Jennifer Caress on Whimsicult, Improv, and The Pool at Peak Improv Theater Colorado Springs
Jennifer Caress is a writer, actor, and improviser who found her creative home at Peak Improv Theater. A founding member of Whimsicult, Jennifer brings both wit and warmth to the stage, whether she’s exploring improv, sketch, or her original dramatic play The Pool. Audiences can catch The Pool during its Colorado Springs run at the Millibo Art Theatre on September 19–21 and 26–28. With a background in novels, scripts, and performance, Jennifer embodies the spirit of saying “yes, and” to every creative challenge.
PiT: The positive feedback you received after taking an actor’s class inspired you to join an improv class. What was that feedback and how did it translate to improv?
Jennifer Caress: Oh, good question. In the acting class, I was good with connecting to the audience, even through the camera. The acting teacher was sick one night or wasn’t able to attend the acting class. One of the students was Meggan Hyde, a co-owner of Peak Improv Theater and also a brilliant improv teacher. She said I could teach improv that night night. I’d never done it before. I knew what it was. Of course, I was absolutely petrified, and I very timidly would do each exercise she gave us. But then someone just said, ‘Hey, you’re funny, you’re good at this.’ And that was all I needed to keep going. When Peak Improv Theater opened, I was student Number One. I continued to take class after class after class and eventually joined my own improv team.
PiT: We still think you’re Number One. What are all the classes you’ve taken?
Jennifer Caress: Oh, heck, obviously Improv 101, Intermediate, Advanced. I’ve taken Stand Up and Comedy Sketch Writing. I’m doing Musical Improv now.
PiT: 2 Tell me about Whimsicult.
Jennifer Caress: We were all students of Peak Improv classes, and then they held auditions one day to be an in-house troupe of the Peak Improv Theater. A lot of us met at those auditions, and there’s about six of us now. We kind of rotate in and out as life happens. We’ve been going since about, I think, February of 2025. We’re growing every day. It’s so so fun to be a part of like minded people. We’re all a little bit weird, but always intent on being creative.
PiT: What classes did to take before you felt inspired to join a troupe?
Jennifer Caress: The basics: Improv 101, Intermediate, Advanced. You have to know how to roll with the punches. And improv is definitely a muscle. The more you use it, the stronger it gets. Improv is really therapeutic if because you are forced to be in the moment—outside of whatever else is going on your life. It’s brilliant. It’s wonderful. And it’s a really good way to connect with your community as a loner, as an introvert. That’s really hard to do, but it’s easier when you have an incredible, warm community like the PiT.
PiT: What kind of commitments are there to be in a troupe?
Jennifer Caress: We practice once a week. I’m not gonna say you have to, but we do ask that you show up to every practice, or as many practices as you can. Myself, I’m not able to make every practice, because life happens. But show up to as many as you can. There’s a show once a month, so be at that show once a month, if you can be there for your teammates, for yourself.
PiT: What are the unexpected benefits of performing in a troupe?
Jennifer Caress: Friends. Improv is a great way to bond with people and that I wouldn’t normally introduce myself to or make friends with. They’re all very, very nice, of course, but we just run in different circles and have different interests, but improv is definitely the one way that we connect. I think that’s probably the greatest benefit, besides being in front of an audience and making people laugh and telling a story. Improv doesn’t always have to be comedy. Sometimes it’s just be about a story that connects with people in the audience.
Huge thanks to Jennifer Caress for sharing her journey from novels to improv, from page to stage. Want to hear more about her work with Whimsicult and her play The Pool? Watch the full interview now on our YouTube channel.
