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Photograph: Chelsea Ross

Actor Sydney Charles’s path to the stage

Without a traditional theater background, Charles is forging her own career track

Written by
Kris Vire

Sydney Charles has seemed to be such a constant presence on Chicago stages in the past few years, you’d never guess how many times she’s tried to quit acting. If you’ve seen her embodying Dorothy in The Wiz, fighting crime in Jackalope Theatre’s Prowess or stealing scenes in Definition Theatre’s An Octoroon, you’d certainly never guess that she never studied acting in the first place.

Seven years ago, the Chicago native was working as a banker for J.P. Morgan Chase, saving money for law school. “I was bored with my nine-to-five. I was trying to figure out what I thought might make me happier than wearing that suit every day,” Charles says one afternoon at Steppenwolf’s Front Bar. “I started auditioning for things just as a hobby. I snuck in through musical theater, because I’ve been singing all my life.”

Charles pursued a prelaw program at Northern Illinois University after graduating from Kenwood Academy High School in Hyde Park. She later got a second bachelor’s degree in music education from VanderCook College of Music. “I started in church choir. My mom says I was singing before I could talk, but I don’t know if I believe that,” she says. (Like a lot of actors, Charles declines to give her exact age lest it limit the roles she’s perceived to be able to play. “I always say I’m old enough to drink but young enough to not have my AARP card.”)

Her first booking was a 2010 production of the musical Nunsense with the Saint Sebastian Players community theater. By the end of that year, she was performing in Cats with Theo Ubique. Charles eventually eased off of acting, not seeing a path to it paying her bills, but auditioned for Smokey Joe’s Café in 2012 as a favor to Cats director Brenda Didier. After another string of shows Charles backed off again, until playwright Ike Holter asked her to do a reading of his work-in-progress, Prowess. It ended up being her first nonmusical play.

After that, “I was like, I should just quit my job,” she says, laughing. “Headfirst, all in, no more Muggle job. I’m poor but I’m happy.”

This year she’s been steadily booked, with The Wiz, An Octoroon and the Inconvenience’s Fly Honey Show. This fall, Charles can be seen in Holter’s new play, Lottery Day, at the Goodman Theatre’s New Stages series, followed by the world premiere of Janine Nabers’s A Swell in the Ground at the Gift Theatre.

That doesn’t leave much time off, but Charles figures she’s still learning on the job. “Other people have been doing this for longer than me. I feel like I have to play catch-up, to not sit down. I want everything to hurt a little.”

See Charles in Lottery Day at the Goodman Sept 20–Oct 6 ( and in A Swell in the Ground at the Gift Theatre Oct 13–Dec 10 (

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