How Improv Transforms Lives: Josie Whittlesey from Drama Club

Meet Josie Whittlesey, founder of @dramaclubnyc, a nonprofit bringing improv to incarcerated youth. In this interview she discusses the power of creativity to heal and transform and the inspiring impact that Drama Club has had.

Piper

Improv has the power to .......

What do you think?

Josie

I know it has the power to mitigate trauma, especially in adolescents with complex trauma.

Piper

That’s so interesting. Do you have anything to expand on that idea?

Josie

Yeah. There was a really fascinating study about the practice of 'yes, and' in improv. It creates a safe space for risk-taking and allows kids with complex trauma to explore within that safety. It’s been proven that it can even rewire neural pathways, which is incredible.

Piper

I completely agree. I’ve seen research on that too. When I run workshops, I notice shy kids or those hesitant to step outside their comfort zones transforming through improv. It really creates a safe, welcoming environment.

Piper

Your work with the Drama Club brings improv to incarcerated youth at Rikers Island, which is both innovative and challenging. What inspired you to start the Drama Club and bring improv to this community?

Josie

The short answer is that I became convinced theater training would be great for kids in confinement. Initially, I wanted to volunteer for someone already doing this work, but I couldn’t find anyone in New York. I found organizations working with adults, so I started volunteering at Sing Sing prison for two years.

Some of the men there encouraged me to start working with younger people. They told me, 'We wish we had something like this when we came through the system.' That really stuck with me. It took time to find juvenile detention centers, but once I did, it all came together. Rikers heard about us and invited us to work with their adolescents, and eventually, we expanded to young adults.

Piper

Improv is all about trust and vulnerability. How do you build trust with the youth, especially in such a constricting environment?

Josie

You have to be completely transparent. The kids pick up on insincerity instantly, so being 100% genuine is key. We do a lot of community-building games to warm up and establish trust. Now that we’ve been around for years, there’s usually at least one participant who’s worked with us before. This helps break the ice. Our teaching artists are also incredibly talented at gaining trust, and we often bring in social workers to provide additional support when someone is having a tough day.

Piper

At Drama Club, you also support youth in their transition back to their communities. How does the program help them after they leave, and what challenges do you face in maintaining those improv skills in a different environment?

Josie

It’s a work in progress. For kids under 18, there are anti-grooming laws that make it hard to stay in contact after they leave. We rely on relationships with their lawyers and social workers to bridge that gap.

For young adults at Rikers, they can reach out to us directly, but many don’t. They’re often returning to chaotic lives. Still, we’ve had success stories. One young man recently rejoined us and performed a powerful monologue about experiencing Christmas at home while thinking of his friends still at Rikers.

Piper

Is there a moment from a workshop or show that stands out to you as particularly funny or unexpected?

Josie

Oh, there are so many! One that comes to mind is from the early days when a couple was improvising a typical 'cheating boyfriend' scene. I encouraged them to make an unpredictable choice, and the boy got down on one knee and proposed! The kids lost their minds—it was hilarious but also made perfect sense in the scene. Another moment was darker but deeply impactful. A young man who had previously attempted suicide rejoined our group after months in mental observation. During an improv exercise, he played a character coming out to his father, which led to him coming out to the group in real life. It was such a brave and transformative moment, especially in such a hyper-masculine, homophobic environment.

Piper

Drama Club focuses on social and emotional learning. How do the skills built through improv translate to real-life success for the youth?

Josie

Our recidivism rate is significantly lower than the national average, which is around 40% for juveniles. Ours is in the teens. I believe the social and emotional learning from improv plays a big role in that—it helps them grow, develop better behaviors, and build confidence.

Piper

As someone who has been teaching improv for years, do you have any favorite games or exercises that you’d recommend, especially for younger kids?

Josie

I like games that involve the whole group, as elimination games can be tough for kids who get out early. One of my favorites is a game where the whole room writes phrases based on a prompt. Two players onstage receive these phrases during an improv scene and must incorporate them naturally.

Another great game involves everyone standing in a circle while one person in the middle tries to replace themselves with someone else. No one is ever 'out,' which keeps everyone engaged.