After 21 Years in Comedy, Adam Cayton-Holland's Standup Is Still Standing

"I'm giving up," says Adam Cayton-Holland. "There's just nothing left to joke about, man."

Of course, he's joking when he says that. After two decades as a comedian, the 44-year-old lifelong Denverite still has plenty of fun to poke at just about everything. Case in point: his new comedy special, Twenty Years in Comedy and All I Got Was This Lousy Special, which is being released on Friday, March 28. It was recorded in April 2024 at the Lion's Lair at 2022 East Colfax Avenue, which just so happens to be the same open-mic comedy stage where Cayton-Holland first cracked wise before a live audience. This was back in 2004, when he had just started writing for Westword (his first piece was an essay in the Best of Denver issue). He was young. He was hungry. He thought he might even be funny.

Those three things provided enough fuel to launch an enduring career during which Cayton-Holland evolved from a nervous kid to a seasoned statesman of standup. That journey has taken him from lows (his Westword job was eliminated in the economic downturn of 2008) to crazy heights: his own three-season sitcom, Those Who Can't, on TruTV; the founding of Denver's annual High Plains Comedy Festival (the twelfth installment is set for September 18-20 this year); the pages of the Atlantic, Esquire and Variety; the sets of Conan, Comedy Central Presents and ABC's Happy Endings; the Simon & Schuster-published, Colorado Book Award-winning memoir Tragedy Plus Time, about the suicide of his sister; the writers' room of See You When I See You, an upcoming film adaptation of his book directed by Jay Duplass and starring, among others, Hope Davis and David Duchovny...

And then, well, all the way back to the Lion's Lair.

"Truly, I was not too analytic about it," he says of his decision to film Twenty Years at the legendarily seedy yet creative-incubating Lair, where generations of local comedians, musicians, DJs and barstool philosophers have had their talents nurtured. "I knew that my twentieth anniversary was coming up, because you remember these arbitrary milestones of your career. And that felt like a big one. I just thought, 'Well, what's something cool to do? Doing a show at the Lion's Lair, because you started there.'"

And what a start it was. Cayton-Holland admits he didn't do all that well at first — "When you're a young comedian at an open mic, I liken it to being a toddler," he says — but before long, the routines he'd been practicing in his bedroom mirror began to catch on. The modest digs of the Lair led to the big, high-profile room of the Comedy Works.

He also threw in his lot with fellow local comics Ben Roy and Andrew Overdahl; the trio dubbed themselves the Grawlix, and joined forces onstage and via podcasts before ultimately cowriting and costarring in Those Who Can't, which was set in a fictional Denver high school and ran from 2016 to 2019. The trio's long-running podcast, The Grawlix Saves the World, was just refreshed and relaunched this month as Advice Fight, a satirical take on call-in advice shows.



Through all this, the Lair beckoned. Directed and produced by Nick Holmby and Jacob Rupp of Denver's Dude, IDK Studios — Holmby and Cayton-Holland remain friends from the days when Holmby was a manager at Comedy Works and Cayton-Holland was still an unproven, wet-behind-the-ears prospect — Twenty Years is a blast (and not just from the past). Cayton-Holland is now a husband and the father of two, and he peppers his self-deprecating reminiscence of being a newbie comic with the current, middle-age-ish issues he can't help but find ridiculous: aging, crying, his lifelong and ever-shifting love of the Denver Broncos, fatherhood and the state of modern masculinity.

He doesn't shy away from a topic that the comedy world has been ablaze with lately: so-called wokeism.

"It pisses me off when comics use wokeism as a complaint. I think it just means those people are bad writers," he says. "I really hate a lot of shit in comedy right now, specifically the Joe Rogan-ification and Tony Hinchcliffe-ification of standup comedy. I see young comics starting to think that the ticket to success is being like these alt-right-adjacent fuckers who will have Alex Jones on their podcast, and it just breaks my heart.

"You can shit your pants right now," he adds. "Like, you can sneeze and just shit your pants. We're such fragile creatures. At any moment, anything can go wrong. It's a miracle you're upright and walking around. We're all weak. Being macho is so fucking absurd. Just let down your guard, dipshit."

On Twenty Years, though, everything goes right — there's not a shat pair of pants to be seen. Cayton-Holland is a duck in water at the Lair, and it shows in his warm banter and genial wit. It helps that over a hundred attendees packed the tiny venue for the show, which he is pretty certain was a violation of fire code. These are his people, his hometown fans. As his stories unspool and his punchlines pivot from poignant to surreal, the camera meanders and captures the Lair's shabby ambience. Aside from the copious laughter, it's a quiet triumph.
 "I didn't think I would do a special," he says. "I just thought, 'I'll tape it and clip it up, because that's the comedy landscape we live in.' It's just like, throw clips out on social media all the time. It's the short-attention-span theater of the Internet. You've got to be pumping shit out there. Then it turned out that people were really excited about the taping. We sold out one show and then two. Nick was like, 'This seems like a bigger deal. Let's really go at it.'"

He continues: "I hurriedly was like, 'Can I make a special out of the material I have right now?' I slapped it together. I didn't want it to be anything grandiose. I wanted it to be gritty. It's not like, 'Wow, what a profound statement on things.' It's not a tightly written hour. It's more like, 'Here's where I am and who I am at this moment.' I have lots of friends who are at the top of the game, making millions, and I would love to be there. But currently I'm able to sustain my life by waking up and creating things. I'm learning to take that as a win."

The final scene of Twenty Years shows Cayton-Holland sitting alone at the bar of the Lair. His set is done, and the place is empty. He addresses the viewer: "It would be cool if they said, when I'm dead and gone and it's all over, 'I saw Adam Cayton-Holland once.'" He pauses to stare pensively into the distance before adding: "'He was on all fours, retching in a field.'"

"I made that the last beat of the special because it's so fucking silly," he explains. "I run the High Plains Comedy Festival. I'm a super Denver booster, a DIY, scene-building type of guy, and I'm proud of that. At the end of the day, I am a Denver dude, and this is the iconic Denver dive bar that I started at. It's such a shithole, and it's a glorious shithole. That's just the absurdity of a career in the arts. It's absurd that I've been doing this for twenty years, and it went by like fucking that. It's all just silly and great and worth celebrating, but not taken too seriously."

Adam Cayton-Holland's comedy special, Twenty Years in Comedy and All I Got Was This Lousy Special, will be available to watch on YouTube at 6 p.m. Friday, March 28. Cayton-Holland also will sell vinyl of the album that night from 8-10 p.m. at Ratio Beerworks, 2920 Larimer Street.