CynCity Productions Wraps Filming on Landmark Chicago-Set Series "Messy Lola," Announces Early 2026 Premiere
CynCity Productions, a Chicago-based production company, founded by Actress and Executive Producer, Cynthia Kaye McWilliams, announced the completion of principal photography for its new independent comedy-drama series, “Messy Lola.” The 10-episode season, Created & Written by Kevin Douglas, is slated for release early 2026, with a promotional trailer set to air January 18, 2026 at the CynCity Productions launch party that will be held at Cine City Studios (2429 W 14th St).
Shot on location in Chicago, “Messy Lola” follows the titular Lola; a reluctant mother, flighty romantic partner, perpetually annoyed by her insufferable coworkers -who is an expert at managing the mess- just not her own.
The series, helmed by Executive Director, Blake Martin, is a vibrant embodiment of the CynCity mission: ownership, profit sharing, and an unwavering commitment to story. In alignment with that mission, Blake Martin and 1st AD, LaTaryion L.T. Perry led a “teaching set”, where industry veterans mentored emerging Chicago talent.
“We didn’t come to Chicago to shoot; we are Chicago, proclaims McWilliams. “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.”
The series is created and written by playwright and screenwriter Kevin Douglas, a
DePaul University graduate and an ensemble member at Looking glass Theatre
Company, who also serves as an Executive Producer.
“I created ‘Messy Lola’ as a love letter to the complex, funny, and resilient characters
that define this city,” said Douglas. “To see this vision come to life with a team that so
deeply believes in collaborative, artist-driven storytelling has been a dream.”
Blake Martin, following the success of his original series Sunday Evenings, served as
Executive Director, helming all 10 episodes. In a unique mentorship initiative, he guided
four emerging directors on set, one of whom was entrusted to direct several scenes
throughout the season.
Star-Studded and Chicago-Powered Cast:
The series is led by Cynthia Kaye McWilliams, who currently stars in Average Joe on
Netflix and has been a series regular on Coyote, The Last Days of Ptolemy Grey, and
The Real Husbands of Hollywood.
McWilliams is joined by a powerhouse ensemble including:
● Glenn Davis II, Tony Award-winning actor from Purpose, also seen in Billions and
King James.
● Anthony Fleming III, currently starring in Power Book IV: Force.
● Tracey Bonner (Sweet Magnolias, Raising Dion, Swagger).
● Jacqueline Williams, Mockingbird National Broadway Tour, 61st Street and Paper
Girls
● Heidi Johanningmeier (100 Days to Live, Chicago PD).
● Charles Andrew Gardner, President of Chicago SAG-AFTRA, Hamlet Podcast
Series, Heist 88, Somebody Somewhere
● Charence Higgins, a talented newcomer steeped in the Chicago stage
Through this project, a new model for distribution and ownership is being done. CynCity Productions is reimagining not only production but also distribution. The company will offer episodes for direct purchase on its own platform, alongside exclusive bonus content on the CynCity YouTube network. After the screening event in January, the trailer will also be visible on all CynCity Holdings’ socials and the CynCity Productions webiste www.cyncityproductions.studio which will be the main hub and viewing platform for future CynCity Produtions’ titles.
This direct-to-audience model ensures that consumer support flows directly to the artists and craftspeople who created the work.
“Ownership is our core principle—it’s the only path to true creative and economic
freedom,” McWilliams stated. “When you support ‘Messy Lola,’ you are not just buying
entertainment; you are consciously investing in a new ecosystem that values people
over conglomerates. You are directly supporting the writers, actors, cinematographers, and editors who bring this story to life.”
About CynCity Productions: CynCity Productions is a Chicago-based production
company founded by Cynthia Kaye McWilliams. Its mission is to reimagine the film and television industry by putting creatives at the center, focusing on ownership and profit-sharing. The company is an extension of McWilliams’ broader vision, which includes CynCity Creative—a multidisciplinary team of professional artists offering services to Chicago creatives—and CynCity Studios, a versatile creative hub located in the historic Bronzeville neighborhood on Chicago’s South Side. cynthia@cyncitycreative.com.
The production successfully wrapped on November 24, 2025, and has moved directly
into a streamlined post-production phase, on track for its 2026 release.