Colette Gregory BLACK BEST FRIEND To Steppenwolf's Lookout Series In June

The award-winning multi-hyphenate artist Colette Gregory returns to her Chicago home with her acclaimed one-woman show, Black Best Friend, as part of Steppenwolf's LookOut series June 12-14, 2025. All performances will take place at 8:00 p.m. in Steppenwolf's intimate cabaret-style 1700 Theater located at 1700 N. Halsted St.

Following celebrated appearances at The Peoples Improv Theater's SOLOCOM Festival and the Pack Hollywood Festival, Black Best Friend lands in Chicago before heading to the Edinburgh Fringe Festival in August 2025.

Part solo sketch comedy, part TED Talk, Black Best Friend deconstructs pervasive Black media tropes-like the "Angry Black Woman" and "Uncle Tom"-that have shaped public perception for generations. In just 60 minutes, Gregory reclaims the narrative through music, characters, and storytelling.

"As a festival director, I see many shows, and this show feels like the start of her comedic activism and required viewing for any white person..." says Alexis Di Gregorio, Festival Director for Packfest. "I laughed, cried, and was deeply moved as Colette held up a giant mirror to my face and showed me how I, as a white woman, am complicit in objectifying black women. It broke my heart and also empowered me to have the hard conversations and start shouldering the weight of necessary and needed change."

In 2019, Gregory made a stir locally after being let go from her position as Director of the iO Comedy Network at iO Chicago-a decision that sparked a viral online campaign of support. Since then, she has focused on independent content creation, crafting a unique brand of "artivism," art infused with activism, through solo characters, original comedic songs, and stand-up performances on social media.

"I want this show to entertain AND educate," Gregory says. "And for that to happen, it has to be funny and relatable to everyone. If you've ever felt like a sidekick in someone else's story, Black Best Friend is for you. Bring your laughter, your heart, and most importantly, bring your Best Friend."

Second City Chicago Mainstage alum and founder of Stepping Stone Theater, Julia Morales, serves as Director of the project. Morales is a Black and Puerto Rican performer, writer, director, teacher, and producer originally from Houston, Texas. A graduate of the American Musical and Dramatic Academy (AMDA), Morales began her comedy career after receiving the 2008 NBC Diversity Scholarship and has since performed globally, including with Norwegian Cruise Lines and The Second City Touring Company. She is a two-time Second City Mainstage alum and the visionary behind the community program 10,000 Hours, which helps aspiring improvisers hone their craft without breaking the bank.

Following the engagement at Steppenwolf, Gregory will take Black Best Friend to the famed Edinburgh Fringe Festival in August. The Fringe is an Internationally celebrated festival of performing arts that takes place in Edinburgh, Scotland each summer. Black Best Friend will be one of more than 1,700 shows presented August 1-25, 2025. To learn more visit edfringe.com.