by Anne Marie Kirsten

Driving east on Danforth Avenue early one evening in October, headed toward Comedy Bar, I could feel the last rivulets of summer dripping away. Sidewalks were crowded, and as shops and cafes decanted, restaurants filled up. Misjudging the location, I didn’t realize how far down one of Toronto’s busiest roads I’d be going. By the time I parked, the hand-holding passersby near Pape Avenue had slowly morphed into small groups of unhoused people near Main Street, huddled, sharing blankets. It felt like I’d travelled through multiple cities all on one street. Such is the magic of the Danforth.

When I’d booked tickets to see American comedian, Deric Cahill, and pitched it to my besties as an easy-breezy moms’ night out, a tiny part of me knew, come the evening of, I might feel a twinge of regret. Putting on hard pants and leaving the comfort of home isn’t usually at the top of my agenda, but I pushed through and was richly rewarded.

I discovered Cahill like most of his fans, scrolling my phone before bedtime. The 36-year-old comic is famous for his F*&! This House series of videos, where he attempts to repair a variety of broken things in and around his home in Dallas, Texas. Picture a witty, bearded, cussing Tim “The Toolman” Taylor, but shorter. His content isn’t only about him doing battle with his algae-coloured pool, or cursing his five-foot-seven frame as he attempts to clear his eaves. He is also a husband, a father to three kids, and a serial entrepreneur. Like one of his over two million social media followers, you might be lured in by the hilarity of his DIY videos, but you’ll keep coming back for his Karen-shaming ripostes to comments, acerbic-yet-heartfelt notes on parenting, and the sheer relatability of him as a human being.

My mini mom brigade and I arrived early enough to avoid the front row at the first of Cahill’s two sold-out shows that evening. The atmosphere was dark and cozy. Small enough to feel intimate, but large enough to warrant Cahill’s growing Toronto following. Comedy Bar is self-billed as “Canada’s official comedy hub,” where, “every Canadian comedian has had a beer […] and every visiting international comedian has stopped by to see what all the hype is about.”

Image credits: Jan Jennings

When the warm-up acts made way for Cahill, the crowd was ready to see what they came for, and he did not disappoint. He opened by talking about how polite people seemed in Toronto, and that he had an uncle that once played for the Toronto Maple Leafs. He then moved to drawing our attention to his red-and-white cap, used as a decoy to MAGA supporters in his Republican-leaning US state. Cahill hit the topics he’s known for: frustrations with raising a teenager; the closure of his chocolate company, Wicked Bold; and his parents. Oh, and he riffed on negotiations he’d had with a person requesting to purchase a pair of his used underwear.

Cahill is open on his platforms about his mother and father being substance abusers, and that they both died when he was about 25 years old. He makes no bones about what terrible parents they were. He jokes about having their remains delivered to him in cardboard boxes and, not knowing what to do with them, deciding to sprinkle them on stops on his tour. I was so struck by this as an audience member. His commentary didn’t land flat. It wasn’t delivered for shock value, and it never felt gimmicky or pathetic. It’s his truth, conveyed in a matter-of-fact way. Not as a jovial prop, but as something that sets the scene.

In our interview, I immediately realize that, in the trifecta of my interactions with him and his material (Instagram, live show, personal interview), he is who he says he is. There’s no artifice—he’s relaxed, open, intelligent, and generous. What you see is what you get. And it’s hilarious.

We talk about where his comedic journey began, and he tells me that he first realized he was funny in seventh grade as the talent show MC at his school near Boston, Massachusetts, where he grew up. He then did theatre arts in high school. “Being on stage felt like being home,” he says. After high school, he did a variety of jobs like door-to-door sales and working as a restaurant server. When he moved to Florida, he took a job as a waiter in a restaurant called Off The Hook that also hosted stand-up. One night, he gave it a shot. He explains that the first time was really terrible but so very exciting, so he persevered. “Comedy is a strange career, if you can call it that. There’s no ladder, there are no steps, there’s no job security.”

Despite his talent and ability to do crowd work, after a few years he gave up on pursuing it, even as a side gig, and went back to corporate America in 2016, which he detested. In 2019, he and his wife, Brooklynn, were inspired to start a chocolate company called Wicked Bold. It grew quickly, and they successfully obtained a contract with Walmart. But if the start-up world can be likened to a symphony, and one instrument is out of tune, the whole orchestra can collapse. And with one supply chain delay, such was the fate of their company. Wicked Bold folded this past fall.

Given his experience, I ask him whether, in this economy of record global inflation, he’d recommend that someone go into business for themselves. He answers with a resounding yes. “People are so afraid to be failures. But failure is a gift,” he says. “Be a scrappy squirrel!”

“I was an adult without parents. I don’t want the same for my kids. My parenting, in a lot of ways, is a rejection of how I was parented.”

When we talk about what comedy gives him, he explains that it’s really the other way around. At that low point a few years ago when he wasn’t getting gigs, he told his wife he was done for good. But shortly after, the universe spoke and he received a call from a club asking to book him, and he’s never looked back: “Comedy picked me.”

Thinking of his parents, I mention the realities of life I witnessed just outside the doors of Comedy Bar. Food insecurity and opioid deaths are increasing in both of our countries. This leads to my question about his own upbringing and how it informs his parenting style—hair-pulling exasperation mixed with a dose of loving understanding—and whether his comedy is healing for him.

“I was an adult without parents. I don’t want the same for my kids. My parenting, in a lot of ways, is a rejection of how I was parented. I never want them to feel like they can’t come to me because my life is worse off than theirs,” he responds. “I haven’t had a ‘trauma release’ from doing comedy. I write jokes about it that maybe come off more sad than funny. But talking about it is probably healing in some ways that I don’t realize.” He explains that he chose to face things head-on rather than ruminate, but he also knows there’s nothing quick about getting better. He continues: “My favourite quote is one from Steve Jobs. He said, ‘You can’t connect the dots looking forward, only backwards.’”

When he examines the trajectory of his career, he says the difference between himself ten years ago and now is that he writes about things he laughs about, not what other people might find funny. And for anyone looking for success in comedy? “Be yourself,” he advises, “and do it on the internet!”

If there’s one seemingly clear thing about the map of his life so far, it’s that Deric Cahill contains multitudes and he’s only too happy to show it.