly list, however, you’ll immediately get the workshop confirmation.

Hope to see you there!

---

In honor of this upcoming workshop, I’ve dug up an interview from the depths of my archives. Way back in my salad days of 2016-2019, I ran a WordPress site about humor writing, and I interviewed a bunch of writers I admired. Happily, Scott let me interview him.

That WordPress site is long gone, but I re-read the interview, and I still like it. So, now’s a great time to re-run it.

(By the way, be sure to subscribe to Scott’s awesome Substack,

No Dikkering Around

)

Enjoy!

---

[interview originally published in 2019]

Do you want to write outrageously and find an audience that loves you? This interview is for you.

Scott Dikkers founded The Onion in 1988, and TheOnion.com in 1996, and has served as its owner and editor-in-chief, on and off, for many of the past 25 years.

Scott also co-wrote and edited The Onion’s first original book, Our Dumb Century, which sold more than a million copies, debuting as a #1 New York Times and #1 Amazon bestseller.

Scott and I talked about how to grow as a writer and build something incredible. We also discuss his two newest books:

• Outrageous Marketing (a behind the scenes look at creating The Onion), &

• How to Write Funny (the best comedy writing book I’ve ever read).

Find out more about Scott at www.scottdikkers.com

---

Alex Baia: Something I loved in Outrageous Marketing was learning how The Onion’s comedy and writing voice evolved over time. You started in the late 80s with various oddball gags, like interviewing drunk people as the “drunk of the week.”

It took a few years to find the classic deadpan AP journalism style, with The Onion becoming the bumbling, faceless news corporation. When did you realize that you’d found The Onion’s true voice, and how did you know, “okay, this is our brand.”?

Scott Dikkers: Thanks so much! Well, that was a glacial process. It probably took place over a period of 2–3 years, I’d say between 1995 and 1998. By then I definitely knew what the brand was, after making a ton of mistakes trying to make it into something it wasn’t, namely a wacky college humor publication. What it was was the first of its kind: a humor publication masquerading as a parody of a newspaper.

There was a lot of R&D before then. We did all the things you mentioned. On top of that, we made a sketch TV pilot, a wacky comedy CD, we produced a TV show for MTV, and a ton of other goofy things. That said, we did a lot of things right. We started doing the Onion Radio News in 1990, and it was pitch perfect from the beginning. It was a straight parody of AM-radio news, and it was incredibly funny. It was just Onion stories condensed into short radio news bits read by P.S. Mueller, a local cartoonist who had read AM-radio news as a side job for years. So, he knew how to play it straight.

We also made some really good in-house ads for The Onion that we ran in the paper that touted The Onion as more trustworthy than the New York Times and such. Those were really funny. Other ones were serious ads saying, “Attention Educators,” promoting The Onion as a classroom teaching tool so kids can learn about the world, stuff like that. So, the grain of the true Onion voice had been there for a while, but I wasn’t directing all firepower in that direction until the mid-late 90s.

You have a great story in Outrageous Marketing about getting your comic, Jim’s Journal, first published in newspapers. You sent the comic to The Daily Cardinal — one of the largest and oldest student newspapers — every week. They didn’t ask for it, and you didn’t ask permission, but they started using it.

I actually submitted Jim’s Journal to The Cardinal and they decided to run it on a trial basis. I sent it for free to a ton of other college newspapers and did what you said — just sent it unsolicited for months as if they had already signed up to receive it. And a lot of them started running it. And once readers were hooked, they couldn’t stop! It was a good strategy.

This was in the late 1980s when artists and writers relied more heavily on gatekeepers. Now we’ve got blogs, podcasts, YouTube, Medium, etc. Do you advise today’s writers to use this principle of, “You don’t need permission to apply for the job. Just show up and see what happens.” Still the same idea?

Absolutely. I advise anyone who will listen to be all over that shit. If I were starting out, I’d be all over it. (I basically am anyway!) It can feel like your throwing your great creative work into a void at times, but now you know how it felt working at The Onion from 1988–1998. These things take time. I think it actually takes less time now, with the democratization of the media that we’ve seen. Yes, there’s a lot more competition, but most of it’s not very good, and it can feel like a merit-less popularity contest at times, but on the plus side it’s easier to get noticed nowadays when you’re doing truly exceptional work.

---

I’m curious about your take on quitting. How should writers who are building their thing distinguish between a good project that just hasn’t taken off yet vs. a project that really isn’t going anywhere? Is it that sense of some forward progress, however small? Or that, if nothing else, the work is getting a little bit sharper, day by day? Or maybe it just comes down to whether you love it and get joy from it, and nothing else matters?

This gets to the core of the whole thing. And you have it absolutely right. If you love doing comedy, then you’ll never quit. Those who succeed keep doing it, and change their approach when it’s not working, and they get better. Over years and even decades, they get good enough to make a living at it. If you don’t love it, that’s a long slog. If you do, it’s not much of slog at all. It’s just your life, and your passion, and you’re a success even before you make money at it, because you love what you do.

If you love doing comedy, then you’ll never quit. Those who succeed keep doing it, and change their approach when it’s not working, and they get better. If you don’t love it, that’s a long slog. If you do, it’s not much of slog at all. It’s just your life. — Scott Dikkers

A lot of writers and comedians are trying to navigate the gatekeeper vs. build-it-yourself spectrum. On one end of the spectrum, you might want to write for, or act in, a network TV show, so you need to get picked by a gatekeeper. On the other end, you could say “forget the gatekeepers,” and build your own comedy thing.

But you sort of did both. You clearly built new things, but you also strategically used old-school media, e.g. publishing an Onion book with a traditional publisher, testing the waters with TV, etc. What’s your advice to newer comedians and writers who are trying to decide on building their own thing vs. going with “the entertainment/media establishment” vs. a mix?

I have a whole philosophy about this that I’m going to put into a book. I do a guest lecture at the Harold Ramis Film School in Chicago where I talk about this exact thing. It’s been an extremely well-received lecture, so I decided I need to write it down and publish it. It started as a “How to Pitch Your Ideas” lecture, but it’s become more than that. It’s about the pros and cons of building it yourself vs the establishment.

The bottom line is that you should be doing both. At first, I’m guessing only the first option will be available to you, and that’s fine. Take advantage of your youthful passion and make shit! The reason you should be doing both is because you should love doing it. If you don’t love it, why are you doing it? I always worry about people who dream of working on a TV show but aren’t willing to produce their own TV show on youtube or as a podcast. If you really loved it, you’d be doing it at every waking moment, by hook or by crook. You wouldn’t be waiting for someone to give you the opportunity to do it. And nowadays, when you do it yourself is when bigger opportunities present themselves. If you’re just sitting around waiting to hear back from submissions all the time, you’re most likely not going to get far.

One of the principles in Outrageous Marketing is “Use quantity to achieve quality.” You explain one way this manifested at The Onion: the writers invent hundreds of headlines to find the really good, usable ones.

And in How to Write Funny, you tell writers to give up the fantasy of “the genius who nails it on the first draft,” and instead to unleash their clown brain and over-generate material. Only then should writers switch to “editor brain” where the good material gets selected and honed into gold.

You also point out that most humor writers have too much editor brain and not enough clown brain. You mention some tools writers can use, e.g. free writing or “morning pages” (from Dorothea Brande’s Becoming a Writer). In your own writing life, which tools and practices have given you the right balance between clown brain and editor brain?

I’m so pleased you did some research and read my books before asking these questions! The tools are for developing the Clown and Editor brain. Once they’re developed, you just have to use them (the two brains, not the tools).

For me, since I’ve been doing this for a long time, I don’t really need to use the tools anymore to develop my brain. But if you’re not there yet, I spell out all the tools in How to Write Funny. These are the tools I used to get where I am, and they’re the same tools I’ve seen other writers use successfully in one form or another.

For developing the Clown I advise the morning pages, jotting down ideas in a notebook when you think of them, and just writing a lot. To develop the Editor brain, you have to know how to use all 11 Funny Filters and know the best practices for each. In Book 2 of the HTWF series (“How to Write Funnier”), I get into more detail on how to get useful feedback from people, which also helps develop the Editor brain. To develop dexterity between Clown and Editor, I recommend using the three methods of joke creation I spelled out in HTWF: Filtering, Finessing, and Divining.

I advise people be dextrous (be able to switch rapidly between the two parts of the brain) because you never know which one you’re going to need, and when. If I have to crank out a rough draft on deadline, I can’t spend several days priming the pump by doing the “morning pages” exercise. I need to be able to produce on a dime. And when I need to assess what I’ve done but can’t get access to a team for feedback, I need to switch to Editor brain fast and be able to trust it without suffering from the pitfalls of relying too much on Editor brain (writer’s block and failure to produce).

So, about writer’s block, which people debate endlessly: is writer’s block real? how do we deal with it? From the perspective of Clown Brain vs. Editor Brain, there’s not much mystery here. Clowns never have comedy writer’s block, because to be a clown is to be an infinite comedy engine. The clown has no filter, no need for judgment, no need to stop playing. In How to Write Funny you’re giving people the tools to access these two brains. But if you can access both brains, and switch quickly, writer’s block becomes less of an issue.

Truth. Writer’s block is real, but it’s self-inflicted, and easily rid of.

---

On the topic of “genius,” I’m curious where you stand on the importance of innate writing talent vs. deliberate practice. By “deliberate practice,” I’m thinking here of books like Deep Work, The Talent Code, Talent is Overrated, Mastery by George Leonard, etc.

Take the hilarious writers you edited at The Onion over the years — what percentage of their hilarious output to you attribute to sheer innate genius versus the right kind of deliberate practice over time?

I’m in agreement with those books. There’s no such thing as talent. Everyone who’s “talented” learned their craft one way or another. Maybe they just learned it earlier. Everyone I hired at The Onion (which is almost all of its writers over the years) came in with zero comedy experience.

Without naming names, I can tell you that some of the people who, at first, seemed the most comedically tone-deaf have gone on to become the most successful in the comedy business, winning tons of Emmys. That’s because they worked harder. Some of the most “talented” haven’t gone far, largely because they didn’t feel they had to work as hard. They felt things should just come naturally to them. Things don’t. You have to work for it. Talent isn’t like IQ. It’s not fixed. You can keep getting more talented if you work at it. Actually, I guess they now say IQ isn’t even fixed.

There’s no such thing as talent. Everyone who’s “talented” learned their craft one way or another. — Scott Dikkers

Any specific habits or mindsets — aside from sheer hard work — that you noticed in these writers that contributed to their progress? I mean things like openness to criticism or how they sought mentorship, etc.

Hard work was by far the determining factor. But they had other qualities to varying degrees: they loved doing it, they were pleasant to work with, they were reliable, and they had an open mind about improving their work.

In each type of comedy I’ve performed or written, I’ve noticed certain “Checklist” questions the artists frequently ask themselves. In improv, “What’s the game of this scene?”, or “If this is true, what else is true?” In conceptual humor writing, “What’s the main premise of this piece?”, or “Is this heightening enough?”

When you edited The Onion were there any questions like this that came up frequently in the writer’s room?

Yes! “What’s this saying?”; “Is this the best joke that can be made about this subject?”; And my favorite, “Yeah but will it make people laugh?”

In How to Write Funny, you categorize prose humor into a spectrum from least to most sophisticated. It goes from sub-literate chimp humor and kid jokes on one end, to multi-layered humorous prose and satire on the other end.

To get all the way to the right end of the spectrum, we need to use subtext. The subtext is whatever you have to “get” to get the joke. All jokes have some subtext, but in satire, the subtext comments substantively on the world. It’s showing the reader how something is terrible or amazing or unjust or absurd. At the highest level, satire offers deep truths about humanity, the universe, or existence.

I can think of several great satire pieces with fairly obvious subtext — this is one of my all-time Onion favorites. Other times (perhaps less frequently?) there’s a wicked good, layered piece of humor, and there is deep subtext, but it’s less obvious what’s going on. So how transparent a subtext does writing need to hit the highest levels? Do all readers have to get it?

No, all readers don’t have to get it. That’s the beauty of it. A piece in The Onion like this (warning: NSFW) is a classic editorial that just about anyone is going to laugh out loud at, regardless of their sophistication level. They may not even be aware of the subtext (that ignorant bigots are often repressed homosexuals). The subtext may even be about them, and they won’t know it. Nuthin wrong with that! It’s why satire is the most broadly appealing humor category.

Everyone from kings to groundlings gets something out of it, as Shakespeare said. The subtext is for the “kings” (the sophisticates), and it can be difficult for even those people to articulate, because we’re rarely taught to define subtext in comedy, and we don’t really want to. The groundlings certainly don’t. They just want to laugh and enjoy themselves. But as a creator of humor, it’s super valuable to be able to define and articulate your own subtext. You want to be sure it’s as objectively relatable and accessible as possible. Of the two examples you mentioned, I find the subtext of the latter easier to suss out. Everybody’s different!

Final question. You mention in Outrageous Marketing being a believer in self-help and self-improvement. I am too. It’s enjoyable to mock, of course, because it can get silly. But I read some self-improvement books because they help me get in the right headspace and deal with negative thought patterns.

Has self-improvement helped you as a writer in any specific ways? Any particular books or practices you’re willing to share?

I also like mocking self-help. I wrote a book called You Are Worthless years ago that continues to sell well. I called it the first self-hurt book.

But, yes, self-help has been instrumental in my life. The first I ever encountered was an Earl Nightingale audio series, a pretty basic one like “the rules of success” or something like that. I was broke, had no job, and had no prospects — certainly not in comedy or the entertainment business. I listened to that and inside of a year or two I was a successful cartoonist with a popular daily comic strip and was owner/editor of The Onion.

Later I got into Tony Robbins. I listened to most of his stuff and I think he’s the best. Really powerful strategies for being more productive, more successful, for managing your emotions — that’s what sabotages so many people. They’re not in control of their own emotions. So sad. Since then, I’ve partaken of so much self-help I’d be hard-pressed to remember much of it. Jay Abraham was one. I’ve kept up with Tony Robbins’ stuff — his stuff keeps getting better. I never went to one of his events. I prefer the audio.

I never did Landmark Forum or any of that. I went to therapy for a while, I got this amazing book “Raising Your Emotional Intelligence” by Jeanne Segal that changed my life and kind of obliterated a lot of my social anxiety, personal flaws, and emotional baggage. I think of this stuff as self-improvement more than self-help. I’m constantly taking courses in areas of personal development that I know I could be better in. Last year I spent tens of thousands of dollars on courses in business, online marketing, facebooks ads, amazon ads, self-publishing, building a business — you name it.

You might think I knew all this stuff because The Onion and AV Club (which I also founded) have been such successful businesses, but you have to remember that I was never in the business or marketing department at The Onion or anywhere else. I oversaw jokes, and jokes were all I knew. So, I need to learn all this business stuff to get better at it when I embark on new projects, like all the books I’ve been writing and self-publishing, my How to Write Funny podcast, blaffo.com (a humor site I started), and the “Writing with The Onion” training center I created at The Second City in Chicago. Nobody’s doing that for me, so I have to learn it!