Every performing artist has a eureka moment when, for the first time, they make that vital connection between themselves and their audience, setting off an endorphin rush they’ll likely be chasing after for the rest of their lives.

In Charles Grant’s case, that flash came at a young age when, after transferring to a public school in his former hometown of Bellflower, California, he auditioned for a role in Choices Count! The play, he remembers, “was all about kindness and communication and how to get along with each other.”

“I remember being on stage saying lines and people laughing and responding to me,” Grant continues. “And it was in that moment that I was like, ‘Oh, live performances. There’s something here.’”

Since then, the 30-year-old has dedicated himself to trying to capture that same feeling for both himself and the many people who are part of Portland’s rich theater community. For the past eight years, Grant has served as producing director for Portland Playhouse, a nonprofit theater whose founders have been dedicated to presenting works from a diverse array of creatives while honoring the heritage of the historically Black neighborhood where they stage their productions.

What began as a simple apprenticeship for Grant has become a full-time job with Portland Playhouse, with Grant and the dedicated staff helping to produce around four plays each year. During his tenure with the theater, productions have included their ongoing stagings of August Wilson’s Pittsburgh Cycle, family-friendly fare like A Christmas Carol and Matilda The Musical, and challenging new work like Grant’s own Matter, a solo show inspired by the ongoing cycle of police brutality and gun violence meted out upon Black men.

All that would be reason enough to honor Grant with this year’s Skidmore Prize, but as anyone who has worked with him will tell you, what truly makes him stand out is the effort he puts into keeping Portland Playhouse as inclusive as possible and building relationships with local schools and small businesses. He and the team have brought their educational programs everywhere, from Harriet Tubman Middle School to Coffee Creek Correctional Facility, and offered apprenticeships for budding actors and directors and Portland Playhouse’s Emergent Activist Project, which teaches young people about bringing social justice practices into their communities.

“When I first moved to Portland, I was like, ‘I’m going to do this 10-month apprenticeship and then I’m going to go to New York City. I’m going to do Broadway,’” says Grant. “But soon into the apprenticeship, I was like, ‘Oh, I feel like I’m really building a community here.’ And that’s what theater has always been about for me. It’s about collaboration. It’s about the opportunity to get to work with other people. That’s always been the goal.”

As Grant looks ahead to what comes next as he helps lead Portland Playhouse into an uncertain future, he keeps coming back to what he feels are two key pillars of the performing arts: collaborating and gathering.

“There’s dance. There’s going to a museum. There’s going to a concert. There’s all these different ways we gather,” he says. “But what is it about live theater that is so different from all those things and it’s about gathering and collaboration? The audience is the final character. Once they join, we really get to go on this journey together. But what happens after the play? What are the conversations people are having after they’ve seen a play? How are they different? How are they thinking differently? When I think about where we go from here: new work and continuing to have conversations that actually impact the city of Portland and beyond.”