On The Road: Desi Oakley
Today's On The Road interview is so special because this girl is one of my favorite people I've gotten to know during my time on Broadway, and I am extremely excited to introduce you all to my sweet friend Desi Oakley! I first met Desi backstage at Wicked in 2015 when I was still a swing dresser. I was immediately blinded by her megawatt smile, and she bear hugged me the second we were introduced. She is one of those people that just genuinely exudes sunshine because she chooses joy every single day. One afternoon, she gave every single member of the Female Ensemble (including the dressers) a daisy because it was National Daisy Day and she wanted to make everyone smile. I am so thankful for Desi's friendship and inspired by the way she lives her life.
Desi is currently starring as the lead character Jenna in the first national tour of the hit Broadway musical, Waitress. I was able to set up a photo shoot for her while the show was in Des Moines, Iowa, with the phenomenal local photographer, Sam Fathallah. I am obsessed with these pictures and her heartfelt interview. Hopefully, some of you will be able to see Desi as she travels across the country with Waitress, but if you can't make the show, you should definitely check out her solo album! (My favorite song from it is White Butterfly.) Anyways, I just know you all are going to love her as much as I do.
How long have you been a performer?
I’ve been performing since I was 8 years old. I began as a professional at 14. I’ve been paid to do what I love ever since.
What is your favorite show you've ever worked on?
Not to be cheesy, but it’s definitely WAITRESS. This show is so insanely special, and launching the tour was a big challenge that I feel proud to have tackled.
Who is the coolest celebrity you've ever met at work?
I worked with Jane Lynch on ANNIE, and she was the epitome of “cool.” After I made my debut as Lily St. Regis — a character sharing the stage with her often — She was standing in the wings as I exited, and she said, “Oakley, you’re Broadway, baby.”
What is the most interesting day at work you've ever had?
My Broadway debut. WICKED. I didn’t sit down for the entire show. (the ensemble has close to a 30 minute break at one point), and as the curtain rose (I was shaking violently with anxiousness) everyone around me was debating whether regular or double stuffed oreos were better. I’ll never forget it.
What is it about this job that makes you come back each day?
I call it “theatre magic.” During a stage performance, there is a connection present that doesn’t exist anywhere else. Between actors, between audience and actors, among the backstage bustle. There is simply nothing like it. And I can’t get enough.
What is your favorite thing about your job?
Telling this story and connecting with audiences who have never heard it. The story affects me every night, (salty tears in my mouth, and snot running everywhere) and I hope it makes an impact on them, too.
What is the most challenging part of being an actor on tour?
There are so many factors about traveling and preparing for a show. Plane ride: other passengers, stuffy air; Hotel: heat/AC is dry, uncomfortable bed; Long travel days: unexpected delays, traffic, general exhaustion from changing cities, the list goes on. It’s about accepting your surroundings, and finding your constants.
What is the most surprising part of your job?
How the cast can come together to change the environment. As previously stated, the road can be rough. But after a laugh with a castmate, or an encouraging conversation can turn the entire day around.
How long do cast members usually stay on a tour?
It depends! Some principals stay up to a year, ensemble members usually sign a 6-month contract and then have an option to renew.
What are some items you absolutely can't live without backstage?
Throat Coat tea, water, my Purmist, and little trinkets I carry with me to each city: my daddy’s old horseshoe, a rose quartz (promoting self-love), a photo of my mom’s hands teaching me to bake a pie (to inspire my character), a hand-written card from Sara Bareilles.
What's a random fact about touring that people are always surprised to learn?
It’s almost always a 5-show weekend, and we pack up Sunday night after the show and have another show in another city on Tuesday night. The turn-around is unbelievable. The crew goes ahead of us, and prepares, but we sound-check in every city and adopt a completely new house [sometimes] every week.
What has been your most memorable moment on this tour so far?
The most memorable day on tour so far was our opening night. I had drinks with Sara Bareilles and she told me that this role was perfect for me, and that she was so pleased with my performance. It can’t really get better than that. On days when this feels difficult, I remember that moment.
What is your favorite part about telling this story every night?
This story changes the way people see life and especially see themselves. It is powerful to tell a story that can shape people. There’s a responsibility I feel in my work that I’ve never felt before, and it really inspires me.
What advice would you give to a young person who wants to move to NYC and pursue a career in the arts?
Be kind. Always! It is truly the reason I am where I am. Talent is great, but more importantly, the more people WANT to work with you, the more you will work. The best way to get into this industry is to TRY. Dream it, and then do it. Move to NYC, meet people, audition, take class, soak up people’s experience/knowledge, try and fail, try again, hear “no” and then KEEP GOING. If you want this bad enough, nothing will stop you. It will look different than you planned it, but at least you had a vision. You HAVE to try to know anything.
What piece of advice would you give your 18 year old self?
It will look different than you imagine right now. But remain open-minded while you keep working hard. Every single “no” is creating space for so many “yeses.” And trust me. Your hard work will pay off. Keep going.
What is the best advice you've ever been given?
The best advice I’ve been given is to lead with kindness. Talent gets you far. Hard work gets you farther. But nothing will ever beat kindness.
FUN FACTS:
Where did you go to college?
University of Michigan, BFA: Musical Theatre
What was the first Broadway show you ever saw?
Beauty and The Beast, in 2000
What is your favorite Broadway show you've ever seen?
DEAR EVAN HANSEN or COME FROM AWAY
What is your favorite US city you've visited on tour?
Portland, OR or Denver, CO
What is your favorite costume you've ever worn or your favorite costume in your show?
The white, strapless Casa Rosada dress in EVITA [that is worn during “Don’t Cry For Me Argentina”] was pretty remarkable, it was close to $20,000. But my favorite costume in WAITRESS is the blue floral dress I wear in Act 2.
What's your favorite restaurant or bar you've found on tour?
On this tour so far, my two favorite restaurants have been in our first stop, Cleveland, OH: Lola Bistro and Greenhouse Tavern. We were there for 5 weeks, so I had enough time to get out and explore. There was a speakeasy in Kansas City that was super charming: called P.S. and the cocktails were wonderful. The best French 75 I’ve had in a long time. (my favorite cocktail!) Can’t wait to experience other cities’ eats!
Images by Sam Fathallah
Des Moines, Iowa
