Meet Sydney

photo by Alexus McLane

“…necessary lesson in history and humanity laced with sugar to others. The cast, a blend of Chicago stalwarts like the always-outstanding Sydney Charles…”

Brien Hieggelke - NEW CITY CHICAGO

“…played by Sydney Charles, who endows this largely quiet, patience-worn feminine spirit with a finely honed stubborn streak. […]she delivers patent-worthy silent glares…”

- Nancy Malitz - Chicago Sun-Times

“Charles, who plays the much bigger role of Shug Avery in the rising director Lili-Anne Brown’s new production, is one of the experienced anchors in what mostly is a young cast at the Drury Lane Theatre. Charles, centered and complex as ever…”

- Chris Jones - Chicago Tribune

“Charles… is remarkably well cast in director Kenneth L. Roberson’s production. She doesn’t, as would some, have Ronnie Scott’s veneer to shake off. On the contrary. She is naturally intimidating and goes right to where Simone would have been in that moment. “

- Chris Jones on ‘Nina Simone: Four Women’

“Sydney Charles is an incredible talent… She projects an incredible vocal range and delivers every song with perfection. “

- PerformInk on ‘The Wiz’

“Charles almost stole the show with her portrayal of Tillie. She was amazingly funny with her spot on performance . “

- Chicago Now on ‘Guess Who’s Coming to Dinner’

photo by Joel Maisonet

bio

Sydney Charles has been in the room the whole time. You just didn't know her name yet.

A Chicago-born creative whose output refuses singular category, Charles left a successful career in banking and financial operations to commit fully to the art — and proceeded to build one of the most quietly formidable bodies of work in American theatre.

Her stage credits read like a tour of the city's most important stages: Safronia at the Lyric Opera of Chicago, multiple productions at Steppenwolf and Goodman Theatre, The Color Purple at Drury Lane, Nina Simone: Four Women at Northlight, Her Honor Jane Byrne at Lookingglass, Guess Who's Coming to Dinner at Court Theatre, Cullud Wattah at Victory Gardens — and that's the short list. A Black Theater Alliance Award winner, multiple Jeff Award nominee, and Chicago Reader "Best Stage Performer" runner-up, she is a 2025 NewCity Magazine Theatre Hall of Fame inductee and recipient of the 3Arts Make a Wave Award.

As a director, she has shepherded new work at Jackalope, Artemisia, and Wildclaw, served as Associate Director on Bug at Steppenwolf before its Broadway transfer, and most recently as Associate Director on the Tribeca-premiered, Webby Award-winning Hamlet for Make-Believe Association.

In audio, she co-created, wrote, and starred in Lake Song — a Webby-nominated, Signal Award-winning drama and Tribeca Audio Premieres selection. Her voice has moved product for McDonald's, M&Ms, and Xfinity. Television credits include The Chi, South Side, and Shameless, among others.

A three-time Write Club Chicago winner and grant review panelist for DCASE and the University of Chicago Arts & Public Life program, Charles is also the founder of Kaya Chronicles — a Chicago-based creative production company building narrative experiences at the intersection of sound, story, and community, rooted in the belief that storytelling heals.

A proud member of AEA, SAG-AFTRA, AGMA, and Delta Sigma Theta Sorority, Inc., she is represented by Stewart Talent and managed by ETC and Company.

Sydney Charles has always been here. Now you know.

“There’s nothing like performing. It is not about the attention for me; it’s about being fulfilled. “

photo by Matthew Gregory Hollis

Credits

Stage

Safronia - ‘Ensemble’

Lyric opera of chicago

Welcome to Matteson - ‘Patricia’

congo sqUAre theatre company

Last Night and the Night Before - ‘Rachel’

steppenwolf theatre company

The Most Spectacularly Lamentable Trial of Miz Martha Washington - ‘Priscilla’

steppenwolf theatre company

Cullud Wattah - ‘Ainee’

VICTORY GARDENS THEATER

Gem of the Ocean - ‘Black Mary’

Goodman Theatre

Her Honor Jane Byrne - ‘Marion Stamps’

Lookingglass theatre company

I Hate it Here - ‘Ashawna/Ms. Marcy/Tanya’

goodman theatre

Duchess! Duchess! Duchess! - ‘Duchess’

Steppenwolf Theatre company

I Hate It Here - ‘Ensemble’

STudio theatre

Wally World - ‘Ariadna’

steppenwolf theatre company

The Color Purple - ‘Shug Avery’

Drury lane theatre

Lottery Day - ‘Zora’

Goodman Theatre

Nina Simone: Four Women - ‘Nina Simone’

Northlight Theatre

Flyin’ West - ‘Fannie Dove’

American Blues Theatre

Father Comes Home From The Wars (Parts 1, 2,& 3) - ‘Second’

Goodman Theatre

Guess Who’s Coming to Dinner - ‘Matilda “Tillie” Binks’

Court Theatre

Insurrection: Holding History - ‘Mistress Mo’tel’/’Gertha’

Stage Left Theatre

A Swell in the Ground - ‘Olivia’

The Gift Theatre Company

An Octoroon - ‘Minnie’

Definition Theatre Company

Spamilton - ‘Renee’

Royal George

The Wiz - ‘Dorothy’

Kokandy Productions

The Snowy Day - ‘Mom’/Female Player

Emerald City Theatre

Octagon - ‘The Watcher Named Pen’

Jackalope Theatre

The Fly Honey Show - Company Member

The Inconvenience

Prowess - ‘Zora’

Jackalope Theatre

Myths and Hymns - ‘Woman 2’

BoHo Ensemble Theater

Ragtime - ‘Sarah’

Big Noise Theater

Dessa Rose - ‘Dessa Rose’

Bailiwick Chicago

Mr. Chickee’s Funny Money - ‘Lynetta’ (US)

Chicago Children’s Theater s

The Color Purple - ‘Darlene/Ensemble’

Mercury Theater

Smokey Joe’s Café - ‘Brenda’

Theo-Ubique Cabaret Theater

Cats - ‘Grizabella’

Theo-Ubique Cabaret Theater

Readings/Workshops

The Devil Wears Prada - ‘Ms. Mills/Ensemble’

Broadway nyc

Greetings From Moscow - ‘Masha Chekova’

Timeline Theatre Company

Jackson State Kent State - ‘Myrtle Green’

Timeline Theatre Company

Purlie Victorious - ‘Lutiebelle’

Broadway NYC

Wade - ‘Frankie’

Goodman Theatre

Florissant and Canfield - ‘Rubix’

Goodman Theatre

Girls in Cars Underwater. - ‘Bree’

Victory Gardens

Film/TV

The Chi - ‘Maisha’s Mom’

Showtime - nancy mejia

South Side - ‘Mrs. Fontineaux’

hbomax/Comedy Central - michael blieden

The Chi - ‘Retha’ (Maisha’s Mom)

SHOWTIME / SAM BAILEY

The Right Swipe - ‘Chynna’

OpenTV/ Independent / Justin Casselle

The T - ‘Becca’

OpenTV/ Independent / Bea Cordelia Sullivan-Knoff

Shameless - ‘Grace ‘

Showtime / Emmy Rossum

Did It Before - ‘Sydney’

Independent / Mamadou Sewa Bah

The Haven - ‘Fae’

Independent / Layne Marie Williams

Empire - Featured Vocalist

FOX / Debbie Allen

Commercials

Academy Sports & Outdoors - ‘Mom’

One at Optimus / Tim Mason

WBEZ Radio

Mercury Theatre - Radio Commercial

Clear Channel Communications

Director

The Last Senior Home in Bronzeville - Director

workshop productions with DCASe and Goodman theatre & definition theatre

Ghost Trap - Director

Artemsia theatre

Hamlet - Associate Director

make-believe association

The Gizzard of Brownsville - Director

artemsia theatre

A Drop In The Bucket - Director

Jackalope theatre

Ma(s)king Her: FutureWomen - Director

OTV/honeypot performance

The Whisperer’s Apprentice - Director

sideshow theatre

Bug - Dramaturg/Assistant Director

Steppenwolf theatre Company

His Shadow - Associate Director

16th Street Theatre

The Shipment - Associate Director

Red Tape Theare

Loaners - Director

Wildclaw Theatre

The Wiz - Assistant Director

Chicago State University

Awards

3Arts Make a Wave Award Recipient

3Arts

2022 Players 50 Theater/Music/Dance/Comedy

Newcity stage

2020 Players 50 Theater/Music/Dance/Comedy

Newcity stage

Best Supporting Performer - Guess Who’s Coming to Dinner

Joseph Jefferson Award Nomination

2018 Players 50 Theater/Music/Dance/Comedy

NewCity Stage

Leading Performance in a Musical – The Wiz

Time Out Chicago Theater Award Recipient

Best Actress in a Musical – The Wiz

Black Theatre Alliance Award

Best Actor in a Musical – The Wiz

The Hawk Chicago Award Recipient

Best Actress in a Musical – The Wiz