I am so excited to be catching up with Singer, Actress & Producer Dawn Derow. I last spoke with Dawn in 2021 when, after a year of no performances due to the worldwide pandemic, Dawn was finally able to return to the concert stage & debut her new show, Gypsy In My Soul: Dawn Derow Sings Eydie Gormé. 

On the heels of Dawn's 50th Birthday coming up, she is about to premiere her latest cabaret show, Sing Happy which celebrates the powerful women of Kander & Ebb musicals.

In this NEW interview, Dawn once again answered my call, but this time around she shares:

• What made now the right time to present Sing Happy
• One reason audiences should come see her new cabaret show
• How she is living her life with unapologetic fire
• Getting through her biggest loss
• So much more

Connect with Dawn: Website, Facebook, Instagram

Sing Happy is a bold celebration of Broadway’s most unforgettable women, brought to life through the music of the legendary songwriting duo John Kander and Fred Ebb. Sing Happy is an evening of passion, panache, and poignant storytelling that celebrates Broadway’s boldest broads and the timeless brilliance of Kander & Ebb.

Direction by the award-winning David Sabella (Chicago), choreography by Jason Reiff, and the masterful talents of Music Director & Arranger Ian Herman (Grease) at the piano.

Dawn takes the stage at The Triad in NYC on Tuesday, November 18, 2025 & Monday, December 1, 2025 at 7pm. Click Here for tickets! (Doors open at 6:30 p.m.; two-drink minimum required per person).

Special guest appearances will make each performance a one-of-a-kind experience: Aisha de Haas (Bring In Da Noise, Bring In Da Funk, RENT and Caroline, Or Change) will be featured on November 18th, while 10-time MAC Award-winning Broadway actress Karen Mason (Mamma Mia!, Hairspray, Sunset Boulevard, And the World Goes 'Round) will join Dawn on December 1st. 

1. This November & December, you are presenting your new, self-produced cabaret show, Sing Happy, at the Triad in NYC. What made now the right time to present this show? Well, I figured if Liza and Chita kept reinventing themselves during the height of their careers, why shouldn’t I? Sing Happy is really a celebration of that — strong, complicated women who live loud, love hard, and sometimes make a glorious mess of it all. I feel and identify with all the above!!

Timing-wise, I wanted to take more risks in my performance art and to be bolder. In my 20s, I was a dancer; over the years I shifted into being a “singer who moves.” So for this NEW show, I wanted to challenge myself and dive back into learning choreography and reconnect with that physical side of performing.

We created something that feels alive, spontaneous, and true to where I am right now and where the world is. After the last few years, I wanted to put something into the world that reminds people — and myself — that joy and happiness are choices.

November also happens to be a big birthday month for me, which felt like the perfect time to celebrate with a little extra razzle-dazzle set to the music & lyrics of Kander & Ebb. And honestly, I think the world could use that too.

2. In Sing Happy, you are celebrating the iconic songs of Kander & Ebb as well as the powerful women from their Broadway shows. Why did you want to focus on their catalog of music? I started really working on this new project last winter. When I began putting the pieces together for the 2025 Cabaret Fest in Provincetown, MA (I’m from Cape Cod), Patricia Fitzpatrick has been working tirelessly for over 12 years to keep the Provincetown Cabaret Festival alive, and she asked me back in 2024 if I’d like to do a solo show for the 2025 season. When I heard that we’d be celebrating the music of Kander & Ebb, I practically jumped — and high-kicked — for joy!

From there, I knew right away that Ian Herman had to be my music director. And because I had just been in Puerto Vallarta performing a new show I created for David Sabella — who was then managing ACT2 PV — I knew he’d be the perfect director. David is a bit of a genius when it comes to the Kander & Ebb catalog. In case your readers don’t know, David was the original “Mary Sunshine” in the Chicago Revival. Clearly I trusted his judgement completely: when it came to songs or shows I wasn’t as familiar with, he’d have incredible suggestions and insight.

To make it even better, my best friend, Jason Reiff, came on board as choreographer, which has been such a joy. Jason is like a walking musical theatre library, and between him and David — both of whom know Kander & Ebb’s body of work inside and out — they’ve been whispering brilliant ideas in my ear. Together, we’ve shaped this show into a celebration of the extraordinary wonderful women and unforgettable characters brought to life by Kander and Ebb musicals.

Dawn Derow
Photo Credit: Joe Navas

3. What was the first song or character that sparked your interest in creating Sing Happy? That one’s easy…the spark was always Sally Bowles and her iconic number, “Don’t Tell Mama,” so that’s my Opening number.

Since childhood, I’ve been captivated by that character. I still remember listening to my father’s 1966 yellow-cased LP of the original cast of Cabaret and falling in love with Sally’s wild, complicated spirit. Her story has followed me through every stage of life.

As a teenager on Cape Cod performing in tons of musicals, Cabaret being one of them, and throwing the occasional secret cast party in the basement, I was definitely a “don’t tell mama” kind of girl. But sometimes Mama Rose, my Mom, found out – oopsy!! She forgives me :)

In 2008, when I first ventured into cabaret as an art form, my very first “how-to” class took place at Don’t Tell Mama, taught by the legendary Lennie Watts and Lina Koutrakos. That was my “gateway” to the life of a “Cabaret Artist.”

And now I’m living just around the corner from Don't Tell Mama NYC (Shout out!) a full-circle moment if there ever was one. Although, don’t get confused, the show will actually take place at the off-broadway Triad theater - which will be the first time I’m doing a full show there!! Did that answer your question while also referencing enough shout-outs to my community?

4. What is one reason audiences should come see Sing Happy? So if you are a fan of my many shows - I’d say you will see yet another side of Dawn Derow - maybe more fiery, more daring, more shocking, and more vulnerable for sure.

If this is your first show of mine - I think you will hear a catalogue of tunes you can relate to, some familiar some maybe not, but mostly, I think it’s clear the fascination of these two men John Kander & Fred Ebb - who wrote such feisty characters and songs for women - back when it maybe wasn’t such a popular concept.

Like I say in the show - they were way ahead of their time! As a side note; there is one male character song on the set list, but the lyrics were too perfect to skip sharing just a portion of it. Come to the show, and see if you are able to pick it out.

Dawn Derow
Photo Credit: Joe Navas

5. According to press notes, the female characters you are honoring in Sing Happy have lived, loved, lost, and triumphed with unapologetic fire. I am going to break these subjects down into a few questions.

• How do you feel cabaret makes you truly live? Authentically - there is no other way. It’s very apparent in my personal life right now and that translates onto the stage for me. There is no way around it. You can’t hide your truth! Of course, I’m a good actress too but all that has to come from some place real too.
• What is the greatest love you have experienced? Wow! That’s a big question disguised as a dozen little ones! Love comes in so many forms; romantic, creative, cosmic. But if I’m being honest, the greatest love I’ve experienced is SELF-LOVE! As a singer, my instrument literally lives inside my body. If I don’t care for and love that body (and the soul that powers it) I lose my voice, both literally and figuratively. So learning to love myself has been the ultimate romance. And let’s be real… that love story takes work. Some days it’s a full-on duet with my demons. But it’s the one relationship I know I’ll have for life.
• How did you get through your biggest loss? So now this seems to ask about a relationship with the opposite sex.. I have had many losses in that department. Still do! So I have to say what gets me through is music!! Every time! Usually my go-to is the profound lyrics of the Indigo Girls or Sarah McLachlan or nowadays I’m really liking the song stylings of Sabrina Carpenter.
• What do you feel is your biggest career triumph? A few months ago, I got to play my dream role — Francesca in The Bridges of Madison County at the Delray Beach Playhouse. We did twelve shows over three weeks, received standing ovations every night, and I was honored with the Del Lago Award for Outstanding Actress. That role was deeply personal to me. Francesca is Italian American, and my own grandmother — my Nonna Rita Benvenuto — came to this country from Calabria on a boat that left from Napoli… which, coincidentally, is the first line of the show. So much about Bridges just lined up perfectly. Jason Robert Brown’s score let me soar in my legit soprano voice, and I got to embody Francesca’s Italian accent with love and authenticity. My scene partner, who played “Robert,” Colin Salvatore, was extraordinary - who I am sure will be on Broadway in the coming years. And my family unit; my husband “Bud” and my two stage children, they were wonderful to work with. Honestly the whole cast held me up like the pillars of “a bridge.” I hope I get to play her again!

Dawn Derow
Photo Credit: Joe Navas

6. As someone who also just turned 50 this year (I know you are about to), how do you feel you are living with unapologetic fire now as compared to earlier in your life? Well, every one of my friends who’s already in their 50s says it’s the “zero fucks given” decade. Pardon my cursing — but honestly, there’s a lot to curse about these days.

I’ve spent too much of my life being nice. No regrets, but looking back, there are definitely moments when I think, “Wow, I wasn’t bold enough because I didn’t want to stir the pot.” Well, that pot’s boiling now. Time is of the essence. Life is short. Fucking go for it. Make a splash. And if it doesn’t work out? Zero fucks.

One of my girlfriends always says, “Dawn leads with love.” And it’s true — I do. That’s the energy that draws people into my orbit. But these days, I also come with a warning label: you might get a fireball thrown your way, too.

After all, I’m a Sagittarius with a Leo Moon and Aquarius rising — love first, fire second, originality always ♐️🔥

7. In addition to performing this cabaret show, you are producing it. What do you do as the producer of Sing Happy that you wouldn't be doing if you were just singing in the show? What don’t I do!! We do everything.

But actually for this show and my last show Women’s Work, I hired a publicist - Beatrice Kimmel of EMPKT Media Inc. - (Shout Out!) which is a big expense, but it’s just so challenging to work on the show as the artist, the writer, the creator, the singer, the dancer, the props manager, etc. and also get butts in the seats.

So the producer in me is saying to your audience right now, “If you’ve read this far, click on the link above and buy tickets now!!”

Dawn Derow
Photo Credit: Joe Navas

8. In addition to producing your own cabaret shows - I notice you are also the co-producer of a new musical in the works? Yes - 3 years ago I jumped into the seat of co-producer for a Carnegie Hall presentation of the songs for a new musical.

And today, I am happy to say I’m still co-producer as well as a member of the cast for the new musical about Dorothy Dandridge’s life. The working title is Spotlight.

We just completed a staged 29 hour industry reading at the Laurie Beechman this week - I’m playing the role of real life gossip columnist: “Hedda Hopper”

We are happy to announce that we have our first out of town run at the Axelrod Performing Arts Center in Feb/March 2026.

9. What is something we didn't get to talk about in this interview that you'd like my audience to know about you? Well, aside from performing, I’m still very dedicated to my wellness work — I teach Mobility and Stretch classes (especially for the 55+ crowd) and offer Thai massage and bodywork sessions for my clients.

Staying fit and mobile as we get older is VERY IMPORTANT. For myself, I regularly work with a kettlebell coach to keep fit, strong and balanced. So as a certified trainer, I get the importance of having a trainer.

If anyone’s interested, my online Mobility Class is a fantastic way to keep moving and feeling great — it’s just $25 on Zoom and open to all levels. Shoot me an email at [email protected] - and I’ll send you all the info.

So for anyone reading who might need a little more flexibility or motivation, I’m happily taking on new clients now that I’m back in NYC more regularly.

I’ll be spending more time in New York City this year (with a few Florida gigs in December), and I’m also looking for new representation — a manager and agent — so I’ll end by being bold and putting that out there! (It’s my Birthday Wish).

More Dawn Derow Interviews:

2021 (Read Here): Gypsy In My Soul: Dawn Derow Sings Eydie Gormé
2018 (Read Here): My Ship: Songs From 1941

Dawn Derow
Photo Credit: Michael Kushner

More on Dawn Derow:

Dawn Derow is a New Yorker by way of Cape Cod & has been captivating audiences for more than 17 years with extraordinary versatility, moving seamlessly from Puccini to Brandi Carlile, Broadway to jazz.

A graduate of The Boston Conservatory, she has performed on world-class stages including Carnegie Hall, Jazz at Lincoln Center, and London’s Pheasantry, as well as leading New York City venues such as 54 Below, Birdland, The Green Room 42, and The Laurie Beechman Theatre.

Beyond New York, she has headlined nationally at the Dakota Jazz Club, Café Centro, Mohonk Mountain House, and Provincetown’s Post Office Café, and appeared with the Cape Cod Symphony Orchestra.

Her artistry has earned her three MAC Awards (including Best Female Vocalist and Best Album), a Bistro Award, and glowing reviews for acclaimed shows like Revolution, Legit: A Classical Cabaret, and My Ship: Songs from 1941.

Her album My Ship won Best Album at the MAC Awards, with Cabaret Scenes hailing her as “a supremely accomplished artist” with “a remarkable range.” Her acclaimed tribute, Dawn Derow Sings Eydie Gormé (played both at Birdland and 54 below, NYC), was praised for its vocal fireworks and recently played to packed houses, cementing her reputation as one of cabaret’s most versatile performers.

Equally at home on the theatrical stage, Dawn has starred as Antonia in Man of La Mancha, Cathy in The Last Five Years, Adele in Die Fledermaus, and most recently Francesca in The Bridges of Madison County at the Delray Beach Playhouse, a performance that earned rave reviews and the award for Outstanding Actress in a Mainstage Production (2025).

Internationally, she has brought her cabaret artistry abroad with sold-out runs at London’s Pheasantry (My Ship, 2023; Women’s Work, 2024) and a recent premiere of Because I Can/Porque Yo Puedo in Puerto Vallarta, Mexico.

Expanding her creative reach, Dawn co-produces Dorothy Dandridge: The Musical and originated the role of gossip columnist Hedda Hopper in its workshop.

Offstage, she teaches mobility classes, provides Thai massage, and supports older adults in wellness programs. She divides her time between New York and Florida, returning to Provincetown each summer to perform.