Vail Comedy Show Brings Leah Bonnema and Dustin Chafin to Gypsum

Aspen —“I want to drive straight through the middle,” Leah Bonnema said of Gypsum’s roundabouts. “The anxiety. I see them coming and panic.”

That is the primary concern for the Los Angeles comedy contingent descending on Eagle River Brewing Company this Thursday, August 26. The Vail Comedy Show returns to Gypsum, bringing former festival headliners Bonnema and Dustin Chafin to the valley. Mark Masters, a Denver comic, will host.

It’s not just a one-off gig. Masters confirmed this is the first of three shows in the coming months. The commitment suggests the organizers believe there’s enough local appetite to sustain a touring circuit that usually stays closer to the ski resorts.

Bonnema’s resume includes a stint on CBS’s “The Late Show with Stephen Colbert,” a book titled “The Holiday Breakdown,” and co-hosting the podcast “Were You Raised By Wolves?” She’s been around the block. She headlined the Vail Comedy Festival before. She knows the terrain, even if she’s still at war with the traffic circles.

Chafin brings HBO’s “Crashing” and SiriusXM credits to the table. He’s also got the Marc Maron stamp of approval. He appeared on the final season of Maron’s “WTF Podcast,” a career highlight he describes as “roasting, hanging with the cats, and seeing his vinyl collection.” It’s a big credit for a comedian who wants to talk shop with one of his all-time favorites.

Masters, the host, has had a varied season. He performed at a high school reunion for the class of 1986 in Casper, Wyoming, on one weekend. The next, he did a corporate private event in Denver, followed by a campground comedy show in the woods near Colorado Springs. If you can get a crowd to laugh in a campground, you can probably get them to laugh at the local taproom.

The immediate future holds more of the same. Vail Comedy Show returns to the same venue on Saturday, September 12. Winston Hodges, a top six finalist on the Netflix series “FUNNY AF with Kevin Hart,” will headline. Mary Spadaro from Boston will also perform.

Then comes the Mountain Fresh Comedy Festival on October 8. Andrew Orvedahl, who performed on “The Tonight Show with Jimmy Fallon,” will headline. The bill includes comics from Maine, Vermont, New York City, Texas, and Missouri. That’s a lot of geography for one small-town brewery.

Tickets are available at vailcomedyshow.com. The location is fixed: Eagle River Brewing Company. The dates are set. The talent is established.

The real question isn’t whether the jokes will land. It’s whether the locals will brave the roundabouts to hear Bonnema explain why she wants to drive straight through the center of them. For context, Gypsum has plenty of them. They are a defining feature of the local driving experience. If you can conquer the circle, you get the show. If not, you stay home and listen to the podcast.

Masters is already planning the next leg. The circuit is moving, and Gypsum is on the map. It’s a small venue, but the credentials of the headliners suggest this isn’t just a open-mic night with a higher price tag. It’s a curated event.

Bonnema is also busy. She’s starting back out on tour. She’s directing a short film she wrote, “MissConduct,” which won awards at script festivals. And, because perimenopause strikes when you least expect it, she’s working on a detective novel in the wee hours of the morning. She’s not just performing; she’s building a portfolio.

Chafin is still riding the high of that Maran interview. Masters is still figuring out where the next corporate gig is. The show goes on.

Locals should check the website for ticket availability. The brewery will be full. The roundabouts will be navigated. And somewhere, a comedian is wondering if they parked in the right spot near the woods.