The lords and ladies of LOL: Inside the minds of America’s top humor editors

An exclusive look at the gatekeepers of contemporary comedy writing.

It’s probably not a surprise that comedy writer hopefuls follow humor editors on social media, hoping to glimpse what tickles their funny bones. Of course, the only evidence I have of this is my own cyberstalking. After trying to land a clip in McSweeney’s Internet Tendency for six years, I added a column in my Tweetdeck for the site’s editor, Christopher Monks.

I learned that he liked baseball, lived in Massachusetts, and tweeted from waiting rooms a lot. Occasionally, he vented about asinine responses to his rejection letters.

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Most articles featuring humor gatekeepers like Monks and his peers focus on the do’s and don’ts of pitching and tips on how to get published, which still leaves an unanswered question: Who the hell are these people sending us all these damn rejection letters?

I decided to find out. Here I give you as much as a 90-minute individual phone interview could unearth about the lives of humor editors at McSweeney’s Internet Tendency, The New Yorker, Weekly Humorist, Robot Butt, The Belladonna, and Splitsider. I hope we can learn something that’s just as – if not more – valuable than what makes them say “yes” or “no.”

Christopher Monks, McSweeney’s Internet Tendency

Christopher MonksMassachusetts, 1969: The Monks add a new member to a tribe of Irish-Catholics who seemed to have humor in their DNA.

“They’re the funniest people I know,” says Monks, editor of McSweeney’s Internet Tendency.
“I think I owe a lot of my sense of humor to them.”

At dinners, family members often made puns that spawned five-minute riffs around the table. Other times, they played practical jokes on each other and friends.

The Boston native recalls one stunt that his father pulled on a friend whom he picked up from the airport.

“My uncle was stationed somewhere on the highway,” Monks says. “My dad picked him up, and my uncle just sort of took on this persona of [a] drifter.”

Even when his past is painful, Monks can find the humor. When his English teacher-turned-radiologist dad and secretary-turned-social-worker mom divorced, they consulted Monks.

“They said, ‘We both love you, and we’re not going to take it personally,’” he says. “‘We just want to have your opinion about who you’d like to live with most of the time.’”

Monks chose his mom, and now, he jokes with her about his first thoughts: “I remember thinking, ‘My mom is the one with the color television,’” he says.

At school, Monks’ own comedic gene began to express itself.

“I was sort of like a ham,” Monks says. “I wasn’t like a class clown, but I was funny in high school.”

Around graduation time, Monks realized that he wasn’t interested in going to college.

“I was smart,” he says, “but I didn’t have the self-drive to be a good student.”

All his friends, however, were interested in going to college. Not wanting to be left out, Monks began Emerson in the fall of 1987, only to drop out in his first semester. He later returned to school to get bachelor’s and master’s degrees from the University of Wisconsin-Madison and Lesley University in 1996 and 1998, respectively, and began working as an elementary school teacher.

In between those degrees, through a mutual friend, Monks met his wife while she was attending Harvard University. They married in 1997, and in 2001, when they had their first son, Monks stopped teaching. In early 2002, he started writing “Utter Wonder,” a blog that chronicled the life of a bored stay-at-home dad, a fictionalized version of himself.

“I had written a lot [of short stories] at UW-Madison, so my return to writing was initially more of an extension of that,” Monks says. “It wasn’t until writing my blog I started writing comedy more.”

By the time his second son was born in 2003, Monks had landed his first clip on McSweeney’s Internet Tendency.

In 2005, he decided to return to teaching. He recalls an interview where a search committee member took umbrage with a series on his blog featuring un-mailed letters to Star Jones, a former co-host of The View.

“It was the early days of the internet,” he says. “The woman took it literally.”

In order to accept the job offer, Monks learned, he would have to delete his blog. He withdrew from the search.

“It was less about not taking down my blog and more about realizing that I loved writing more than I loved teaching,” Monks says.

After a conversation, Monks and his wife agreed that he would spend a year focusing on his writing.

“Literally the next day, we were at my mother’s house when I received the email,” Monks says of the serendipitous note from a former editor at Vintage/Knopf/Random House. “That was the little ‘umph’ that I needed to pursue this new career.”

The editor had read “Utter Wonder” and “I’m Stuck in Rehab with Pat O’Brien,” a parody blog that Monks originally wrote anonymously. (He later identified himself as the author once O’Brien left rehab.)

The editor asked if he’d thought about writing a book or a humorous collection of essays.

“Nothing came out of it…but the fact that I had interest from her helped me land an agent and my first and only book,” he says.

That book came Monks’ way a few years later via John Warner, the former editor of McSweeney’s Internet Tendency. Warner had published at least a dozen of Monks’ pieces in 2006, and the next year, he asked Monks if he had any book ideas for Tow Books, Warner’s resurrection of a family publishing house. With the help of his agent, Monks signed a contract for The Ultimate Game Guide to Your Life: Or, The Video Game As Existential Metaphor.

In mid-2007, Warner, who had stayed in contact with Monks, had another question: Would he be interested in interviewing to replace Warner?

Yes, he would.

After an interview with McSweeney’s founder, Dave Eggers, Monks took over the site, working at home from Arlington, Massachusetts.

Though he’s largely been focused on growing the site, he’s found time for personal works. He finished a memoir in 2015 but tabled the project.

“Part of me thinks it’s too personal to share with the world,” he says of the tome on “parenting, gracelessly becoming middle-aged, and my eldest son’s last season of Little League baseball.”

Perhaps sharing would combat what he believes is a common misconception about him.

“People think that I’m some hipster in a cafe, and I’m not that person,” Monks says; rather, he’s a grown man who enjoys spending time with his wife and 17- and 15-year-old boys.

When Monks took the job at 37, he found it hard to envision his life at 50, let alone if he’d still be a McSweeney’s humor editor.

Welp, 50 is two years away. What does Monks see at 60?

“I feel like I’m good at what I do. I feel like it’s the right audience. It’s fun selecting pieces that I think will make other people laugh,” Monks says.

“As long as someone can send something in about a fidget spinner and I know what [a fidget spinner] is, I’ll keep doing it.”

The women behind The Belladonna

From left: Fiona Taylor, Caitlin Kunkel, Brooke Preston, Carrie Wittmer

Twenty years ago, four women burst onto screen in an HBO television comedy that unabashedly explored all things related to the “S” word.

Today, four women (including one named Carrie) have burst onto the internet with a new comedy website about the other “S” word: satire.

The Belladonna is a satirical women’s site founded and edited by writers Caitlin Kunkel, Brooke Preston, Fiona Taylor, and Carrie Wittmer.

Throughout 2016, Wittmer had posted in a Facebook group about the need for a comedy and satirical site by women. After the election, her posts went from comments to calls for action: Who wanted to start a website?

Kunkel and Taylor responded.

“I think the election probably had a lot to do with it because we all wanted to write, like, fire satire about the political climate,” Wittmer says. “So I think it’s not a coincidence that that’s kind of when we started to do this.”

Kunkel suggested inviting Preston, a former student in her online satire class at Second City. Preston accepted, and season one of The Belladonna began.

During our interview, the foursome realized their similarities go beyond their known satirical interests and the odd coincidence that Taylor and Preston’s daughters are both named Arden. For starters, they grew up with only female siblings.

“I think not having a brother helped me be a little more confident,” Wittmer says.

Kunkel also attended an all-girls high school because her father wanted her to see women in leadership positions.

“When I got to college, I was so used to speaking up all the time,” says Kunkel. “I love, love nothing more than to call out hypocrisy.”

As children, the editors stayed home on weekends to transcribe episodes of television shows and podcasts. Among their archives are Rosie O’Donnell’s VH1 shows, The X-Files, The OC, and Harry Potter podcasts.

“What we’re trying to say is we were all really cool,” Preston jokes.

None of these cool girls set out to make a career in comedy. Kunkel, a Fulbright Scholar who taught English to Indonesian high schoolers for a year, did her undergrad at Johns Hopkins and then finished an MFA in writing for the screen and stage at Northwestern. About a month after finishing her degree, she says, her “brain cracked” and she realized that she wanted to write comedy.

“Instead of coming into someone’s face with dramatic writing, I hit them from the side with satirical writing,” she says.

Now, Kunkel is throwing comedic blows full time, teaching online classes for Second City and writing for a public radio show.

Preston went to Ohio University in Athens as a music major, which she “semi-enjoyed” until deciding to change her major just before graduation. After studying music for years, Preston says doing her senior thesis on the comedy of the Chris Farley and David Spade film Tommy Boy “felt like I was getting away with something.” She’s now an instructor for the satire course that Kunkel created.

Taylor, the self-proclaimed Gen X “senior citizen of the group,” got undergrad and grad degrees in English lit at the University of Florida and the University of Miami, with the intent to be an English professor, until she had two realizations.

First, the “top people coming out of amazing programs [were] getting jobs in the Black Hills of North Dakota,” where she had no desire to be, and second, “academia [is] as cutthroat as the corporate world.” She began working in e-commerce and currently is a copywriter and digital strategy consultant in Florida.

Wittmer, who graduated from Savannah College of Art and Design in 2011 with a degree in creative writing, spent around 18 months at home after graduation, clawing for one of the few jobs that hadn’t evaporated during the recession. Her parents gave her some money and told her to go to New York. Once there, she began freelancing and working as a nanny but was essentially unemployed when they founded The Belladonna.

“[It] made me feel like I had purpose,” Wittmer says. She’s now a full-time entertainment writer (“with health insurance”) for Business Insider.

One of the ways The Belladonna tries to help other women writers find their purpose is by accepting submissions from new writers. For the editors, this has been one of the most rewarding aspects. Kunkel is inspired when a woman who has never written comedy says that The Belladonna inspired her to try.

“[They say] ‘I feel like I’m not going to get made fun of, and I’m not going to feel bad if this doesn’t get in,’” Kunkel says. “That, to me, is really cool.”

Preston believes The Belladonna empowers women by making rejection a positive experience. They offer constructive criticism, which might include referrals to other sites.

“We’ve seen pieces that we’ve rejected go on McSweeney’s or Robot Butt,” Wittmer says.

McSweeney’s Internet Tendency editor Christopher Monks inspired their approach.

“His rejections are always kind and respectful, and it starts to feel like he does remember your work,” Wittmer says.

The Belladonna also features work from established writers.

“[The] mix helps,” Taylor says. “It not only grows our audience…but…I think it gives such a unique flavor to the site.”

That flavor has attracted 24,000 followers across their social media platforms and a shout-out from Monks in an interview with Splitsider. Recently, the foursome sold a book, New Erotica for Feminists, based off of their viral McSweeney’s post of the same name.

Unlike other sites featured in this piece, The Belladonna’s contributors must be women or non-binary people, but readers of all gender identities are welcome.

“[The site] has things everybody can appreciate – not just ‘women’s issues,’” Preston says.

Still, those issues are a priority. The site hosts awareness events like the Belladonna Ballyhoo, when it published 12 pieces on sexual harassment in 12 hours, and the women are planning quarterly fundraisers for nonprofits that help women and girls.

It seems their success stems from their commitment to supporting each other and the female writing community, efforts that have also boosted the editors’ confidence.

“We think we’re funny; other people think we’re funny and our taste is funny,” Taylor says. “That’s affirming to have that happen.”

Brian Boone, Splitsider

Brian BooneBefore “fake news” was a popular phrase, Oregon native Brian Boone dabbled in fake facts – specifically by way of his work on Fake Facts: Really Unbelievable…Because They’re Not Real, a book in the Uncle John’s Bathroom Reader series.

Boone began working at the Bathroom Readers’ Institute, the series’ publisher, in 2003, a year after graduating from the University of Oregon. He says BRI published one 500- to 600-page book a year on a variety of topics and shorter books on single subjects, like his Fake Facts trivia book.

“That was a satisfying place to be [in] because I could still write with personality and humor,” Boone says.

Boone had been developing his writing style since he was a kid in Portland. His dad, a sales manager for companies in the food and beverage industry, and his mom, a travel agent and then church employee, were supportive of his efforts in comedy and writing.

“I’m not sure if it was good or not,” Boone says. “They told me that it was.”

In high school, he wrote a humor column as the editor of his newspaper and penned sketches that were performed during the morning announcements.

“That feels like the first real comedy I did,” he says. “People laugh, and that is intoxicating and addictive.”

But it was an addiction that the University of Oregon theater and journalism major didn’t think could be satiated.

“This was, like, early 2000s, and there wasn’t really internet comedy writing,” he says, noting a writer’s main choices were deciding between Los Angeles or New York. Instead, he applied for a variety of theater and writing jobs, including BRI.

“It was like being in a newsroom,” Boone says of his 9-to-5 job. “[In the morning] we’d pitch it, write it, and move on to the next one…eight months later, we’d have a book and publish it.”

Even though he enjoyed the work, his eyes began to wander.

“I think I just started to kind of feel – not creatively unfulfilled – but I thought I could do more,” he says.

He started writing and publishing his sketch comedy on a blog and occasionally wrote one-act plays that would get produced.

Around 2008, Boone’s wife suggested that he write a humorous music trivia book.

His proposal landed an agent who secured a deal with Penguin for I Love Rock n’ Roll (Except When I Hate It), which came out in 2011.

Acquiring a taste for working on his own, he began applying to various sites and ultimately worked at The Onion, Someecards, and ClickHole but credits one of his next moves to writer, author, and Vanity Fair contributing editor Mike Sacks.

“Everybody who is anybody in comedy writing and internet writing owes a debt to that guy,” Boone says.

After reading an article about Sacks on Splitsider that year, Boone pitched himself as a writer for Sacks’ imprint, Bulldog Front. Sacks didn’t need authors, but he was looking for writers for “Not a Blog,” a daily comedy website that he ran on Adult Swim.

When the blog ended because of a clash between content and the parent company’s rules, Sacks recommended Boone to Funny or Die.

“He could write humor for print which is a very specific skill set,” Sacks tells me in an email. “And he’s a nice guy, easy to deal with. That counts for a lot.”

At Funny or Die, Boone had the freedom to write comedy “whenever the idea struck me.”

“That kind of started the thing [where] I’d try to write one or two comedy articles a week.”

Boone began publishing more, including on Splitsider, a site he read voraciously because it felt like a home for “comedy nerds.”

One day in early 2013, he noticed that the humor section had been dark for a couple weeks, so he sent an email to the humor editor at the time, Rebecca O’Neal, inquiring why.

O’Neal, who’d been the section’s editor for a year, said that she’d started to focus more on live comedy and performance, and her editor had asked her to find a replacement.

When Boone learned about her time constraints, he asked to do the job, unaware that he was already on O’Neal’s list of potential successors.

“I liked the humor pieces he submitted when I was editing Splitsider,” O’Neal says. “[I] picked him because he had a good sensibility and loved print humor.”

Those two skills likely helped ease Boone’s transition into his editorial duties.

“I had to base it on my predecessor’s tastes – which is fine because she had excellent taste and [had] established the formats and kind of articles that worked – while also kind of giving a nod to the future and trying to find new forms and new people,” he says.

As he worked for these other publications, Boone kept his full-time job at Bathroom Reader Institute. Then, in 2016, BRI converted its full-time staff to freelance, sending him into “sheer panic.”

“But things kind of came together because I’d been dabbling in freelance on a lot of different websites and writing some books on the side for other publishers,” Boone says.

Soon, his side-work became his main work, and Boone has written and sold 16 books over the last decade. He also still writes for BRI while working out of his Ashland home.

After he helps his writer wife, Megan, get their 11-year-old son ready for the bus, Boone takes care of the dog and is at his desk around 7 a.m.

“I [usually] have one long article due at noon and three short articles due by 9, and I start plugging away and don’t come up for air,” he says.

He sifts through around 70 potential Splitsider pieces weekly.

“I try to take a little break around noon or 1 and go back to work until probably 4. Then I spend some time with my family, then write [from] 10 p.m. to 1 a.m.”

He’s never been big on sleep, and it seems the disregard might be paying off. Boone has three books dropping in 2018.

From the outside, one might look at his life – editor, author of 16 books and counting, prolific freelancer, happily married man with a wife and 11-year-old-son – and conclude that he’s, in a sense, arrived.

“I’m so tremendously lucky that I get to do them all, [but] there’s so many other things out there that I want to do,” he says. “There’s always another book to write. I like trying and going for it and seeing what happens. I’m pleased with what’s happened for me. Very much so.”

Marty Dundics, Weekly Humorist

Marty DundicsIt was a Dan Quayle joke that did it.

Weekly Humorist Editor Marty Dundics recalls the editorial cartoon that he drew in fifth grade. In it, two men speculate the reason an angry mob has gathered. As a black limo drives by, one says, “Oh, Dan Quayle must be back in town.”

“I was in fifth grade, and the teachers didn’t think political cartoons were appropriate for an elementary school newsletter,” says Dundics.

Before our interview, he’d stumbled upon the drawing in his parents’ Maryland basement.

“I’ve always been kind of a smart ass,” he says. “I would be a smart ass verbally, but I found being a smart ass in cartoons was fun. It was fun to be in print. I really got a thrill out of that.”

After graduating high school, where he was the art director of the newspaper, he attended Syracuse University to study illustration and worked part-time as the morning show host at the student-owned and -operated radio station, WJPZ-FM.

“I knew I wanted to do something creative, and I knew I wanted to do something with comedy,” he says.

Despite not having a specific plan, he’d always had a dream: to work at Late Show with David Letterman. As a kid, he had marked the Ed Sullivan Theater on a map of Manhattan that hung on his bedroom door. At night, he covertly stayed up late to watch Letterman, who, along with Steve Martin and Bill Murray, shaped Dundics’ sense of humor.

After college, he moved to New York City and settled in a Park Slope apartment in 2002. He’d only been in New York for two months when he “completely fell into” a job at Late Show. While he shuffled his large black art portfolios between magazine offices in Midtown, a woman outside the Ed Sullivan Theater offered him tickets for that night’s Letterman show.

Dundics declined but later shared the incident with a friend who, unbeknownst to him, worked for the show. Shortly thereafter, his friend left for another job and got Dundics an interview to become her replacement. Over the next three and a half years at Late Show, Dundics met many of his contemporary comedy colleagues, including a woman who worked at National Lampoon.

That connection led Dundics to freelance work as an illustrator there, and he went on on to become creative director and editor-in-chief until National Lampoon was sold in mid-2017.

After the sale, Dundics, who’d been running solo for two and a half years, launched the Weekly Humorist in August 2017, setting up headquarters in a WeWork office on Wall Street. The office space shared with fellow creatives and entrepreneurs has created an encouraging community, especially helpful for Dundics since Weekly Humorist’s managing editor, writer and cartoonist Kit Lively, lives halfway across the country. Lively works from Texas and contributed to National Lampoon regularly for Dundics.

After NL folded, their friendship turned into a new business relationship when Dundics asked Lively to come on board with the Weekly Humorist, which is a venture of Humorist Media, a development company co-founded by Dundics and former Comedy Central executive Lou Wallach.

The relationships that Dundics has made through the years have been instrumental in the early success of Weekly Humorist. Award-winning cartoonist and writer Bob Eckstein submitted work to Dundics at National Lampoon and now contributes to Weekly Humorist. 

“He is extremely generous and very respectful of me,” says Eckstein. “I think it’s an excellent working relationship.”

Lively, who hasn’t met Dundics offline, is betting on that relationship, too.

“I’m really excited and hopeful about the possibilities from Humorist Media,” Lively says. “I think we’ve got some really good ideas that we’re already working on that could make good programs.”

Dundics charted those ideas for possible revenue streams on the dry erase walls in his WeWork office.

“Over the last few months, all of them have happened. They aren’t making the money that I would want, but all of them are firing a little bit,” he says. “It’s all of the stuff that I wanted to do at National Lampoon but didn’t get to.”

At Humorist Media, he hopes to create television pitches to sell to Netflix or Comedy Central.

“I want to be a good content creator,” Dundics says.

He doesn’t see the small staff size as a hindrance.

“If I’m making all the decisions, things can move fast. I can implement something and launch it tomorrow,” he says. “And I’ve got nothing but time right now. I have to make it work, so that’s what I’m doing.”

Emma Allen, The New Yorker

Emma AllenWhen New Yorker humor editor Emma Allen was around 6 years old, her goldfish got the ich, or white spot disease.

Allen recalls that her mother, then a corporate lawyer, left a multimillion dollar merger meeting to deal with a distraught little girl with a dead fish.

At home, her mom placed the fish in a box and tried to explain death.

“My immediate response was ‘Can we eat it?’” Allen says.

Now, the only pet Allen has is CiCi, a horse she says has a “similarly rude personality” to her own and lives at her mom’s and stepdad’s Long Island home. Riding CiCi – but “not very well” – is one of the things you might find Allen doing when she’s not in her office sorting through potential humor pieces for The New Yorker’s online humor column “Daily Shouts” or choosing cartoons for the print mag or online feature “The Daily Cartoon.”

The 29-year-old Manhattan native has been working for The New Yorker since spring 2017, succeeding longtime cartoon editor Bob Mankoff when he left the magazine.

“I had been growing in this humor editing role [of ‘Daily Shouts’], which had been evolving and expanding under me, and then [New Yorker editor] David [Remnick] offered me the job that … was this even bigger pan-humor role with hopes that I would expand what cartoons in the mag were and what comics in the mag and online were,” Allen says.

You might think that Allen had been laser-focused on a 10-year plan to be an editor at major mag by the time she was 30. You would be wrong.

“I wanted to be a lobster fisherman,” Allen says of her high school career aspirations. “I read this early novel by Elizabeth Gilbert [about lobster fishermen], and it just seemed like this really fun, adventurous, outdoorsy life.”

One of her high school teachers thwarted the plan when he asked if she’d ever touched a lobster.

She had not.

Allen’s other career goals included novelist and medievalist historian.

“I read a lot of fantasy books that took place in a sort of mangled medieval-ish world, so I somehow conflated in my mind that studying medieval history was like studying magic and dragons, which, of course, it’s not,” she says. “It’s like studying feudalism and the plague, which is much more boring.”

She might not be seeking out new comedic voices for The New Yorker today if her parents hadn’t let her find her own.

“They both encouraged me to follow my interests and didn’t put a huge amount of pressure on me to have a plan, which, luckily in my case, worked out,” she says. Even though they liked their jobs, they didn’t push her to follow their paths into law or finance.

“They [also] saw how bad at math I was, so they knew that was a lost cause,” she says.

After graduating from an all-girls private school in New York City that she had attended since kindergarten, Allen went to Yale…‘cause, well, Gilmore Girls.

She pursued a major in English but also took a number of art classes. By graduation time, she realized that she had enough classes to do a double major in studio art.

“Thank god I ended up with a career where much funnier people could make me laugh and draw much better than I did,” she says.

Today, Allen spends some of her free time reading memoirs and graphic novels.

“It benefits me to have a much more comprehensive knowledge of the stuff that’s out there and who’s making what work,” Allen says. “But it’s been super fun. I’ve read some stuff in that genre before, but now that’s all I want to do.”

Sometimes it seems like the work never stops: “[It’s] a never-ending task to advocate for the writers and contributors that you care about,” she says, “and to make sure that you’re finding the most interesting new voices.”

As our conversation comes to an end, I note having a coveted editorial job at a revered magazine is something many people chase for decades.

“Now that you have it,” I start, “do you feel like you have – ”

“Nowhere to go but down?” she interjects, catching me off guard.

“I feel like I am incredibly lucky to be in the position that I’m in, despite also having worked very hard for it,” she continues. “But it’s not like I’ve arrived and get to recline and just survey my kingdom. I now have to really put in the work and prove that I’m the best person for this job.”

Steve DiMatteo and Bronson Arcuri, Robot Butt

Steve DiMatteo and Bronson ArcuriSteve and Bronson. Bronson and Steve. Two men. One Robot Butt.

Born two months apart in 1988 in Painsville, Ohio, Steve DiMatteo and Bronson Arcuri wouldn’t meet until middle school, when they would begin a friendship that would take them from filming sketch comedy in the front yard to sparring with McDonald’s on Twitter decades later.

Arcuri and DiMatteo grew up in blue-collar homes. DiMatteo’s dad worked his way up company ranks at a beer distributor, and Arcuri’s dad worked at a factory named Lincoln Electric. Both had stay-at-home moms. Around the eighth grade, Bronson and Arcuri formed No Dice Films with another friend. Both say their families were supportive of their creative endeavors.

“As long as I was enjoying what I was doing, they were happy with it,” DiMatteo says, even though he believes their on-location shoots were “no doubt embarrassing for them.”

Like other editors I interviewed, Arcuri says there was “never a time when we were like, ‘we’re going to do comedy professionally.’” Arcuri started Ohio University as an aviation major (a mistake, he quickly offers), and DiMatteo began in sports management. By graduation time, they’d found their way to majoring in video production and creative writing, respectively. DiMatteo now works as the director of an internet marketing company. Arcuri is a videographer for NPR.

In 2014, their friendship birthed more than their knack for finishing each other’s sentences. They started Robot Butt, a comedy website that would be an outlet for other types of comedy writing they were doing.

“What I do like about our site is that everything is always a mishmash, so that at any given time you could come to the site and read just completely three or four different things,” DiMatteo says.

The site is designed with two sections that are meant to help readers separate the serious (but maybe funny) content from the completely fake.

“I put enough faith into people reading on the site to just know, ‘oh, this is a fake news story’ or ‘this is just a funny commentary,’” DiMatteo says.

One example of Robot Butt’s unique commentary is the October 2017 post “Okay, Willy Wonka Might Not Have Eaten Them, But He Definitely Killed Those Kids” by Linton Lewis, who published it under the pseudonym David Morgan.

The angle of whether Wonka ate the kids is “inherently funny,” DiMatteo says and made it worthy of posting.

But the argument Lewis makes – that Wonka had nefariously pre-picked the ticket winners and had never intended for them to return home nor stay alive – raises points sound and intriguing enough to warrant an immediate search for the film on streaming video.

“Even when we write things that have a serious tone, we try to put jokes in there of some kind, whether it’s, like, a dig at someone or something [or] subject we’re writing about,” DiMatteo says.

The editors attribute the site’s tone to a group of guys who have been instrumental in Robot Butt since the beginning

“Between Bronson and I, there’s like five or six other guys, where I’m not exaggerating, like every single day, we’re pitching jokes to each other,” DiMatteo says. “We’re working out ideas. We’re trying to develop new things to write about or maybe new avenues to get into.”

Because of that effort, Robot Butt soon met its goal to post new content every day, Arcuri says.

“Now people are submitting things to us, and every day that we get a submission, it blows my mind,” Arcuri says.

People are not only submitting, they’re also searching for Robot Butt, albeit incidentally. Each month, they run “How You Found Robot Butt,” a series that highlights the search terms that led people to the site.

“You’d be shocked how many people have typed in a different way of saying ‘how do I sell my soul to the devil,’” DiMatteo says. (So far he’s tracked at least 50 variations of the query.)

“It’s a legitimate concern that there are this many people trying to sell their soul,” he says. “I hope I’m putting across how gravely concerned I am.”

Now for a concern we need to address. It’s the Robot Butt in the room.

“[The name] is a topic of much debate,” says DiMatteo, who pitched it in a brainstorming session. “We laughed about it [and] one day [were] like, ‘that’s really funny. We should do that.’”

A graphic designer friend drew a logo that they thought was “good and hilarious,” and they ran with it.

“I do remember calling to register the domain and the guy on the phone laughing at the domain,” Arcuri says. “I felt pretty good about that.”

“We never thought a few years ahead, like, ‘would that hurt us at any point, having a site called Robot Butt? Would that hurt us trying to get a legitimate interview?’” DiMatteo says. “Luckily, the answer to that is no.”

In 2015, Robot Butt broke the story that Chris Rock was hosting the 2016 Oscars. They got the tip from one of DiMatteo’s friends who worked at the Academy of Motion Picture Arts and Sciences and gave permission to publish it.

“I tweeted it at the editor of Variety – and god bless this man – he said that we were the first site to report it, and then it just blew up from there,” DiMatteo says.

“And so we had a really fun month of people who write for the LA Times and Hollywood Reporter saying, ‘What is Robot Butt and why did they break the story and not us?’”

“The fact that these prestigious publications had to put Robot Butt in their copy was the best prank that we ever played,” Bronson says.

Another unexpected blitz of publicity happened when Robot Butt found itself trading barbs with the McDonald’s Twitter account. The exchange began over a satirical post titled “McDonald’s Won’t Deny McRib Is Made of People.”

“[They] were responding but like with meat puns,” DiMatteo says. “Rather than ignoring us, they were literally making it sound like ‘wink-wink, maybe it is.’”

When they’re not beefing with hamburger joints (pun intended), DiMatteo and Arcuri are trying to grow their “labor of love” into a real, live, self-sustaining piece of virtual real estate.

To get there, they’re focusing on the positive.

“I don’t have any negative things people have said about Robot Butt, and if they did, they can come find me and we’ll fight,” DiMatteo says. “That’s a promise.”


—Keysha Whitaker’s work has appeared in The Writer, the New York Times, and The New Yorker. She has an MFA from The New School.