CynCity Productions Wraps Filming on Landmark Chicago-Set Series “Messy Lola,” Announces Early 2026 Premiere

CynCity Productions, a Chicago-based production company built on a model of creative ownership and equity, announced today the completion of principal photography for its new independent comedy-drama series, “Messy Lola.” The 10-episode season is slated for a phased release beginning February 9, 2026, with a promotional trailer set to air on January 18, 2026 at the 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 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.  It’s a “Teaching Set” and Investment in Chicago Talent.

The series is a vibrant embodiment of the CynCity mission, operating as a “teaching set” were industry veterans’ mentor emerging Chicago talent. This initiative was led by veterans like LaTaryion “LT” Perry (1st AD & Executive Producer), who oversaw the training of production assistants and 2nd ADs, ensuring every department balanced execution with education.

“We didn’t come to Chicago to shoot; we are Chicago. This city’s energy, talent, and stories are the heartbeat of Messy Lola”, said Cynthia Kaye McWilliams, Founder of CynCity Productions and star of the series. “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 Artistic Associate at Lookingglass 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, 61^st 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.”

Tickets for the January event will go on sale soon, so follow CynCity Studios to stay in the loop with all the latest updates.

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