Cynthia Kaye McWilliams Wraps “Messy Lola” — A Love Letter to Chicago and Creative Ownership
- Dennis Nichols
- 4 days ago
- 3 min read
Go behind the scenes with actress and producer Cynthia Kaye McWilliams as she opens up about her new series Messy Lola, creative ownership through CynCity Productions, and the power of building your own lane in Hollywood and beyond.
Premiere Set for February 9, 2026
CHICAGO, IL – (on November 15, 2025) — Cynthia Kaye McWilliams (@cyncityforever) and her production company CynCity Productions wrapped filming on Messy Lola, a bold new 10-episode independent comedy-drama. Set and shot in Chicago, the series will premiere February 9, 2026, with the official trailer debuting January 18 at the Cine City Studios launch event.
Created by Kevin Douglas (Lookingglass Theatre, DePaul University), Messy Lola follows a woman juggling reluctant motherhood, creative ambition, mental health, and dating — all with that very specific brand of chaotic grace. It’s messy. It’s real. And it’s intentionally built to uplift the next generation of Chicago creatives.
“We didn’t come to Chicago to shoot; we are Chicago,” says McWilliams, who stars in and executive produces the series.“We’re not just making a show; we’re investing in the next generation of storytellers.”
A Teaching Set. A Distribution Disruptor.
Messy Lola was filmed entirely in Chicago with a hybrid model of mentorship and professional production. First AD LaTaryion “LT” Perry and Executive Director Blake Martin mentored emerging local crew across every department — from PAs to directors.
“Ownership is our core principle,” McWilliams states.“When you support Messy Lola, you're investing in a creative ecosystem that values people over conglomerates.”
Episodes will be distributed directly via cyncityproductions.studio, with exclusive content available through CynCity’s YouTube and social platforms. This direct-to-audience model ensures artist revenue and access remain the top priority.
A Cast of Powerhouse Chicago Talent
Led by McWilliams (Netflix’s Average Joe, Ptolemy Grey, Real Husbands of Hollywood), the ensemble includes:
Glenn Davis II (Billions, King James)
Anthony Fleming III (Power Book IV: Force)
Tracey Bonner (Swagger, Raising Dion)
Jacqueline Williams, Charles Andrew Gardner, Heidi Johanningmeier, and Charence Higgins
READ THE FULL INTERVIEW
Go behind the scenes with Cynthia Kaye McWilliams in our exclusive SAM Series interview. From library stacks to directing sets, she shares how she turned chaos into content — and built a company to do it again.
Start creating your own story with @cyncitycreative — because the world doesn’t need a copy. It needs you.
Media Contacts:
Christi Love, With an Eye PR – (312) 451-3796 – [email protected]
Leroy Burton, LSB Media – (708) 539-1434
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