Dawn Derow is an award-winning vocalist, songwriter, recording artist and performer known for her musical versatility. Born and raised in Cape Cod, Massachusetts, she holds a Bachelor of Music degree in Vocal Performance 
from the Boston Conservatory at Berklee, trained in classical vocal techniques. Transitioning to cabaret, Derow has performed on major New York stages and has a discography that includes My Ship: Songs from 1930-1944 and Symphony of Birch.
She’ll present Sing Happy on Tuesday, November 18 and Monday, December 1, both at 7 PM at The Triad Theater. The show is a revue celebrating the unforgettable women of Kander and Ebb, with direction by the award-winning David Sabella (Chicago), choreography by Jason Reiff, and at the piano, music director-arranger Ian Herman (Grease).
(Photo credit: Joe Manta)
NiteLife Exchange (NLE) asks Dawn Derow (DD) Six Questions:
NLE: You’re celebrating your milestone 50th birthday with a self-produced revue, Sing Happy, spotlighting the fierce women of Kander & Ebb musicals. What inspired you to honor this particular songwriting team — and these particular women — at this moment in your life and career?
DD: Because no one writes for women like Kander and Ebb. Their characters are complicated, sensual, messy, brave — they own their flaws and their fire. I like that!! At this point in my life, I relate to that. I’ve lived enough, loved 
enough, and fallen on my face enough to understand the kind of truth those women sing about. So Sing Happy felt like the perfect way to celebrate 50 — which is why I booked my NYC debut of this show to bookend my actual Birthday. (Nov 18 is the first show and Dec 1 is the second.. My 50th is Nov 24th) It’s my love letter to some of my favorite bold bad ass women birthed by this Broadway team!
NLE: Sing Happy coincides with both your birthday and the 50th anniversary of Chicago. Do you see parallels between your own evolution as a performer and the timeless, unapologetic characters Kander & Ebb created?
DD: Oh, absolutely. Those women — Velma, Roxie, Mama Morton — they don’t wait to be chosen; they choose themselves. After all, they sing it loud and clear: “I am my own best friend.” That’s a lesson I’ve learned, too. For 17 years, while producing shows in this cabaret community, I’ve continued to create my own opportunities and carve out my path. Sometimes
that means shedding a little excess baggage and moving forward with clarity and purpose.
And speaking of Chicago, my brilliant director David Sabella actually originated the role of Mary Sunshine on Broadway 30 years ago — that wonderfully surprising character who sings in high tenor falsetto! He recently stepped back into the role this past August, and I had the joy of seeing him perform. There’s something incredibly full-circle about that — watching David return to his roots while he helps me step boldly into this new chapter of mine.
The women of Chicago are survivors and so am I. They remind us that reinvention is a lifelong act, and the spotlight shines brightest when you stop apologizing for who you are.
NLE: You’ve won three MAC Awards and a Bistro Award for your work in cabaret — not to mention your recent triumph as Francesca in The Bridges of Madison County. How do you balance the emotional depth of musical theatre with the intimacy and storytelling of cabaret?
DD: Great fucking question – thanks for asking it!!! It’s all storytelling and a willingness to be vulnerable. Whether I’m on a big stage in a dark theatre or five feet from someone’s martini glass. Cabaret is theatre stripped of scenery and pretense. You can’t hide from the intimacy, you have to be real because you, the Singer, have chosen to share a message… whatever that might be in THIS moment.
The Bridges of Madison County, playing “Francesca” gave me a deep emotional well to draw from and cabaret lets me pour that hydrating message directly into the audience’s hearts. I’m making your readers thirsty now, I can tell.
NLE: Turning 50 is a milestone that many performers approach with mixed feelings, yet you seem to be embracing it head-on with power and pride. What does “badass at 50” mean to you — personally and artistically?
DD: It means owning your story; every scar, every lesson, every triumph. It’s being comfortable in your skin, your body, your voice, your choices. I don’t feel the need to compete or compare anymore. As the kids say, I give zero fucks. And honestly? Fuck fear. Just do it.
I was talking to my publicist about this, how some actors still feel pressured to lie about their age, worried a casting director won’t hire them once they know the number. But why? Who cares? Age is just math. I know I look young for 50, so clearly, I’m doing something right.
Being a badass at 50 means saying, “Yes, I’ve earned this confidence, this wisdom, this joy — and I’m going to use it to light the
stage on fire.” And if you want to be there for it — hell yeah, let’s go.
NLE: The show is self-produced and staged at The Triad, a venue that has become a home to so many iconic cabaret performers. What excites you most about performing Sing Happy there, and what can audiences expect from these two nights?
DD: I chose The Triad because Sing Happy is more theatrical than some of my past shows — it’s got movement, storytelling, and a few surprises. This will actually be my first full show on that legendary off-Broadway stage, and it has everything I need: a dressing room right in the wings for my costume change, a stage big enough to play on, and that perfect blend of intimacy and old-school glamour.
The Triad has this vaudevillian sparkle mixed with real history, and I can feel it every time I walk in. Audiences can expect some sexy dance moves, powerhouse vocals, a few dark twists… and maybe a tear or two. Mostly, I want people to walk out feeling lifted — reminded that no matter your age, you can choose to be bold, be honest, and Sing Happy in life.
NLE: You’ve been praised for making “each song into a one-act play.” How do you approach interpretation — what’s your process for finding the dramatic truth inside a lyric, especially when revisiting songs audiences may think they already know?
DD: Oh, I forgot about that quote — truly, that’s what every vocalist or performer dreams of hearing. I’d love to say it’s all me, but I’ve been taught carefully how to shape my craft to deliver that “one-act play” in a song. Every lyric has a secret underneath it, and to find it, you have to ask why — and who you’re really talking to. I dig until I find that heartbeat.
I never sing a song the same way twice, because neither I nor the audience are the same people we were yesterday. That’s the beauty of cabaret — the truth evolves right there in front of you. And that’s where the magic happens: when you stop performing and start living the lyric. That’s the sweet spot I chase every time I walk onstage — to make the audience feel something real, to hold up a mirror and say, see? me too.
