Chicago Star Desi Oakley Talks 'Painting the Sky Bright Red Roxie' and Her Favorite Pie

The name on everybody's lips is going to be Desi Oakley, who has joined the ranking of women who have led Broadway's Chicago as Roxie Hart. Oakley stopped by Broadway.com's #LiveAtFive to talk to Ryan Lee Gilbert about stepping in to the long-running musical, her time on the road with Waitress and more. "I find it fascinating that the show is not only still playing but is still crushing it," she said. "There are still audiences going absolutely insane for this because it's just so good. Being a part of something that is so much bigger than me is iconic. The stories behind the women who have played these roles, and the stories that they told, and where the show has come from and how far it's come is really unbelievable. It's humbling to be a part of it. Honestly, it's amazing."

Although Chicago is Broadway's second longest-running show, Oakley is finding new ways to make the character her own. "When the opportunity presented itself to be considered for Roxie, especially after doing a role like Jenna [in Waitress on tour], it was a little shocking to me," Oakley said. "My spirit is a lot more like Roxie. There is something about her spunkiness and about her fervor and drive and gumption and her absolute desire to perform. There's a moment in the song 'Roxie' where there's this vamp, '♪ Doop, doop, do do do do do ♪' that I've totally played with. I was taught to paint the sky with my hand and I think of the movie, that bright red Roxie. I see it as big as The Ambassador and I see her name R-O-X-I-E and I grab it. That's the most rewarding part. I absolutely am obsessed when someone's like, 'Oh, no one's ever done that.' I'm like, 'They haven't? Oh my gosh, I'm the first person in 23 years?' It's so cool and I feel such gratitude."

Before stepping into the Cook County Jail, Oakley was giving the country a taste of pie as Jenna in the first national tour of Waitress. "It was almost a year and the role taught me so much," she said. "I realized a lot about myself because sometimes it would just be me and Jenna on stage. The biggest thing I'll take away from it is that balance is important and that I'm human. As much as I want to always give 110%, it's okay if you show up tired. Playing that role and having that opportunity was like a mirror in my face. It helped me grow."

Of course, playing a pie-baking waitress means that Oakley had her fair-share of the delicious dessert. "I'm obsessed with pie," she said. "[In Milwaukee,WI] they served Old Fashioned pie in the lobby and it was hands-down the best pie I've ever tasted in my life. Think of an Old Fashioned drink with bourbon and custard and cherry. The best."

Oakley has made appearances in both Waitress and Chicago within weeks of each other, so we had to ask what would happen if Roxie and Jenna were to meet. "Roxie Hart would find herself in Joe's Pie Diner if she got into a lot of trouble and was on the run," she said. "She would order the Razzle Dazzle Raspberry Pie, or maybe the Cellblock Mango Pie."

Catch Oakley in Chicago through September 8!

Watch the full #LiveAtFive episode below!