Meet Sydney

photo by Joe Mazza

“…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 is an award-winning multi-disciplinary artist from Chicago, IL. After a successful career as a banker and operations coordinator, she committed to the performing arts, bringing a unique blend of passion and purpose to her work on stage, screen, and as a director.

Her selected theatre credits include Welcome to Matteson (Congo Square Theatre), Last Night and the Night Before, The Most Spectacularly Lamentable Trial of Miz Martha Washington (Steppenwolf Theatre), Cullud Wattah (Victory Gardens Theater), Gem of the Ocean, Lottery Day, Father Comes Home From the Wars (Goodman Theatre), Her Honor Jane Byrne (Lookingglass Theatre), I Hate It Here (Studio Theatre - DC), The Color Purple (Drury Lane Theatre), Nina Simone: Four Women (Northlight Theatre), Flyin' West (American Blues Theatre), Guess Who's Coming to Dinner (Court Theatre). She has also portrayed Dorothy in The Wiz (Kokandy Productions) and Zora in the world premiere of PROWESS (Jackalope Theatre).

Her film and television work includes roles on The Chi, South Side (HBOMax), Shameless (Showtime), and the web series The T and The Haven. Sydney's voice has been featured in commercials for brands such as McDonald's, Xfinity, and Walmart. She is a co-creator, actor, and writer of the audio drama Lake Song, which won a Signal Award for songwriting and writing and was an official selection of Tribeca Audio Premieres.

Sydney made her directorial debut at Wildclaw Theatre’s Deathscribe Festival of Horror Plays and later directed Ma(s)king Her: Futurewomen in collaboration with OTV and Honey Pot Performance, as well as directing for Jackalope Theatre's 15th Annual Living Newspaper Festival. She also served as Associate Director for the revival of Bug at Steppenwolf Theatre.

As the founder of Kaya Chronicles, Sydney is dedicated to educating and empowering her community through art, cannabis, and healing. Her platform blends these disciplines to uplift those impacted by the War on Drugs and aims to create inclusive spaces for creativity and advocacy.

A proud member of Actors’ Equity Association (AEA), SAG-AFTRA, and Delta Sigma Theta Sorority, Inc., Sydney is a relentless fighter for equity and justice in every realm of her life. She is the recipient of the 3Arts "Make a Wave" award, BTAA winner and two-time nominee, multiple Jeff Award nominations, and recognized as a Chicago Reader "Best Stage Performer" runner-up.

Sydney's artistic journey is marked by deep gratitude for the support of her community and representation from Stewart Talent.

“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

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

A Drop In The Bucket

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