Adam Cayton-Holland Reflects on Twenty Years of Comedy Ahead of His Anniversary Show

Adam Cayton-Holland discovered the transformative power of laughter in ninth grade, when he had to deliver a speech to sixty peers.

"You had to give a one-minute speech at the weekly assembly to encourage public-speaking skills," Cayton-Holland recalls. "The private school I attended had big Future Leaders of America vibes, and everybody lived in fear of that moment. I remember I used to watch David Letterman every night, and I loved the top-ten lists. When it was my turn to speak in class, I did a list that I wrote, and everybody was just blown away — it just crushed."

His top-ten list humorously considered what was happening in a massive hole that was dug in the middle of campus during a construction project. Despite not being the most popular kid at school, Cayton-Holland was suddenly inundated with positive feedback from his classmates after his comedy routine. "Even though everything returned to normal the next day, that experience was very important to me," he says. "I was like, ‘Huh, okay. It feels pretty good to make these people laugh.'"

Decades later, Cayton-Holland is preparing to celebrate twenty years of a career in comedy at Comedy Works on Thursday, April 25. He's become a fixture on the national comedy circuit, appearing on late-night shows such as Conan and @midnight, as well as at comedy festivals, the Kennedy Center and Carnegie Hall — but like most comics, he got his start at local open mics.

The scarcity of stages in the early 2000s — a period when Cayton-Holland was also writing for Westword — didn't deter him; instead, it forced him and his friends to get creative. "We hadn't really earned regular stage time at Comedy Works yet — you have to climb that ladder, rightfully so — but we were super ambitious and hungry for stage time, so we just started doing shows ourselves," he says. "Alt-comedy in the 2000s is a well-documented phenomenon, and I was cognizant of it and wanted to emulate things I had seen or heard about in NYC."

His approach to comedy was also inspired by his love for "really dumb, really smart comedy," including The Simpsons, Seinfeld and Monty Python.

"Behind the best really dumb shows are a bunch of smart writers," Cayton-Holland maintains. "When I was watching standup, I wasn't being exposed to stuff that I considered really smart. I've just always wanted that in my art, probably to the detriment of my career; the dumber you are, the more successful you're going to be. But alas, this is the hill I’m dying on. The New York alt-scene was the first time that I was like, ‘Oh, this shit is so smart!’ I knew that was exactly what I wanted to do — not just dick jokes and blue comedy, but absurd, clever shit."

Inspired by such comedy shows as Eating It! at the Luna Lounge and Invite Them Up at Rififi in Manhattan, he and a handful of local comics founded Los Comicos Super Hilariosos, a comedy collective that began hosting underground shows in 2005 at the Old Curtis Street Bar (now Wide Right) before quickly moving to an art gallery warehouse space called Orange Cat Studios (now the Matchbox). These shows included a mix of standup, sketch comedy, a news segment and live music.

"That's when things really started to pop," recalls Cayton-Holland. "We had an insanely sold-out monthly show [that] national headliners would pop in on; it became a sort of hub for indie, intelligent, outside-of-the-mainstream comedy in Denver."

This DIY attitude inspired Cayton-Holland, Ben Roy and Andrew Orvedahl to create the Grawlix in 2010. The trio collaborated to create, write and star in the truTV comedy series Those Who Can't, which aired for three seasons. Since then, the three comics have continued hosting the popular podcast The Grawlix Saves the World, and they perform live together at the Bug Theatre on the last Saturday of each month.

Cayton-Holland also founded the multi-day High Plains Comedy Festival in 2013 "to showcase how funny Denver is and put the national spotlight on the Denver comedy scene once a year," he says.
His reflections on his formative years reveal a comedian unafraid to tackle adversity head-on. Performing in rowdy settings taught him the invaluable skill of commanding a room. "The Squire and Lion's Lair are rowdy and dirty, so you kind of had to get the audience's attention by yelling at them or doing something shocking or subversive," he recalls. "A move I would always do is talk about people who were not paying attention, and enough people would start looking at that person that they'd start to pay attention. I don't even know if these are valuable lessons, but I certainly learned how to get into a space and command a room."

Now that Cayton-Holland is sought out by audiences, he doesn't "have to attack people to get them to pay attention," he says. "But if I ever go into a setting and it’s less than ideal, other comics will say, ‘It doesn't look good out there,’ and I'm always just like, ‘Oh, that's fine. I've seen way, way worse.’ Those early club performances were wild and glorious and showed me the worst of comedy, so training there meant you got better."

Beyond the laughter, Cayton-Holland's journey has been shaped by profound personal challenges, most notably his younger sister's suicide in 2012. This tragedy, coming at a high point in his career, tested his resolve and led to a period of deep introspection. "I’ve had so many challenging moments, but the hardest one was losing my little sister," he says. "I went to Montreal for [Just for Laughs] New Faces of Comedy, which is the comedian's equivalent of the Super Bowl, and then she died like three days later. I was at the highest point I’ve ever been in life, and it was immediately followed by the lowest I’ve ever been, so that was certainly a challenge. I didn't want to do standup anymore. I was too fucked up.

"Finding the beauty in life again has been the biggest challenge I've ever had to face," he adds. "That's a pretty heavy answer, but that's the truth."
Comedy became not just a profession, but a lifeline, a way to navigate grief. Such themes are explored in his book, Tragedy Plus Time, and one-man show, Happy Place, which both provide insights into the therapeutic value of humor.

"I've been forced to realize how quickly life can be snuffed out and how precious our time on the planet is," Cayton-Holland says. "We’ll all be dead before you know it, so do you want to cry or do you want to laugh? I’ve done both a lot; I chose to laugh."

As he looks to the future, he remains committed to exploring new creative avenues, from a promising movie script "that has got a lot of traction" to the ongoing success of Happy Place, which he'll be performing around the country and hopes to bring off-Broadway in November.

When asked why he wanted to perform his twentieth-anniversary show at Comedy Works, Cayton-Holland says it's because the venue "was, and still is, every local comedian's goal." 

"I just think we're very lucky in Denver, given the size of the city, that we have Comedy Works," he notes. "Every comic you interview will tell you it’s one of the top five clubs in the country, and [owner] Wende Curtis has always been very cool to me. Once you do start headlining there, you're one of her guys. One of the reasons that Denver punches above its weight is because of the great indie scene and all the good comics that come out of that club. You're not going to get on that stage if you're garbage, and that ensures quality control.

"So when it was time to do a twentieth anniversary," he concludes, "it was obvious where: Denver, because it's my hometown, and Comedy Works, because it's my home stage."

Adam Cayton-Holland, Thursday, April 25, Comedy Works Downtown, 1226 15th Street. Get tickets at comedyworks.com.