Desi Oakley

📷 : Joanna DeGeneres

After touring as Jenna Hunterson on the National Tour of Waitress the Musical, Desi Oakley was called back to the show earlier this year to play the lead character in the West End production to cover cast illness, which saw her make her West End debut. Last year, Desi played Roxie Hart in Chicago on Broadway, and amongst her many other stage credits, she has appeared in Wicked, understudying a number of roles including Elphaba, played Princess Fiona in Shrek the Musical and was Alternate Eva on the Evita National Tour. Desi is also a singer-songwriter, and during the shutdown of Broadway, she has released her latest EP Pocket of Time, with donations going to Dramatist Guild Foundation. Along with her career, Desi also teaches, and in 2019, she started Pop Rock Broadway with fellow actor Krystina Alabado. We recently chatted with Desi about playing Jenna in Waitress the Musical on the National Tour and in the West End, joining Chicago last year as Roxie Hart and releasing her new EP Pocket of Time.

You played Jenna on the National Tour of Waitress the Musical, what do you enjoy most about this role/show and how did the tour go?

I loved playing Jenna! I love the music (written by my singer-songwriter idol!). I love that the show is grounded, real and raw. I loved playing a character that everyone can see themselves in. I learned a lot by leading the company on tour and travelling at the same time. It was a time of my life that I’ll always cherish.

How does it feel telling Jenna’s story and seeing the audience reaction throughout the show?

The audience reactions were different in every city we went to – and that was one of the most rewarding things to experience. The show took on different shapes and the way people responded actually fueled my show. I heard people sniffling during the emotional parts – I heard people gasp during the shocking parts – and I heard people giggle along with me at the silly parts. During the solo parts, the audience made me feel less alone on stage. It felt like we were all humans going through the story together.

You were called over to London for the West End production earlier this year, what was this like and how was it getting back into character for your West End debut?

Flying to London to play Jenna in the West End was incredible! It was entirely unexpected, and the process was such a whirlwind! It was overwhelming to know it’d been a while since I’ve played Jenna, but I slipped back into character easily – especially with the supportive cast and crew holding me up. My Jenna was so grounded, because I was so in the moment, and appreciating every single second of it.

📷 : Joan Marcus

How did you find your time in London?

I absolutely loved being in London. The city is so electric – it’s a different vibe than NYC. There is so much history and life tucked in every street corner – the people are posh (a word I learned to appreciate there!) but they’re also friendly, polite and matter-of-fact. I loved the food, the architecture, the people, the whole vibe. TAKE ME BACK!

Last year, you appeared in Chicago on Broadway as Roxie Hart, how was this?

The Broadway production of Chicago is every bit as alive as it was twenty-four years ago when it opened. Roxie was one of the most fun characters I’ve ever played. I’ve never had so much freedom onstage than I did playing her – the music, the orchestra on stage, the storyline. All of it made me come alive each night. And let me tell you: the music does not get old. The second you hear that trumpet opening and the conductor say “a-five, six, seven, eight!” – there’s a pulse in your veins that doesn’t stop until the curtain comes down.

Can you tell us about touring as Alternate Eva in Evita?

I’d love to tell you about that blissful time of my life! I travelled the country as the alternate to not only the leading role in a huge National Broadway Tour, but also with my best friend, Caroline Bowman. She booked the role of Eva Perón months before I knew I was joining and we celebrated, having no idea that I’d be leaving with her a couple months later. We launched the tour side-by-side and fully supported one another. The producers were always pleasantly surprised – as this was one of the first positive relationships between an “Eva” and her alternate (as you can imagine). I loved the role. I loved doing it twice a week. I loved the downtime – because I wrote my first EP during all of those performances when my best friend was killing it. We told a beautiful story and still came out even closer on the other side. Eventually we went on to do other contracts together as well. Life is beautiful sometimes.

What do you remember from making your Broadway debut in Wicked?

I was so excited and nervous to join such a long-running, successful blockbuster Broadway show as my debut. I wanted to please everyone. I had very high expectations of myself. And I was a perfectionist. All of these things I’ve learned to find balance with since then! However, joining a huge show like Wicked taught me everything I know now as a professional artist. Respect for every role – onstage and off, quality of performance, surrender, gratitude, work ethic, being a part of a big business operation, finding my voice and being a team player. I went back for several more contracts after that because they are loyal and continued to employ me, while allowing me to explore other roles in the show. I am indebted to Wicked.

You’ve performed in many other shows including Annie, Shrek the Musical and The Prince of Egypt, can you say more about some of them?

After my debut in Wicked, I left the show to join the Broadway revival of Annie and it was such a rewarding experience. Building a show from the ground up (even a revival) is such a beautiful, inspirational (and stressful!) process that I feel lucky to have been a part of. While I was starting to play more leading roles, later in my career, I took opportunities at regional theatres to get more experience with different leading roles. Playing Fiona in Shrek was one of those times. It was a short contract in Connecticut but the payoff was great. I learned that I had some comedic chops that I’d been hiding for a while, in effort to preserve my ingenue appeal. I think that freedom with comedy onstage really helped in my later portrayal of Roxie Hart. Everything has its reason!

📷 : Jeremy Daniel

Can you tell us about your latest EP Pocket of Time and how long were you working on it?

I was so excited to release Pocket of Time – it was always my intention to release it around April, but it happened to have gotten done after the shutdown of Broadway. I released it anyway – with an intention to support other artists, with a donation going to Dramatist Guild Foundation. I wrote the entire thing in six weeks. It’s simple, real, and not over-produced. Just me and my instrument speaking my truth. I am the most proud of it out of all the albums I’ve released.

Where do you get the inspiration from for your songs and what’s your writing process?

Sometimes I write about my own experience, other times I write about other people’s experiences or stories. I get inspiration for my songs everywhere — through other people, through other forms of art, and sometimes even in my dreams. I love writing music. It’s therapeutic and healing for me. It’s my way of freely expressing myself.

Was there anything that encouraged you to start releasing music and what was the response like to your previous releases – Repeat and Don’t Look Back?

I was encouraged to write music by my loved ones, after they heard my first song Don’t Look Back from the EP of the same title. I got such positive feedback after performing the song for a cabaret in Los Angeles during Evita. So I continued to write more, going on to release the EP and later the full album Repeat. I love sharing my music. I always appreciate when someone says that my songs have inspired them or helped them. It’s one of the most amazing gifts.

Had you always known you wanted a career in both music and acting and how did you get into them?

I’ve always written music, and I’ve always loved to perform. I decided at age sixteen to pursue musical theatre – but at that time in high school, I was deciding whether I should do that or study songwriting and move to a city like Nashville or Los Angeles. With full pursuit of Broadway, my instinct to write was still strong. It wasn’t until my Broadway career made a little room that I was able to intentionally write with the hopes to release music. I am so proud to say that I’m able to invest time in both songwriting and performing. Both are so important to me. And both of them play such a huge part in my artistry as a whole.

Which music artists do you usually listen to?

I love all types of music – from Top 40 to singer-songwriters to rap to jazz (Fun fact: the only genre of music I don’t listen to is musical theatre!). I am inspired by artists like Sara Bareilles. I’m inspired by artists who write honestly. I think a good song makes you feel something. It doesn’t have to make you weep. Even if it makes you tap your foot, that’s enough for me.

What have you been up to while theatres have been closed?

Since the shutdown, I’ve been able to continue to invest in my students, most of whom I’ve coached virtually for many years. Now that I have time, I’ve been able to expand to almost a full roster of virtual students. I teach voice lessons, I offer business coachings, teach masterclasses and do Q+As. I love working with aspiring artists. I started a company last year with one of my best friends and Broadway colleagues, Krystina Alabado. It’s called Pop Rock Broadway. We teach pop/rock technique while talking about the importance of being your unique self in the business as a whole. We’ve met so many young people over the months. I’ve felt very grateful that this happened during a time when connection is still possible online. I am still connecting through my artistry, I’m still writing, and I’m still hopeful that we can come out of this stronger.

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