Desi Oakley is currently baking pies around the US as Jenna in Sara Bareilles’ hit musical Waitress. A talented performer with a beautiful voice, it is no surprise that her stage credits do not stop here: she was previously seen on Broadway in Wicked, Les Misérables, and Annie, understudying much-coveted roles such as Elphaba and Fantine. Desi recently took some time off her busy schedule to chat with me about playing the lead in the National Tour of an incredibly relevant and heartwarming show.

How has it been being on tour?

It’s wonderful. Tour has been so great and so much fun, and LA is such a cosmopolitan and gorgeous city. I love it here!

For those who don’t know Waitress, can you explain a little about the show and your role?

Yeah! It’s the story of a small-town pie baker who is in a loveless and abusive marriage, and she sort of bakes her fears into her pies. It also talks about her place at the diner she works at, and how the owner of the diner and her doctor eventually open up her eyes to reality. 

You’ve had a very varied and extensive career. What are some highlights so far?

Well, I loved being in the cast of the revival of Les Misérables. I loved working with little girls in Annie on Broadway. I’ve had the opportunity to play Elphaba on Broadway. And of course Jenna has been a huge career highlight for me.

Waitress is a pretty new musical, but it’s already garnered a huge fan following. What do you think makes it so special?

I think the story is so relatable and down-to-earth, and there’s just something in the story for everyone whether or not you enjoy musicals. It’s a very important story to be telling right now because it’s about strength, especially in terms of women. And there’s so much humor and heart in the show that it’s hard not to love.

Are you as good a baker as Jenna?

No, I’m nowhere close. I’m a New Yorker so there’s a lot of Uber Eats in my life, but I do try to cook and bake at home. I really enjoy cooking and I make a mean chocolate chip cookie.

What’s your favourite kind of pie?

I have a lot of favourites, but I tried some really good old fashioned pie in Milwaukee that was by a local baker. It had custard and tart cherries on top, and it was just perfect.

Jenna is such a strong female character. Why do you think it’s important to tell her story?

With the current climate and looking at how society is right now, I feel like women are finally finding their place at home, in their workplace, and even in their digital lives, and I think a story like Jenna’s is really appropriate. And no matter what, both women and men draw their strengths from what they see – from people like Jenna, and I think people are seeing her strengths and then translating it into themselves and their own lives.

What’s your favorite song from Waitress and why?

I love them all, but I always love “A Soft Place to Land.”

Are there any onstage mishaps you can tell me about?

There’s a lot of food that goes everywhere. In “What Baking Can Do,” I slam a rolling pin onto a cutting board, and there was one show when the handle of the rolling pin hit a bowl of cherries, and they just went wild. They were all over the stage, so people were picking up cherries throughout the show. We get used to working and performing with food though: it ends up being just like a normal job. I like working with real food and all that because it really keeps me in the role.

If you had a choice, what show would you do next?

Millie in Thoroughly Modern Millie. 

Do you have any advice for aspiring performers?

You know, I get this question a lot. I feel that if young aspiring performers have a dream to do this, if you feel like there’s no other choice but to pursue this, then you must. Because your gut is probably right – mine was, and the idea of getting to constantly grow and constantly learn is amazing and so important. Make sure you know both your strengths and weaknesses, because if you acknowledge your weaknesses, you can then be like, “Ok, this isn’t what I do perfectly, but I can either be crap or focus on my strengths.” You have to find all this out by yourself so that other people aren’t defining this for you. Also, just being kind and working really hard will get you a very long way.