If you know anything about theater, you know the Jimmy Awards are a big deal. They’re the country’s highest honor for high school musical theater, and former winners and nominees include the likes of Eva Noblezada, Andrew Barth Feldman, and Reneé Rapp. Now that list includes Milton High School rising senior Jake James.
On June 22, Jake James won the Jimmy Award for Best Leading Actor. To qualify for the Jimmys, he won the Shuler Hensley Award – Georgia’s national high school musical theater award – for his performance as Jacob in “Water for Elephants.”
The 17 year old won for his performance of “It’s Hard to Speak My Heart,” a song from the musical “Parade,” which tells the Atlanta story of Leo Frank, a Jewish man who was convicted for the murder of 13-year-old Mary Phagan in 1913.
After his win, I spoke with James about his journey to the Jimmys. This interview has been edited for length and clarity.

I’d love to hear just a little bit about how you first came to musical theater. How long have you been involved in this, and how did you realize you loved it so much?
Jake James: I always played baseball growing up. I was into baseball, and then theater kind of came along right at the end of elementary school/beginning of middle school when my sister kind of roped me into a children’s theater production of “The Lion King Jr.” That was the first one I ever did. It was a summer camp, month-long thing, and I met all these kids that were in theater. It was such a good atmosphere, and I enjoyed going there so much. I was like, this is like a group of people that I want to be with.
I kept doing junior shows there at the children’s theater, and then fell in love with it and started taking it more seriously in high school. But also, baseball was always my number one priority. I always thought of theater as more of a hobby, as something I’d do on the side. Then I was like, shoot – maybe I could actually take this pretty far. I feel like I’m getting the hang of this. It wasn’t until last year that I actually ended up quitting baseball and pursuing this as full time.
Those were two very time-consuming hobbies you picked.
James: One hundred percent. I was playing all year long, so theater was always second priority for me. But now it’s number one.
So this is what you want to do professionally after you graduate?
James: Yeah, that’s the goal. I wanna go to college and be on Broadway. Maybe go to Hollywood, do movies – that’d be really cool.
Leading up to the Jimmy Awards, I know that you won the Shuler Hensley Award for your role as Jacob in “Water for Elephants.” Talk to me about that win and that whole experience.
James: That was really cool. I had been nominated the year before for Gomez in “The Addams Family.” That week, where we’re just rehearsing the show – and the winners are already chosen, but we don’t know them yet until the day of – I keep saying, every time I go to the Shulers, and I’m in that rehearsal process, everyone is so nice. You don’t go anywhere these days where everyone is actively a nice person, and I just remember going there and feeling so welcome and at home with everyone. We spent a lot of time together that week, and those are the best people to be around. It was really cool to see, and have my friend Hayden [Poe] win that year, and then the next year I was able to win and go to the Jimmys and share the same experience that he had.
Talk about the process of going from winning at the Shulers heading into the Jimmy Awards.
James: Every state has regional award programs. Some have multiple, some have one. Georgia only has one, and so the winners of those regional programs then go to the Jimmys. That means once you win, you’re eligible to go to the Jimmys. Then, you have to send in interview questions and certain applications so that you’re able to be qualified as a nominee. But as long as you win your regional program, you’re eligible to go to the Jimmys.
How did you choose the song “It’s Hard to Speak My Heart?”
James: Before we left, we had to have four songs that could possibly be that song. We had to go with four choices. When we got into the finalist coaching, which is when you work with your finalist coach and pick one of those four, I only really wanted to do two of them … I sang “I Am Adolpho” and “It’s Hard to Speak My Heart.”
We actually ended up choosing “I Am Adolpho.” Then I went back to my dorm that night, and I was like, “It doesn’t feel right. Something doesn’t feel right.” My gut was telling me that wasn’t the right choice. I woke up the next morning, and then we went back into the coaching. I told her, I don’t think this is the song. This is not what I want to use to present myself and represent myself in front of all those important people in the industry. She ended up pulling a string for me and switching the song, because she had already submitted the application. I’m so grateful for that, because I can’t even imagine what would have happened.
Once I chose “It’s Hard to Speak my Heart,” I had done plenty of research on that song. It ties back to Georgia and my hometown. It’s a real thing that happened in history. I did a lot of research on the Leo Frank case. I talked to directors who have directed the show. My accompanist at my conservatory, she actually goes to the same synagogue, the same Jewish temple that Leo Frank went to … There were a lot of ties back to home, and a lot of really cool things I learned while doing research for the song. As much as no one’s gonna watch someone sing a song and see all the research they did, I feel like it reflects in the way that you perform the song. No one’s gonna know exactly why, but they can tell that something is going on in your head. You can tell when somebody did the work, and that’s been the most rewarding feedback, is that people are like, “I could tell that you really knew what you were talking about.”
What are some of the things that you learned at the Jimmys that you think helped you performance-wise?
James: There was a lot of throwing spaghetti at a wall and seeing what works, which is a really vulnerable thing to do, especially when you’re in a room with seven other amazing people that are watching you – and, I mean, secretly judging you in their mind. [Laughs] You know that they’re doing that! So when you’re with these coaches, and they’re telling you to try other things to get you out of your habits – because everybody’s been rehearsing their songs like, 50 times – so getting out of your comfort zone, trying new things just to keep it fresh, I think that really helped when I was practicing on my own. Figuring out new things I could work and couldn’t work.
Also, watching other people’s performances and other people get notes and other people get coached also really helps, because there’s so much stuff that they get that you can also apply to yourself. I was taking notes all the time during the coachings. I’d never done that before.
Had you been to New York before?
James: I have with my family. But that was my first time performing on a Broadway stage, and that was really cool.
How did that feel, and how did it feel when you won?
James: I never imagined that if I were to be on Broadway for the first time, that [this] would be how – at a high school awards show, or when I’m 17. So that was really crazy, because that’s way before I thought that would ever happen, if it happened. It was really cool to share that experience with everyone. It had been, like, 10 days, and we’d been making friends. They were really close friends, and we were all able to have that at the same time, which was really cool.
