Pursuing a career in standup comedy is a lonesome journey through the gloom of uncertainty, with nothing but self-doubt as your constant companion. Competition is fierce and benchmarks of progress are few and far between. For a comedian fumbling through this desert of opportunity, a home club is both a welcome oasis and a base camp where you can return for shelter from the wilds of your ambitions. But when that home club happens to be a famously exclusive club of international renown like Denver's Comedy Works, base camp can feel awfully close to the summit. As Brent Gill, one of Denver's hardest-working comics, prepares to take the vaunted Comedy Works stage for his first headlining engagement, we reached out to Gill and a rogue's gallery of Comedy Works regulars to ask about reaching this coveted milestone in their own lonesome quests.
"For me, the first time I headlined was one of the most validating and intimidating experiences I had up to that point in my comedy career," remembers Troy Walker, a comic whose formative successes at the club's New Faces contest have been followed by highlights such as talent agency representation and an appearance on The Late Late Show. "You get to show everyone —all the people who came to open mics and supported your shows over the years— what you've built," Walker continues. "It's also your chance to show everyone you know outside of comedy what you've been up to all these years when you weren't hanging with them on weekends."
"There is something special to being in the rotation there," Gill effuses. "When you say 'I’m a regular at the Comedy Works in Denver,' it carries weight. It’s not like saying, 'I’m a regular at Uncle Fucker’s Chuckle Hut in Podunk, Kansas.' It showed me I was making progress in the right direction." Gill joined the regular roster at the club —a ruthlessly curated roster of a select few locals— in 2011, and has spent the subsequent years diligently signing up for emcee and feature spots on the weekends, warming up audiences for national headliners with the requisite TV credits to draw crowds.
"Headlining at Comedy Works is an elusive credit," explains club regular Deacon Gray. "The standard at the club is so high that most comics never make it to the point where it’s their name on the ticket." Furthermore, local headliners almost never have access to the prime weekend show real estate, and instead are faced with the challenge of filling seats on weeknights and holidays.
Frequent headliner and former Westword scribe Adam Cayton-Holland offers an apt metaphor: "It's like your dad finally trusts you to drive his fancy car. He's that confidant in you. He's that impressed with your ability now. Except in this example 'your dad' is actually 'your mom' in the form of Wende Curtis." Cayton-Holland's ascendant television career is itself a testament to that early vote of confidence — but despite the display of good faith from the club, Cayton-Holland remained hard at work on all things Grawlix and co-created the High Plains Comedy Festival to highlight the scene that had supported his rise. "I remember printing up fliers for my first show to pack it out," he says. "I was so excited. I still have that flier in a drawer somewhere. You never forget your first."
Gill keeps true to his Denver scene roots with a hand-drawn flyer.
The path to this definitive achievement is obscure and unique to each traveler. For Gill, it has wound far and wide, including years of unglamorous road gigs and self-started efforts. While not every endeavor has proved as successfully adaptable as his Infauxmation! news parody or consistently packed houses like the weekly Boulder Comedy Show at the Bohemian Biergarten, the one constant in Gill's career has been his own relentless hustle. From his early days on a now-defunct marijuana radio station, Gill — who wisely abandoned his original stage name "Brent The Great" — has stood apart for his fearlessness and bluster.
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"One of the hard things about comedy is there is not a 'right way' to do it, but apparently I am doing something right," Gill concedes. "At the same time, headlining Comedy Works for two days is not the end goal. I still have a lot of work left to do." After all, while reaching a milestone might be gratifying, another distinguishing characteristic of a comedian's lonesome journey is that it never ends.
Gill takes the stage at 7:30 p.m. Tuesday, November 17, at Comedy Works South. At 8 p.m. on Wednesday, November 17, he'll be slinging jokes at Comedy Works Downtown. Tickets for either show are $12 on the Comedy Works' website.
Follow Byron Graham on twitter @ByronFG for more mildly amusing sequences of words.