Windermere Prep alumna Ashley De La Rosa can’t wait to resume her role in the San Francisco Company’s production of ‘Hamilton.’
If you asked Gotha native Ashley De La Rosa in her high-school years where she saw herself in 10 years, she probably would not have mentioned Broadway.
In fact, it wasn’t until her senior year at Windermere Preparatory School — during which she competed on NBC’s “The Voice” — that she even saw any sign of a future in performing.
Now 26, De La Rosa has shown her 18-year-old self that hard work prevails. She made it to Broadway as a standby for Regina George and Gretchen Weiners in “Mean Girls” in 2018, and as Janelle Woods/Shirelle in “Beautiful: The Carole King Musical.”
Most recently, in November 2019, she assumed the role of Peggy/Maria in the San Francisco Company’s production of “Hamilton.” The COVID-19 pandemic has put that on hold for now, but in the meantime, De La Rosa also has found another passion in being an activist for social justice.
BORN TO PERFORM
Singing and acting was more of a hobby for De La Rosa until her senior year at Windermere Prep, when she auditioned for, competed in and made it to the Top 12 of “The Voice.”
“I auditioned for it sort of on a whim,” she said. “Then I actually got on ‘The Voice.’ I didn’t really expect much was going to come of it. Once we decided I was going to be on the show and what came next … it was my senior year, and that was where Windermere Prep kicked in with helping to facilitate the balance of being in California while completing the IB program.”
It was tough work, but De La Rosa said her teachers and tutor helped ensure she stayed on course academically while also pursuing a newfound dream.
“The school made a big banner for me and encouraged the students to vote, and just seeing the response from my classmates but also my teachers who really wanted to help me continue on (was great),” she said.
Upon graduation, De La Rosa attended Wellesley College for two years and studied international relations and chemistry. After those two years, she decided to shift gears to pursue her acting and singing career.
De La Rosa moved to New York City and studied at a conservatory for two years before completing the program and starting her professional career. She’s had some highlight moments on Broadway and on national tours, but there was always one in the back of her mind: “Hamilton.”
In fact, she auditioned for it three times before landing the role of Peggy/Maria with the San Francisco Company. De La Rosa started with that show in November 2019 and debuted in January 2020. Just a couple of months later, though, the arts came to a halt under COVID-19.
“Being in the show is everything and more that I imagined it would be,” she said. “The people are really great, and the message is extremely important. I’m really looking forward to getting back to doing that. It was something I worked so hard and so long for. It fills me with a lot of joy and pride to accomplish that.”
ACTIVISM AT WORK
Although she has her role to return to when it’s safe to do so, De La Rosa also has had more time in the past year to strengthen her connection with her passion for social justice. She said “Hamilton” is wonderful because it fosters a culture in which social justice is at the forefront of the conversation.
“Art and life reflect each other, and especially with the show ‘Hamilton,’ it’s like a mirror to society, because it’s something that did actually happen — but a lot of the roles are played by people of color,” she said. “We’re talking about people in the past, but the people on stage who are playing these characters are reflective of the make-up of our country right now. It’s a total melting pot of people on the stage, and I think that’s really inspiring. ‘Hamilton’ is one of the first — and one of the only — shows that does that, which is why I think they’re a great leader in the front of social justice, because they really do practice what they preach.”
“I also think the arts has a strong power to transform people’s lives and people’s mindsets and what they think. Having these conversations is important.” — Ashley De La Rosa
Although De La Rosa has always felt a pull toward advocacy work and activism, she said it wasn’t until the death of George Floyd and resurgence of the Black Lives Matter movement last summer — coupled with the pandemic and being out of work — that she was really able to dedicate time to it.
“I started working with an organization my friend created called Swing from Home,” she said. “All local candidates were going virtual, because they couldn’t knock on doors … and meet up and have rallies, so everything was on Zoom. I did phone banking for local progressive candidates all across the country from Montana to Maryland.”
De La Rosa said she is actively working with a couple of organizations at the moment. One is called Claim Our Space, which curates and supports events that aim to foster deeper community relationships and attain social justice. Another is Broadway for Racial Justice.
“With those organizations, I’ve really found that until the world can reflect a place that is equitable for everyone, then theater and even educational institutions, they’re not going to reflect that, either,” she said. “It’s less on the individual (level) and more systemic, and I think that’s what a lot of people have come to realize, too.
“I also think the arts has a strong power to transform people’s lives and people’s mindsets and what they think,” she said. “Having these conversations is important. I think it really kind of opens people up to change.”