Hailey Kilgore Sings Out

TONY AWARD NOMINEE Hailey Kilgore doesn’t remember a time she didn’t love theatre. The Thespian alum credits her parents ― her mom is an actor and teacher; her dad ran a Portland, Oregon, theatre company for several years ― with launching her passion for the arts.

“When I was a kid, we did everything,” Kilgore said. “We went to museums. We would go to the park and listen to live music. It was all art, and it was all almost like a form of communication. We would have these amazing family conversations and discussions afterward that would stem from the thing we would experience.”

Hailey Kilgore

Now, Kilgore wants to ensure every young person has similar opportunities. Seeing the challenges facing school theatre programs, many of which lost significant portions of their annual revenue when forced to cancel spring 2020 productions in light of the COVID-19 pandemic, Kilgore knew she had to take action. So, the 21-year-old adopted a new title as executive producer of Project Sing Out!, a one-night only event to raise money for the Educational Theatre Foundation’s Thespian Relief Fund supporting arts education, especially in low-income communities and communities of color.

Project Sing Out! will be livestreamed on Playbill’s YouTube and Facebook channels on Monday, July 20, at 7 p.m. Eastern time. The special will feature a combination of musical and spoken word performances, plus appearances by a virtual who’s-who of the Broadway and entertainment worlds, including Chita Rivera, Don Cheadle, Vanessa Williams, Audra McDonald, Brandon Victor Dixon, Javier Muñoz, Ali Stroker, Ramin Karimloo, and Jordan Fisher, to name a few.

Kilgore says she was moved by the idea of so many students missing out on school milestones. “My mom’s a teacher, so I remember her bringing her first box of stuff home, the emotional turmoil,” she said. “All of these students who had a creative outlet, a creative safe space, they don’t have that anymore. … All these students who had musicals, who had showcases, who were graduating, who were meeting agents, who were getting ready for the International Thespian Festival ― all that’s gone. I couldn’t imagine not being able to do that because, quite frankly, for some students theatre is the lifeline for them in high school.”

By the time she was inducted in Thespian Troupe 2351 at Clackamas High School her freshman year, Kilgore had already amassed an impressive theatre resume. She soon added professional credits in productions of Ain’t Misbehavin’ and Our Town at Portland Center Stage.

Though she was familiar with the business side of theatre, Kilgore says she delighted in the community she found in the Clackamas program. “I loved my drama teacher, Ms. [Carrie] Vincent, who just retired this year,” Kilgore said. “We were a program that was not well funded, and we found ways to make money. We had so many great people who would come in from the professional world in downtown Portland and donate their time. She always found a way to make everything special for us. I remember when we were inducted into the Thespian Society. It’s this really big thing, and she makes it really special. And it wasn’t about how now you’re going to be able to go to regionals and maybe go to state. It was, ‘You are in a family. You are part of a community and a group of people that is so special and will work so hard.’”

As she continued to book a growing number of professional roles, Kilgore transferred to Clackamas Web Academy her junior year to finish her high school degree online, simultaneously taking community college courses. She graduated a year early and headed to American Musical and Dramatic Academy’s (AMDA) BFA program in New York City. While still a student, she was encouraged to attend an audition for the Broadway revival of Once on This Island, a full-circle moment for Kilgore, who’d been forced to drop out of her high school’s production for a professional job.

She almost didn’t go, initially opting out of the open call in New York City that concluded the international search for the show’s leading role of Ti Moune. “My mom emailed me the audition form, and she’s like, ‘You should do it,’” Kilgore said. “And I said, ‘No, I need to get my degree.’” But then Kilgore received a call from the casting company asking if she’d audition for director Michael Arden, choreographer Camille A. Brown, and writers Lynn Ahrens and Stephen Flaherty. “It’s something that reminds me that the right project, if it’s for you, will be for you,” she said.

Kilgore participated in months of workshops before earning an invitation to join the Broadway cast. She was just 19 when the role won her a 2018 Tony nomination. “The fact that I was being given the opportunity to be a young, Black girl onstage that other young, Black girls could see was really special to me,” Kilgore said, “and scary because there were a lot of expectations.”

Though her journey to Broadway may be atypical, Kilgore wants to ensure it’s not an anomaly. When the pandemic hit, she said, “The Broadway community was already working to raise money for each other. And I [felt] we also had to think about the next generation. They’ve lost a lot. There was also that fear of knowing that cities and states are going to have to make budget cuts. Theatres were already starting to go.”

So, Kilgore reached out to friends, including Once on This Island producer Yael Silver. What started as a small idea soon blossomed into something beyond even Kilgore’s imagination. “We put together a team, and we made a few phone calls and sent out a few texts and emails,” Kilgore explained. “And we said, ‘OK, let’s reach for the stars. Let’s call Audra ― she’s not going to answer, but let’s call her.’ And people just started saying yes, and so selflessly.

“It’s a huge honor for me because technically I’m still a newbie in the business, and I’ve been doing this since I was 9,” Kilgore continued. “People just started saying yes, and the most amazing thing about it all is the fact that these people were seeing beyond themselves. … It’s also living proof that young people can be leaders. We’ve seen this many times. Young people can take the lead.”

She encourages other Thespians to keep proving that mantra in whatever path they choose. “Be excited,” she said. “Instead of fearing the unknown, you have to be excited for the unknown. And do the work, then everything else happens the way it’s supposed to. You can only be where you are in that given moment. You can’t be anywhere else.”

Though initially intimidated by the scale of Project Sing Out!, Kilgore says the undertaking has taught her a great deal. “The best part has been jumping in with both feet,” she said. “And we jumped into the deep end, for sure. My hands are full but in the best way because it’s teaching me continued leadership skills. Also, as a young Black woman in this industry: Wow, we are capable of doing so much, even young people. Anyone ― any age, any ethnicity, from any background ― can take the lead if you bring the right people together. If you bring in people who believe in you and the vision, as I’m learning, you can do amazing things.”

Still, Kilgore is quick to deflect attention from her accomplishment, insisting the focus remain on the cause. “It’s about making sure people who are coming into this [industry] after me are taken care of,” she said. “That’s the bottom line. When I look at high school students, especially the ones who know this is what they want to do, I immediately don’t see them as students anymore. They’re co-workers. I’m looking at them from another side of the table right now, but in four or five years. … I don’t see them as kids that do theatre. I see them as young professionals training to take on the world.

“Because these are not just future actors and directors and producers and set designers we’re talking about,” Kilgore stressed. “We’re talking about doctors and lawyers and teachers and mayors. And maybe the president of the United States will be a Thespian. I’m sure, eventually, we’ll have one. We have to continue to nourish that. It’s not a choice.”

Learn more on the Project Sing Out! website.