What’s it like to be a musical theater understudy on tour? We go behind the scenes with The Great Gatsby cast
From the ensemble to the starring role—and what it takes to make it.
Photo by Matthew Murphy and Evan Zimmerman
The Great Gatsby is the sixth engagement in the ’25-26 “PNC Broadway in Kansas City” series, and will take the Music Hall stage March 17-22, 2026, for eight performances. Tickets are available for purchase at BroadwayInKC.com and Ticketmaster.
We’ve all been in the situation when we’ve had to cover for a coworker. Either they ate the “totally fresh” gas station sushi, needed to go on vacation, or broke a leg. Or worse yet, many of us have been given multiple roles in a company because they have let go of the entire department. But don’t worry, it was a business decision, and they are sure you’ll be a team player. We’re all family, except when it comes to a paycheck. Then you’re a distant cousin at best.
All of this sounds terrible, except for two specific niche professions. NASA astronauts and Broadway actors. Those among us who crave redundancy and are geared to pick up the slack to save Matt Damon on yet another pointless mission. Actors are prepared to do both, no disrespect to astronauts. But how many of them can save Matt Damian in song?
The Great Gatsby will be at the Music Hall from March 17 to the 22nd, and with them, the ensemble and understudies that are triple trained to make sure that the show goes on, even if someone was dumb enough to go for the sushi.
Kyle Caress
“We compartmentalize,” said Kyle Caress, who is the swing and dance captain of the show. These are two separate jobs. Well, technically, they are like eight jobs.
“It’s my job to know all the steps of every part, and maintain the integrity of the choreography,” Kyle added. And if one of the male presenting ensemble members goes down from the fabled broken leg, he must step in to cover. There are eight different roles that he must know. He does it all without going insane. Probably. He seemed pretty grounded when I talked to him.
“I have a lot of notes, and I keep a projector in my room with archival footage for reference. It helps me memorize those small steps, movements, or slight hand gestures,” added Kyle.
With Gatsby, there are twenty-seven cast members, and many will have multiple responsibilities.
Joann Gilliam plays Catherine, the sister of Myrtle Wilson. For those not up on your Gatsby lore, Myrtle is the mistress of the protagonist, Tom Buchanan. But that’s not the only role she has to prepare for. She is also the party singer Gilda Gray, which is great because Joann has the singing voice of the Greek Muse Calliope. On top of all that, she is also the understudy for Myrtle.
Which means she has to belt out the hits, know what Myrtle is thinking at all times, and then try to be a great fictional sister. Family is hard enough when there is no drama, but it’s often boring, and Joann is anything but that.
“I love the show, so it’s not hard to memorize everything,” Joann said. “It helps when I relate myself to the character in a way that makes sense to me. I make the character of my own.” Regardless of which part she is playing, it requires the ability to split your personality. They usually give people medication for doing that. But in Broadway, it’s encouraged.
“You have to be ready for on-the-spot changes,” Joann continues. “If someone sprains an ankle, you have to jump in and make it all appear seamless.”
The days of the ensemble and cast are spent on the road or at rehearsals, not only for their parts but for the parts where they are understudying. Which means that Kyle has to literally dance until he drops, and Joann needs to sing the same song over and over again. It’s one thing to shoot for perfection, and quite another for these two to acquire perfection for so many different roles.
There’s not a lot of free time to explore the cities they visit. When the curtain closes and the lights go out, they have to go back to work obsessing over details that the rest of us would never notice. They do get to go out occasionally. They like to try out restaurants, museums, and the nightlife. But being on the road for eight months or more can further wear on the performers.
The trick, according to Kyle and Joann, is to give your hotel rooms a touch of home. Pictures of loved ones, special pillows, or comfort items such as a favorite blanket. Kyle travels with a blender to make meals on the go, and Joann brings along a selection of teas and has a sunset lamp. Others may bring an air fryer to cook something quickly rather than go out to a restaurant or order Uber Eats. Each ensemble member gets a per diem to spend as they see fit.
It’s not all hard work, though, because at least they get the outfits. Those shiny and over-the-top costumes that sparkle under the spotlight and hug all the curves just the right amount. All of their costumes are made in New York, and it’s surprisingly detailed. There is the “feather guy” or the “bead guy” – the specialty shops that make Broadway a visual miracle. Joann has the largest wardrobe of any cast member. So, at least that sounds great, right?
“You have to remember that the costume is going to fit the exact way as when you were measured,” Joann said. That means if you went out a little too much or the DoorDash was a little too often, ensemble members will be stuffing themselves in a sausage casing.
With all that said, being on the road for a production such as this is a one-of-a-kind opportunity. It’s not so much about paying your dues as it is about living your dreams.
Photo by Matthew Murphy and Evan Zimmerman
“It’s fulfilling to find time to explore the cities that we are in. As the tour progresses, it’s some of my favorite times when I’m just a tourist in the city,” said Kyle.
This is Joann’s first tour, and she’s learning as she goes. Their initial stint was in Korea, which she loved. However, the road life can be hard.
“I’ve learned to be gentle and kind with yourself, especially during the long days,” Joann said.
Beyond the posters and marquee signs, the people who keep the show going are often the most overlooked. But if they weren’t there, the audience would notice. They provide the fantasy that we can all get lost in, and without actors and dancers like Joann and Kyle, the show wouldn’t go on.
