True to her Capricorn star sign, Cynthia Kaye McWilliams has always been ambitious, dedicated, and has laser-focused discipline when she sets her mind to a goal. Her burgeoning CynCity brand, including CynCity Creative, CynCity Productions, and Bronzeville’s CynCity Studios, is a testament to her vision and determination to help solidify her longtime home of Chicago as a legit player in this new era of the entertainment industry going forward.
After earning her Bachelor’s degree in Acting from DePaul University, McWilliams has enjoyed a successful career in television and film, starring in such titles as Average Joe, Bosch, The Chicago Code, Coyote, Hard Miles, The Last Days of Ptolemy Grey, Prison Break, and the wildly successful ensemble sitcom Real Husbands of Hollywood on BET.
Her next project, the upcoming comedy-drama series ‘Messy Lola‘, finds her not only starring in but also serving as an executive producer under her CynCity Productions alongside writer/creator Kevin Douglas and director Blake Martin. Shot on location in Chicago, Messy Lola follows the titular Lola as she navigates the chaos and general annoyance of being an adult: work, reluctant motherhood, dating, and her undiagnosed OCD tendencies, all while trying to maintain a facade of control over a life that is, by her own design, messy.
Entertainment value aside, the series is more than just a show for McWilliams. The series serves as the first in a slate of projects designed to create jobs, train Chicago talent, and give artists profit participation, an uncommon opportunity outside of industry standards. As Chicago continues to grow as an entertainment hub, McWilliams is proving that creatives don’t have to leave the Midwest to succeed; they can build the industry here.
“We didn’t just come to Chicago to shoot; we are Chicago. This city’s energy, talent, and stories are the heartbeat of Messy Lola”, McWilliams says. “Our set was built to empower artists in front of and behind the camera. We’re not just making a show; we’re investing in the next generation of Chicago’s storytellers.”
N’DIGO recently caught up with the impassioned actress and entrepreneur to learn more about her plans for the CynCity brand and the importance of building it here in Chicago.
N’DIGO: In your own words, who is Cynthia Kaye McWilliams?
Cynthia Kaye McWilliams: At my core, I am a storyteller. Whether I’m embodying a character on screen, building a narrative for a brand, or crafting a film from the ground up, it’s all about telling stories that resonate, connect us, and often center on voices we need to hear more from. I’m a midwest girl, through and through—work ethic balanced with warmth, and a no-nonsense spirit is my foundation. And I’m a builder. I don’t just want to be in the room; I want to help build the room, open the doors wider, and set a bigger table for the folks coming after me.
What are three words family and friends would use to describe you?
Driven. Loyal. Nurturing.
Did you always know you wanted to be an actor, or did you dream of another profession?
I always knew I wanted to be in the arts. But not necessarily an actor. I started as a young writer – submitted a play to a local radio competition and was selected by that local theater – Martin Chislom of the MC Players! They produced my play, and when an actress couldn’t go up one night, I stepped in for her – the aliveness I felt, that specific form of communication… it just rewired me. I had to answer the call.
Who is the first actor that you remember seeing that inspired you?
Whoopi Goldberg. Full stop. Seeing her one-woman show on Broadway changed me. Well, I saw it on a PBS special airing and then on a VHS tape, not on Broadway, but it made its way to me and made an impact. The sheer command, the depth, the uncompromising strength and vulnerability she brought… It showed me what was possible. She wasn’t just playing a part; she was embodying souls. It told me, as a young Black girl, that our stories were worthy of that caliber of artistry.
How did you end up getting your start in the business?
My start was a combination of divine timing, preparation, and a leap of faith. After college, I moved to Los Angeles with my degree, my headshots, and a lot of hope. I started booking small commercial roles, but not much, and almost became a professional waitress. *lol* But then, funny enough, my first break was in a feature film called The Lakehouse, and it brought me right back to Chicago. Then I was cast in a recurring role in Prison Break – also here in Chicago. After that, it was a classic journey: years of auditioning, of “no’s,” of side jobs, of persistence. And then a few yeses that changed my life. That journey taught me the business from the ground up, which is invaluable to me now as a founder.
Please tell us about your CynCity brand and its various branches.
Our film and television production arm is CynCity Productions, where we develop and produce original scripted and documentary series and films that are compelling, character-driven, and often shine a light on underrepresented narratives. We’re in the business of making the content we want to see.
Also, there is CynCity Creative, which is a team of multidisciplinary creative professionals who focus on the strategic and branding side. Think of it as storytelling for businesses and brands. We help brands, non-profits, and organizations—especially those rooted in community—find and amplify their authentic narrative through video, digital content, and experiential marketing. It’s about making sure their “why” is communicated as powerfully as their “what.”
And finally, CynCity Studios is the brick and mortar space here in Bronzeville where we make all that happen. It’s also a resource, a space that can be rented for photography, self-tapes, intimate events, meeting space, retreats, filming, interviews, casting, podcast recordings, and more!
Who is Messy Lola, and why is the entertainment world abuzz about her?
Messy Lola! The name alone, right? Messy Lola is our first SAGunion production out of CynCity Productions—a comedy-drama series set right here on the South Side of Chicago. Lola is an expert at managing the mess—just not her own. She’s a reluctant mother, a flighty romantic partner, and perpetually annoyed by her insufferable coworkers. Her carefully controlled chaos is upended by the arrival of Kayla, a beacon of millennial optimism, who represents everything Lola is not.
I think the buzz and anticipation we’re seeing is because it’s fresh. It’s witty. It’s authentically Chicago, and it features a complex Black female lead we rarely get to see. We’re building something special with her.
Why was it important to you to bring your companies home to Chicago and grow them from here?
Bringing it all home to Chicago was non-negotiable. LA taught me the mechanics of the industry, but Chicago taught me story. This city, its rhythm and heartbreak and resilience—it’s all in me. There is an immense, often untapped, reservoir of talent here of writers, directors, crew, technicians, and more. I wanted to build a sustainable ecosystem here, to create high-level career opportunities so people don’t have to leave to chase their dreams. Investing here is a legacy act.
Best advice you’ve been given about the entertainment business?
“Your network is your net worth,” and I don’t mean that transactionally. It means the quality of your relationships and your reputation for integrity and excellence is the truest currency you have. Protect it.
Best advice to up-and-coming creatives?
Build your own table. Learn every facet of your craft and the business around it. If you’re an actor, learn about producing. If you’re a writer, understand directing. That knowledge is power and freedom. And cultivate your community—collaborate, lift others, be someone people want to work with again. In case you don’t know what that means- BE KIND.
Favorite quote or affirmation?
I have a little series I do on Instagram called Coffee Connections with Cyn, and we actually have affirmation cards that go along with it, and one of my favorites is: “I am rooted in purpose, and my path unfolds with grace and power.” It grounds me and propels me.
What’s next for Cynthia Kaye McWilliams and the CynCity brand?
We are in full swing on post-production for Messy Lola and preparing for the premier party and launch of another exciting series, Sunday Evenings, written and directed by Blake Martin. We have several other original properties we are developing for the 2026 slate. The dream is to make CynCity a premier destination for elevated, impactful storytelling, both for Hollywood and for brands worldwide—all emanating from Chicago. I see soundstages here. I see incubator programs for South Side teens. I see us being a case study for how to build a creative empire that feeds the community it comes from. We’re just getting started. The blueprint is drawn, and we’re building!
For more information on Cynthia Kaye McWilliams, the CynCity brand, and the upcoming Messy Lola premiere party event, please visit www.cyncitycreative.com and www.cyncityproductions.studio and connect with her on Instagram at @CynCityCreative and @CynCity_Productions.
