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When I first entered the fold at The Prompt, there were a few writers I instantly gravitated toward—some because of their writing, and some because of their personality.

For Dennis William, it was both. Dennis and I struck up an immediate rapport during meetings, bouncing good ideas off each other and making each other laugh. It’s strange to think I’ve never met Dennis IRL, because I feel like he’s a real friend. I hope one day we’ll get to share a beer and do what we do best—talk shit.

Rather than send him a bunch of questions over email, I thought it’d be fun for us to do the interview live over Zoom. What follows is a transcript of our conversation.

What was the first time you remember writing something and went “oh wow, that was fun?” How did that writing bug develop for you?

I remember having to write our own Frog and Toad book in elementary school, but I don’t remember getting the itch from that. I took a creative writing class in high school, and it was probably that.

I don’t know how old I was, but I read something from Graham Chapman from Monty Python and he had some sketches in it. And I was like “oh yeah, people have to write these stupid sketches that get turned into TV.” So I started writing scripts like that. Two of my friends in junior high would write me notes, and each of us would add lines of dialogue like a script. It’d be like Valerie said this. I would write back, but I was by myself, so I’d invent someone else and what they said. I said this, and Clive said this.

Then I took creative writing in high school and I was like “oh, I’m good at this,” and I started with poetry. You can write a poem in like, an hour, so you can say “oh, I had a thing, and it’s done.”

You tend toward satire, snarky. Has that always been your wheelhouse?

*Holds up copy of Sex, Drugs, and Cocoa Puffs by Chuck Klosterman.* Because I’m ripping off this person.

Is that what it is?

I actually met him at a bar here. I was on a first date, and I looked behind me, and I was like “that guy looks like Chuck Klosterman.” And then I heard him talk and I was like “oh, that’s absolutely him.” My date came back from the bathroom and I was like “this guy on my phone, that’s him, right?” And she was like “yeah. Are you going to say hi to him?” And I said I didn’t know, and she was like “you have to.” So I went up to him and said “hey, sorry to bug you, but I love you, I’m a big fan. I took an essay class in college and did a presentation on one of your chapters.” He was super nice.

But yeah, snarky funny, personal essays is what I like to do. I would like to be better at writing fiction. I try it, but I don’t know how good I am at it. But that’s my edgy stuff, yeah.

What is it about that genre of cultural commentary, satire, that appeals to you?

Probably that with fiction, I’m worried that the thing I’m making up is boring. It’s hard for me to come up with twists in stories and stuff like that. I’m not clever enough to come up with a good twist. If I read an Elmore Leonard book, I’m like “how did you come up with this?” So you’re not inventing anything, and you just have to describe what happened in an interesting way, which seems like an easier thing to do than just inventing an interesting thing.

I enjoy dark humor and being able to comment on the world or my life or things that have happened to me. It’s a funny way to describe things, but just because there’s a little darkness to it doesn’t mean you’re being negative. I feel like I still write positive things. I’ve joked with people that I’m glad they hang out with me because I’m negative, and they’re like “you’re not negative, you’re just realistic.”

I think dark humor is a fair label for your work sometimes, but I don’t think you write things that are like “we’re all fucked.”

Because I’m a teacher, it means I have to be optimistic, right? Otherwise, what’s the point of my job? But when stuff sucks, to me it helps point out that it sucks, and then I can move on. That’s the kind of stuff I like to read—like Defector and the former Deadspin—because when they’re talking about sports, when there’s something gross or slimy about it, they didn’t shy away from it. Like, here’s a thing that sucks about a thing that we love. 

One thing I notice about your stuff is that you play a lot with form. I don’t know if that’s a conscious choice, but a lot of them can be listy or you had the roller rink story that was predominately dialogue. Then you have stuff that’s almost avant garde. The Cooper Kupp thing.


Let’s talk about that first. What the hell is up with that story, and why did that even happen?

Cooper Kupp is a sequel to Mads Mikkelsen. I did Mads Mikkelsen through the alphabet. But then Kelaine was like “we need Super Bowl content,” and I was like, “Cooper Kupp.” He’s got an alliterative name. I can just rehash the same joke.

I don’t know why I did the Mads Mikkelsen one. I think I just heard the name and started thinking “what if you could do Dads Dikkelsen, Kads Kikkelsen.” Like, oh, those are funny phrases. It’s good because in the middle of the alphabet, it’s not that funny, but then the joke comes back around.

For me, that’s taking a risk. You’re putting out a form that’s like “what the fuck?” It’s like a Family Guy joke that goes on so long. It’s funny for the first three letters, and then it’s not funny for a good 30 seconds, and then it’s funny again.

Some of them it doesn’t work, like with E, I don’t even know how to say this, but then you get to one that’s like Pads Pikkelsen. Like, that’s just a funny sounding phrase. My humor—even in conversation—is what’s the dumbest thing that I could say? Sometimes I try to be aggressively stupid.

One time I was playing Catchphrase with people, and someone on my team said “not salt but…” and I said “Spinderella.” My ex was dying laughing, and she said “the best part about it is you knew the right answer, but instead you found the funniest wrong answer in a split second.” To me, Mads Mikkelsen and Cooper Kupp are like that.

That was just a joke where I just stretched it through the whole alphabet. If I wanted to sniff my own fart about it, when I was in middle and high school, I thought Andy Kaufman was hilarious. I read Lost in the Funhouse, and it talked about his mentality of I’m going to do something until it’s not funny and then I’m going to keep going and force people to deal with the fact that the humor is gone but eventually it’ll come back. 

It’s that tension you get with a joke, but without the release.

I don’t think I put that much thought into Mads Mikkelsen or Cooper Kupp things. But the quarantine parodies I did about social distancing. Those were closer to where I went “here’s an idea that exists” and I was the one who grabbed onto it. Those were easy to write.

Usually, I just come up with an idea and go with whatever the best format to convey the idea is. With the roller rink story, I guess it just felt right for it to be mostly dialogue. It was the more interesting way to tell it.

Talk to me about how you get to that place. You’re on a Prompt call, the prompt gets thrown out. Do you just go “what’s the most absurd thing?” Is it that?

Usually it’s like the ideas that I have and which one seems like it will be the most fruitful. I don’t really labor over them. If I think I don’t really have anything for this particular prompt, I don’t do it.

In terms of writing process, revision, do you work through a process? Is there one you adhere to? What does it look like for you?

Since there’s the time crunch for The Prompt, I usually see which one of these ideas has lightning that can strike me. Which one has a half-formed idea already attached to it. Then I sit down on my bed and write it, probably with the TV on as background noise, probably have a beer to lower my inhibitions to write.

I like writing by hand just because the time it takes you to write gives you more time to think about what you’re going to write next. You type so fast, sometimes you’re like “cool, that sentence I had is down already, and now I have to find the next one.” Then you have to transcribe it, which forces you to revise.

I do a lot of editing and revising as I go, which, when I’m teaching my students, I have to say “do as I say, not as I do.” As I’m writing, I’ll go back to a paragraph and say “I need to fix that.” When I was writing papers in school, I’d start with the paragraph that I knew I could write, like, I know I have stuff to say about THIS. Then I’d go to another point, and jump to another. As I got bored of a chunk, I’d move on to another one, and then go back to finish it.

You’ve lived in a lot of different places with different vibes.

I’ve lived in three places.

Yeah, but in terms of geographically, they’re pretty significantly different, right? Do you feel like that’s influenced or dictated the way that you write, and also the way you see the world?

Definitely how I see the world. Now I feel like I have to consciously not be judgy of people who live in their hometown. Most of my best friends still live in our hometown, but also my hometown is a college town, so it’s less sad to stay there. But it’s definitely changed my worldview. I still identify strongly as a Midwesterner, but now I have to add “but I lived on the East Coast for six years,” so I’ve been East Coast-ified.

Coming to Portland was a change. People were like “How do you like Portland?” and I was like “if everyone could just move half a step quicker, that would be nice.” And people want to chat, which is very Midwest. Even when I go back to Kansas, I’m like “let’s wrap it up, people.” I feel like my walking pace is normal again, like I’m not just power walking everywhere like you do in D.C.

You can learn a lot about people by how fast they walk.

Right? Living in different places has allowed me to understand how people are different in different locales—the mindset, the culture of different areas. When I walk into a store on the East Coast, the worker is like “hi, welcome to the Gap,” and they go back to their phones. I like that. I don’t need you to help me more than that. This is not my first rodeo. The East Coast has this reputation of being rude. I think they’re all really nice—the window is just smaller.

I saw a great tweet that was like “the East Coast is nice but not pleasant; the West Coast is pleasant but not nice.”

I feel like I would be remiss if I did not address your social media presence.


You’re pretty prolific on Instagram. You’re one of my favorite follows. What draws you to Instagram? What’s your thought process for what you post? Is there a thought process?

No. When I joined Instagram, it wasn’t owned by Facebook, so it was just like “post cool pictures.” So I try to be a cranky old man in that way and just post things that are cool. Like I’ll post VW Vans of Portland.

For IG stories, I was like “I don’t need to do this.” And then for a year it was only Oh, Tippi. [my beagle]. 

That was my follow-up question.

I thought as soon as you said “Instagram presence,” I was like “this is about Tippi.”

What’s the origin story there?

I saw the SuperZoom filter, and I did one on Tippi because she was sleeping, and I was like “that’ll be funny if I ONLY do this.” People will be like “oh that’s sweet,” but then by like the fifth one, they’ll say “oh, this is dumb.” And then the tenth one, they’re like “okay, I like it again.”

Again, it’s the coming back around again humor.

My ex was like “no one’s going to watch all of these,” but they do. They do. And I have friends who’ve never met Tippi who are like “how’s Tippi?” Someone recently told me they saw a dog and thought “oh, Tippi.” People that have never met her, that’s a thought in their heads. The brand is strong.

But then I succumbed, and now I post like—

Angry Communist stuff.

Yeah, aggressively woke tweets.

There’s been points where I’m like “Is Dennis a communist?”

Yeah. I mean not a communist, just a socialist. I told my dad recently that I was done voting for Democrats for president. It’s clear they just don’t give a shit. They only want to do what it takes to get re-elected, so I’m done.

So now, it makes my Instagram stories lamer, because it’s not just super zooms on a beagle. But I don’t know. I just share shit that I think is important and/or funny. There’s not a ton of thought process. It’s social media, who gives a shit?

Although people now send me stuff on social media about Old Bay, which I appreciate. Old Bay isn’t a thing out here, so when I ask for it, people get confused. When people ask me what Old Bay tastes like, I tell them it tastes like rust and paprika. So that’s another part of my brand. Oh, Tippi and Old Bay.

Last question: Your favorite piece of writing advice or inspirational quote or something that compels people to keep going.

I now have a lot of inspirational memes saved on my phone in the event that I need to decorate a classroom at some point.

In the event you need to mold young minds.

The one I really like is “Be brave enough to suck at something new.” During quarantine in 2020, I bought a ukulele and learned to play it. I would not describe myself as a good singer, but I play the songs and there’s no one else to sing them, so I record myself and I share it. And someone I’m seeing is like “you inspire me to do things even though I’m not that good at them.” And I was like “are you saying I suck at the ukulele?” Like, I’m not good at it, but it’s fun. And I don’t think everyone has to be great at something to do it, as long as it’s fun. Looking through the lens of teaching, I say that to my students all the time. It’s like, of course you’re not good at this. If you were, then what the fuck am I here for? I need someone to suck at this so I can teach them. Your job is to be bad at this now and better at it later.

Then there’s this other one: “It’s always the motherfuckers with no magic trying to tell you what to do with yours.”

Sam Hedenberg

Sam Hedenberg is a humor blogger living in Northern Virginia. When he grows up, he wants to be a writer or quarterback for the Philadelphia Eagles.

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