Broadway actress and singer-songwriter Desi Oakley is over 200 performances in on the national tour of the fan-favorite musical Waitress, now at The National Theatre.
She plays the lead role of Jenna, a small-town diner waitress who transfers her dreams of escaping her loveless, abusive marriage into the creation of wonderfully creative pies in the touring production of Sara Bareilles’ hit Broadway musical based on the popular 2007 film.

Oakley made her Broadway debut in 2003 as an understudy and replacement in the cast of Wicked and appeared in the 2012 revival of Annie and the 2014 revival of Les Miserables as well as the 2013 national tour of Evita as an understudy and alternate performer in the title role. She’s also a musician, released a six-song EP, “Don’t Look Back” in 2014 and is currently working on a new album.
Oakley discussed her starring role and the national tour of Waitress with DCTS:
In what ways have you been able to identify as Jenna?
We’re similar in a lot of ways and different in others. She is from a small town and I was born in Wichita, Kansas. I can relate to her being a dreamer and wanting more for herself. Everybody has desires and hopes for themselves and her dreams are a big part of who she is. But the big difference between us is that she is more or less stuck in a lot of ways and cannot fight for some of her dreams, where I’ve always been fighting to be where I am at and performing.
What has the response been like in the cities you’ve played so far?
The audiences have been unbelievable. They come in excited if they’ve heard anything about the show. And then they leave ecstatic, because this show is special. It is so well written, so important in this climate. It’s not just about fighting for your dreams but standing up for yourself and loving yourself. Audiences really connect with it. Not to mention the music is so easy to listen to and Sara Bareilles’ score is just beautiful. It’s so fun to sing every night, it never gets old.
We hear from people who are also hurting in the way that Jenna has been hurt. Maybe that means physically or emotionally abused, or stuck in a relationship where they aren’t thriving, there’s a lack of love, and that is the biggest reminder that there is a purpose for this show.

How would you describe the music?
Sara Bareilles has her tone all over this. It’s a pop score and so laid back. Every song sounds like it could be on the radio. Songs ease in and out of scenes seamlessly, unlike a lot of musicals, where the orchestra starts in. This is more like the guitar starts strumming, we go into song and then we’re singing and the audience hardly realizes it’s happening. The transitions are so simple and seamless. It keeps audiences engaged in the purpose of the story. The music furthers the plot and story big time.
Did you find any similarities with your own style of music that you apply to the show?
Absolutely. I have a similar style to Sara, as a piano-based singer-songwriter. I think that’s a huge reason why I was picked for the role.
What’s the hardest part of playing this role for you?
The most challenging thing has been to separate myself from Jenna. Because I draw on my personal life as an actress, to maintain eight shows a week for seven months can be exhausting because she goes through so much in the show. I often have to separate myself from her just so I can go home every night and be me. It’s challenging, but it’s also very rewarding to play a “real” person, and someone feels the things she does.
How many pies do you whip up on stage, and which is your favorite?
I technically bake two or three but I mention the recipe for close to 10. Jenna varies her pies based on the problems in her life. I really love the way she describes Getting Out of the Mud Pie. It’s when she starts to picture her life moving in a positive direction. That pie represents a turning point for her. That’s one of my favorites.
[We’re hoping the cast will get the chance to sample our local Dangerously Delicious Pies]
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