Interview: Natasha Castillo Presents DARIN TO BE DIFFERENT at Don't Tell Mama
The Bobby Darin show runs 9/27, 10/11, and 10/24
Natasha Castillo, a Manhattan Association of Cabarets and Clubs (MAC) award nominee, is returning to the stage with a new cabaret that takes an intimate look at the lesser-known parts of Bobby Darin’s life. The show, which is a mixture of music and storytelling, will play Don’t Tell Mama on September 27th, October 11th, and October 24th.
Below, read a conversation with Natasha Castillo about Darin to Be Different
This conversation has been condensed and edited for clarity.
How did you get started in the world of theatre and cabaret?
Music had always been part of my life, but cabaret found me at exactly the moment I needed it most.
I've been singing for as long as I can remember—from performing for my family in the living room as a child to singing in choirs, a cappella groups, an alternative rock band in college, and later a wedding band. But after years away from performing, I found myself searching for a way back to music.
That's when I discovered the Singers Forum Open Mic, hosted by my late friend John Koprowski. What began as an open mic quickly became a community and ultimately led me to cabaret.
Through Singers Forum, I found Lennie Watts' Get Your Act Together class, which taught me how to shape songs into a cohesive story. The show I created there eventually evolved into my debut cabaret, Anything But Ordinary.
Looking back, cabaret gave me far more than a performance outlet. It gave me a creative home, lifelong friendships, and a way to connect with audiences through storytelling. Darin to Be Different is now my sixth cabaret show, and I still feel that same excitement every time I begin a new project.
How did the idea for Darin to Be Different come to be?
I've loved Bobby Darin's music for years, but what inspired this show wasn't just the music—it was the man behind it.
Most people know Bobby Darin as the charismatic performer who gave us hits like "Mack the Knife," "Splish Splash," and "Beyond the Sea." But as I learned more about his life, I discovered someone far more complex than the public image many of us know.
The idea for Darin to Be Different grew out of my desire to explore that side of him. I became fascinated by his ambition, his relationships, his sense of humor, his convictions, and the challenges he faced throughout his life. The more I learned, the more I felt there was a story worth telling—one that invites audiences to look beyond the legend and discover the person behind the spotlight.
The currently-running Broadway musical Just in Time is notably also taking a look at Bobby Darin’s life. Is your show taking a look at similar events, or are you looking at a different time of his life?
I thoroughly enjoyed Just in Time, starring Jonathan Groff. In fact, I saw it twice—once with my director and once with my music director. By the time it opened, I was already deep into developing Darin to Be Different, so it was fascinating to see another creative team's interpretation of Bobby Darin's story.
Because both shows are centered on Bobby Darin, there is naturally some overlap. However, our approaches are quite different. Just in Time celebrates the remarkable entertainer and public figure, while my show focuses on some of the lesser-known aspects of the man behind the fame.
What interested me most wasn't simply Bobby's success but his complexity—his friendships, relationships, convictions, personal struggles, and the experiences that shaped him. My goal is to help audiences see Bobby Darin not just as an icon but as a human being.
I think people who enjoy Just in Time may discover an entirely different perspective on Bobby Darin when they see Darin to Be Different.
What has been the most rewarding part of the project for you so far?
One of the things I love most about cabaret is the creative process itself.
You start with songs, stories, research, and ideas that may not seem connected at first. Then, through collaboration with a director and music director, those pieces gradually begin to take shape and reveal a story. Watching that transformation happen is one of the most rewarding parts of creating a show.
With Darin to Be Different, I had the added joy of working with my dream team, multi-award-winning director and cabaret wizard Lennie Watts and award-winning music director Ted Stafford, to uncover the many layers of Bobby Darin's life. I started this project because I loved his music, but as we explored his story together, I gained a much deeper appreciation for the person behind the songs.
There were so many moments during the process when we'd uncover a story or connection and think, "How does everyone not know this?" Those discoveries helped shape the show and made the journey incredibly exciting.
For me, the real magic is when all of those pieces—music, storytelling, research, and collaboration—finally come together and become something you can share with an audience.
What do you hope audiences will take away from Darin to Be Different?
I hope audiences leave with a deeper appreciation for Bobby Darin—not just as an entertainer, but as a person.
Many people know the famous songs and the larger-than-life performer. What surprised me during my research was how much resilience, complexity, and humanity existed behind that public image. He experienced tremendous success, personal heartbreak, unexpected discoveries about his own identity, and a constant awareness that life might be shorter than he hoped.
If audience members walk away feeling like they've met the person behind the legend, then I've accomplished what I set out to do. And if they leave wanting to revisit his music with fresh ears, that's even better.
Do you have anything else you would like to add?
One thing I've learned through cabaret is that none of us get here alone.
When I first found my way back to performing, I was welcomed into a community that encouraged me, challenged me, and gave me the confidence to grow as an artist. The Singers Forum Open Mic, hosted by my late friend John Koprowski, played a huge role in that journey.
John believed in creating a supportive space where performers could take risks, try new material, and simply enjoy sharing their love of music. His generosity and vision had a profound impact on me.
After John's passing, I wanted to help carry that spirit forward. That's how Spotlight on YOU Open Mic was born. Now in its ninth year, it has become a place where performers of all experience levels can come together, support one another, and share their artistry. It has also been incredibly rewarding to serve the cabaret community through my work with the Manhattan Association of Cabarets and Clubs (MAC), first as Treasurer and now as a member of the Board of Directors.
At its heart, whether I'm hosting an open mic or performing Darin to Be Different, it's all about the same thing: bringing people together through music, storytelling, and community.
And if someone reading this has always wanted to perform but doesn't know where to start, I encourage them to visit Spotlight on YOU Open Mic. You never know where that first step might lead.
Tickets for Natasha Castillo: Darin to Be Different at Don’t Tell Mama on September 27th and October 24th at 7 pm and October 11th at 4 pm are on sale here.
Learn more about Natasha Castillo here.
Learn more about Spotlight on YOU Open Mic here.
Photo Credit: Helane Blumfield
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