Chic Spotlight: Desi Oakley, Star of WAITRESS

Chic Spotlight: Desi Oakley, Star of WAITRESS

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We chat with the star of the Broadway musical WAITRESS and her co-star to hear more about the show and how she brought her character to life!

Cincy Chic: What are some of your favorite relatable aspects of the show.
Desi Oakley, Star of Broadway’s WAITRESS: Everything about this story is relatable! It’s a universal story where we zoom in on Jenna, who is just like everyone else. She’s not necessarily this dynamic woman that everyone is writing about, she’s the gal next door, so the people in her life are the guys and girls next door, too. So the script, a lot of it, is based on Adrienne Shelly’s screenplay, which is from the movie, and if it’s not those words exactly then Jessie Nelson, our book writer, has rounded the edges to make it more theatrical. But they aren’t too theatrical, they’re so relatable, they’re words we would all say in real life and not when putting on a character. So I would say that’s the best thing about the show, is it’s so relatable.

Cincy Chic: You mentioned the female power aspect of this, the creative team and everyone involved, and this is something that’s been celebrated by a lot of women because it’s one of the first times that all of the creative direction and everything is all-women. Not to mention Sara Bareilles, who is behind it as well and wrote the songs for this show. What’s your favorite song?
Oakley: My favorite song changes by the week! Because the music is pop music, it’s Sara. This week it is “A Soft Place to Land.” It’s a song I sing with my two besties at the diner, Becky and Dawn. And the three of us sing it and the harmonies are beautiful but at the same time it allows us to dive deep into this hopeful, dreamy state that we all want and desire deep, deep down. That’s my favorite song!

Cincy Chic: I have to tell you, and it’s not only the pregnancy hormones, but I lost it when you said “We were both born today.” And you kept a very good balance when you were singing that, this is the pinnacle moment and you’re holding the baby for the very first time. I never expected that when I had my very first baby and when you were singing it there was so much emotion behind it. Is that difficult to have so much emotion behind what you’re feeling?
Oakley: Thank you. You know that is a challenge, the best challenge for myself as an actress. I’m moved by this story as well. I tap into real-life emotions and experiences in order to tell Jenna. In that moment I think of my niece and nephew and the way that my sister has felt, and so I really am looking at this baby and seeing my nephew, the very first little baby I said I’m related to, and said there cannot be more love than this moment. And I am tapping into this. And I say that I would rather feel the emotion and crack on a note or it not be beautifully, perfect sung because I went there than to say that my performance was empty or without emotion, so thank you for saying that. That is a huge compliment to me and my work as an actress and I appreciate that!

Cincy Chic: We were talking about the relatable aspects: The motherhood aspect, the friends, the love, and also the mother. There’s a special relationship you mention throughout, the mother. Do you have a special relationship with your mom? Tell me about how she helped you prepare!
Oakley: So actually I had never made a pie before and when I told her about this role I was taking on she flew to New York City from Missouri to teach me how to make a pie! So she brought along a true recipe card of my great-grandmother’s cherry pie recipe and, in my studio apartment in New York, taught me how to make a pie. She taught me all these tricks and showed me exactly what to do. We did the lattice, a perfect, classic woven top and everything was just perfect. I remember that so much when I’m on stage and it was a beautiful moment and I’m just grateful to her for thinking of that. And for her it was just fun and I had no idea that it would really be in my muscle memory and in my vision as I’m painting a picture of Jenna every night.

Cincy Chic: You have some personal pursuits outside of Broadway, tell me about those!
Oakley: I consider myself a singer/songwriter. I’m very inspired by Sara Bareilles. I’m a classically-trained pianist. I’ve been playing since I was 8 and I studied really intensely for about 14 years, so all of my songs stem from piano but I kind of like to compare myself to Sarah McLaughlin nowadays, so kind of like a throwback, easy listening, nothing complicated, but you know, writing about life experience. I’m actually going to put out a second album after the first of the year!

Cincy Chic: So with Sara Bareilles on set during rehearsals, was it a very hands-on and involved kind of thing?
Oakley: She was like a mentor to me! She would say, because she played the role and wrote the story, she would give me tips about the apron and all these other bits of helpful information. She really took us all under her wing and I felt like she was so kind and generous with this process.

WAITRESS runs in Cincinnati from January 9-21 at The Aronoff Center. Learn more about the show and get your tickets at

Amy Scalia
Publisher & CEO - Amy Scalia, a Cincinnati native, is the editor in chief and publisher of Cincy Chic. Send her an e-mail at From growing up in the cornfields of Harrison and getting a Mass Communications B.A. degree in the bubble of Oxford, to living on the NKY side of the river in Newport and then Ft. Thomas, Amy Scalia has embraced Cincinnati with her presence. Her major life accomplishments include: being a mom of two girls and another little one on the way, a 2010 "40 Under 40" recipient from the Cincinnati Business Courier, winning the "Best New Product/Service of the Year" Award from the Cincinnati Chamber of Commerce and a national Web-writing award from ASHPE in 2007, a national feature writing award from ASBPE in 2006, and running three Flying Pig Marathons.