He’s 27. He has a beard. Yet this KC man has a hit show playing an 11-year-old kid
All the people currently compelled to work from home can appreciate what Trey Kennedy has accomplished.
From his house in suburban Kansas City, the comedian cranks out short videos that have earned 100 million views. And, yes, this is his day job.
“I’ve been making these for seven years on different online platforms, and for the first few years it felt too good to be true – like, surely this will end,” Kennedy says. “For whatever reason, I have a knack for finding a way to relate to a large number of people and make them laugh.”
He’s gained 4 million followers on Facebook and another 4 million through TikTok and Instagram. He’s also acquired a celebrity fan base that includes Chiefs tight end Travis Kelce, NBA All-Star Kyrie Irving and “The Office” actress Jenna Fischer.
Now he’s turned his most popular character into a KC-based web series that he hopes to adapt for television.
“Middle School Maddox” finds the 27-year-old Kennedy portraying its titular hero: a gangly doofus whose life revolves around playing video games and not completing the chores his parents ask him to do.
“It’s a relatable, family-friendly slapstick series played by a grown man with a beard,” Kennedy says. And no it’s not animated, it’s live-action.
The comedian is so oddly convincing as the petulant 11 1/2-year-old that audiences can immediately suspend their disbelief at the preposterous casting. Since it debuted on YouTube in March, the series has drawn 4 million views.
“Maddox is just an extension of how I behaved at that age. So what started as a little funny sketch turned into an actual character with a name and a series,” he says. “I’ve always thought that part of why Maddox works is because of the ridiculousness of it all. Not only am I clearly an adult, but I don’t even care to shave off my beard. But the braces are a big help.”
Kennedy acknowledges he shares some of the same flair for drama as his alter ego.
“My fiancée jokes that when I don’t want to do something, she’ll say, ‘That was a little bit of Maddox right there,’” he concedes.
Finding his audience
Raised a strong Southern Baptist in a suburb of Oklahoma City, Kennedy originally was more interested in pursuing a career in business than comedy. He attended Oklahoma State University, eventually earning an MBA. While in college, his short clips on the now-defunct Vine platform began racking up absurd amounts of views.
After all his friends moved away to various cities to be responsible adults, Kennedy realized he didn’t want to stay in the same vicinity where he’d grown up.
“I was nearing the end of college and at a crossroads. I was applying for jobs when I was starting to make some income online with social media. I needed a fresh scene. And I had a couple of my good friends living in Kansas City,” he says.
So he moved to KC in 2016, instantly putting his business training to work promoting his humorous material.
“The tools throughout college and graduate school certainly helped come into play when trying to navigate that,” he says.
“I’m fortunate to where my content is family-friendly and PG-rated, so that makes me super brand-friendly. I have a great opportunity money-wise to do sponsor videos for Fortune 500 companies. Alongside that, when you watch a YouTube video, and there’s a five-second ad before it, I get a tiny percentage of money. That happens across different platforms.”
Multiple platforms. Millions of times.
Last summer, he decided to develop his most popular character into a four-episode web series. He recruited director Sam Findlay, whom he’d initially found on Instagram while looking for help with a Kickstarter video a couple years prior.
“Trey has a really great understanding of his audience and the content his audience loves,” says Findlay, who co-writes “Maddox” with Kennedy and Jake Triplett.
“If you look at our audience, it’s a lot of women, specifically moms in their 20s, 30s and 40s. They like it because it’s a playful jab at how their kids act. They don’t feel like they’re alone. This is definitely a universal thing that other people are experiencing.”
Amusingly, neither Findlay nor Kennedy have kids of their own.
As for why the comedian connects so well with his viewers, the director cites several reasons.
“I would say acting-wise, Trey is incredibly good with his face. He’s so skilled at imitating. When he wants to emphasize or even exaggerate an expression or emotion, he does a great job of that. Writing-wise, he understands how to make jokes relatable to people,” says Findlay, a graduate of Shawnee Mission Northwest High School and the University of Kansas Film and Media Studies program.
Comedy tour on the way
Although Findlay relocated to Los Angeles last year to be closer to the industry, Kennedy remains based in Kansas City with no plans of heading to Hollywood.
“I made a decision that I don’t have a desire to be an actor,” Kennedy says. “I want to do ‘Middle School Maddox’ to where I’m making it and creating it. I’m not as interested in playing a role someone else wrote and spending two months on that.”
However, Kennedy was more than happy to showcase his skills around the country. At least that was the plan in March when he launched a 21-city comedy tour that sold out in advance. Sorry, no stops in KC for now.
“While we were out on the road, we had to pull the plug when everything was falling apart. That was obviously a bummer. Now I’m going back to what I have been doing for a few years, which is trying to make videos in the comfort of my own home,” he says.
The tour was crafted as a mix of stand-up, clips and live music. Maddox didn’t make an appearance per se, but Kennedy says he gave some nods to the character.
“To be frank, the tour was going to be potentially life-changing for me. I didn’t want to be a ‘YouTuber’ the rest of my life. I was really excited to be a full-fledged comedian and go tour the country,” he says.
Fortunately, he’s rescheduled for an already sold-out tour running October through December. Until then, the plan is to find a way to bring “Middle School Maddox” to a bigger audience.
“We’re putting together a visual pitch deck to show some networks and online streaming platforms,” Findlay says.
The 31-year-old filmmaker is hoping to leverage having millions of views for the first season. But he admits the PG-nature of the project could either work for them or against them.
“We weren’t sure if the tone was going to be for kids or adults. But we think we found a nice little balance. Like with Pixar, kids love it and adults love it,” Findlay says. “For us, it’s nostalgic, looking back on what we were like as kids and how we saw our relationship with our parents.”
Kennedy adds, “My comedy is informed by experiences, and a lot of people have my similar experience of growing up in Middle America with a conservative, close-knit family.”
“I funded Season 1 because I believed in it. We would love to have four or five times the money to do Season 2 bigger and better, and to really expand Maddox’s suburban world.”
Jon Niccum is a filmmaker, freelance writer and author of “The Worst Gig: From Psycho Fans to Stage Riots, Famous Musicians Tell All.”
This story was originally published May 31, 2020 at 5:00 AM with the headline "He’s 27. He has a beard. Yet this KC man has a hit show playing an 11-year-old kid."