When Adam Cayton-Holland started the High Plains Comedy Festival with Karen Wachtel in 2013, he had to beg his fellow standup friends to come.

Maybe it was the pitch.

“I was like, ‘How would you like me to underpay you to come and have a great weekend in Denver?’” he said. (And yet, they did.)

Fast forward to 2024, and High Plains is now not only the largest comedy festival in Denver, it is considered one of the most talent-packed yuk fests in the country, period.

No surprise that Cayton-Holland has since changed positions on the comedy diamond from pitcher to catcher. “In the last couple of years,” he said, “it’s shifted more to, ‘Can I please come do your festival?’”

The 2024 High Plains Comedy Festival will gather about 60 local and 40 national comics this weekend for 32 ticketed events, most in five nearby venues in the historic Baker neighborhood of South Broadway, culminating with a closing headlining show starring Bob The Drag Queen on Saturday night at the Paramount Theatre.

“Think of it as a music festival for comedy,” Cayton-Holland said. “Everything is walkable and within a close distance so you can just get in and out and see so many performers that you may not have heard of – but you should have.”

And what about Bob? Well, Bob The Drag Queen is perhaps the most recognizable winner from the hit show “RuPaul’s Drag Race,” having taken the tiara back in Season 8 in 2016. Bob is now a podcaster, TV host, actor and activist who opened for Madonna on her recent career-spanning “Celebration” tour. Cayton-Holland thinks Bob will be the perfect way to bring the weekend to a close.

“In my opinion, Bob is the funniest drag queen to come out of that show,” he said. “I think a lot of drag queens are hilarious to the specific space of drag, but I think Bob really crosses over to comedy.”

Still, as a former journalist for Westword, I had to ask Cayton-Holland if he’s rankled by the upper-case article in that name, “Bob The Drag Queen.” After all, the Associated Press Style Book, considered the industry standard, calls for a lower-case “the.” Cayton-Holland did not take the bait.

“I don’t question how people want to be identified,” he said. “I’ve decided whatever grammar you want around your name is fine. In fact, I’ve been playing around with lowercase a lot myself.”

Now, that’s what you call allyship.

“Play with the language,” he went on. “I say these rules are meant to be broken.”

Six intriguing comics to catch

The bulk of the festival will be short, grouped stand-up routines concentrated at venues such as the hi-dive and HQ near Broadway and Ellsworth Avenue. Here are six intriguing standups to watch:

1. Rory Scovel, a perennial High Plains fest fave who also happens to be blowing up right now as an actor, will be all over Denver this weekend. He just finished a monumental run as Rose Byrne’s husband in the three-season Apple TV series “Physical,” and soon will be seen starring alongside Reese Witherspoon and Will Ferrell in the Amazon romantic comedy “You’re Cordially Invited.” His four festival appearances will culminate in a rare, one-hour, one-comedian set of what is being billed as entirely improvised standup at 7 p.m. Saturday at HQ. He’ll also be sticking around the area to play the Comedy Fort from Oct. 1-2 in Fort Collins.

2. Chris Estrada is another accomplished screen actor who created and stars in the Hulu series “This Fool.” One of his four short sets will include a dedicated program of five comics performing in Spanish at 7 p.m. Saturday at Chaos Bloom. Like me, Estrada has a cat that he takes out for walks.

3. Denver audiences might remember Broadway actor A.J. Holmes from his run as Elder Cunningham in the 2013 national touring production of “The Book of Mormon.” He’s engaged to comic Caitlin Cook, who has two solo standup gigs this weekend and a third with Holmes called “2/3rds of a Threesome.” That’s a widely praised cabaret show they’ve developed that is made up of their own original songs often accompanied by their better third – special guests from the worlds of Broadway and standup. “Caitlin has a one-woman bathroom graffiti musical called ‘The Writing on the Stall’ that has been killing it off-Broadway for years,” Cayton-Holland said. “And they do musical comedy quite well together.” 10 p.m. Saturday at the Skylark Lounge.

4. Repping the 303 is accomplished standup and local stage actor Jenae Burris, whose credits include the Colorado Shakespeare Festival, the Denver Center for the Performing Arts and a True West Award-winning turn in “Queen’s Girl In The World” at the Aurora Fox. This past summer, Burris became the first woman to host the Film on the Rocks season at Red Rocks. Oh, and did we mention? She’s funny! Especially talking about her new real-life human child. 6 p.m.Saturday at the hi-dive cq.

5. Katherine Blanford has described herself as “a Kentucky-born comedian with a Golden Retriever presence” that has made her a standup fan favorite. She’s known for confessing her Southern family’s secrets and tales from her awkward adolescent years. She’s co-host of a juicy podcast called “Cheaties” that follows two comedians sharing stories of heartbreak. “Not bad for a girl whose parents are cousins,” she says of herself.

6. The entire High Plains festival is curated, which to a degree means Cayton-Holland has hand-picked all 100 comedians. And one he’s super-pleased to introduce to Denver audiences is the mysteriously one-named Atlanta comic Mandal, who recently opened for John Mulaney. “He’s definitely one that I would tell people to come see wherever he’s performing,” Cayton-Holland said. Of his own name, Mandal said, “It can mean many things. Today it’s ‘man sandal.’” Among his three fest appearances is 8 p.m. Friday at HQ.

Podcasts and much more

Beyond standup sets, the fest has a wide range of comedy genres, programs and formats planned. For example, Wednesday’s designated festival launch event was the regularly scheduled monthly gathering of “The Narrators” at Buntport Theater. That’s Andrew Orvedahl’s award-winning storytelling series where comics tell true, real-life stories based on a designated theme – this month, it was “Selling Out.”

Five podcast episodes will be recorded live from the festival, including “The Grawlix Saves the World,” a popular comedy-advice pod featuring real-life buddies Cayton-Holland, Orvedahl and Ben Roy. Each episode culminates with the comedy supertrio fighting to the death over who gave the best advice to that week’s reader-submitted problem. And having a studio audience at 4 p.m. Saturday at the Skylark Lounge means festival attendees will get to weigh in on the advice the hosts have given. “That is going to be insane,” said Cayton-Holland, who has invited comics Laura Peek and Josh Gondelma to join in on the insanity.

Other live podcasts will include “All Fantasy Everything Live” – a show where funny people gather to conduct fantasy sports league-like drafts for everything from pop culture to music stars to sandwiches (6 p.m. Friday at HQ and 6 p.m. Saturday at the Skylark Lounge) Also: Chubby Behemoth Live (Denver comedians Sam Tallent and Nathan Lund, 5 p.m. Saturday at HQ); and “Some of This is Bad Live,” described as “a chaotic tornado of (bleep)-talking by Colton Dowling and Dylan Carlino (5 p.m., Saturday, Chaos Bloom).

And while High Plains does not accept submissions from wannabe standups, significantly reducing the cringe potential when festivals are open to all-comers, there is one opportunity for dreamers to stand up and do standup – and that is an open-mic set at the not-yet-relocated Mutiny Information Cafe lasting from 7-10 p.m. Friday.

“The thing I’m happiest about is that the festival is still very much a mom-and-pop operation,” said Cayton-Holland. “It’s still all about the love of the game, and I’m just thrilled that, 11 years in, I’m still able to attract the caliber of comedian that comes every year.”