CynCity Productions, the Chicago-based company built on a model of creative ownership and equity, has wrapped principal photography on its upcoming independent comedy-drama series, Messy Lola, set to premiere in 2026. The 10-episode season will roll out beginning February 9, with a promotional trailer debuting at the launch party on January 18 at Cine City Studios.
Leading the series is Cynthia Kaye McWilliams, who also founded CynCity Productions, starring as Lola, a woman navigating the chaos of adulthood—work, reluctant motherhood, dating, and undiagnosed OCD tendencies—while trying to maintain a facade of control over her messy life. She is joined by a strong Chicago-powered ensemble including Glenn Davis II, Anthony Fleming III, Tracey Bonner, Jacqueline Williams, Heidi Johanningmeier, Charles Andrew Gardner, and newcomer Charence Higgins.
Created and written by DePaul alum and Lookingglass Theatre ensemble member Kevin Douglas, Messy Lola serves as a love letter to Chicago’s resilient, funny, and complex characters. Douglas also executive produced the series alongside LaTaryion “LT” Perry, who led a mentorship initiative on set to train emerging production assistants and 2nd ADs. Executive Director Blake Martin helmed all 10 episodes while guiding four emerging directors, one of whom directed several scenes.
The series embraces CynCity Productions’ innovative approach to ownership and distribution. Episodes will be available for direct purchase on www.cyncityproductions.studio, with exclusive bonus content on their YouTube network, ensuring support flows directly to the artists and craftspeople behind the project. McWilliams explained, “Ownership is our core principle—it’s the only path to true creative and economic freedom. Supporting Messy Lola means investing in a new ecosystem that values people over conglomerates.”
Shot entirely in Chicago, Messy Lola reflects CynCity’s mission to empower both on-screen talent and behind-the-camera creatives, offering a “teaching set” model where mentorship and professional growth are central to the production. The company’s hub, CynCity Studios in Bronzeville, will serve as the main studio for future releases, reinforcing their commitment to building a sustainable, artist-driven entertainment ecosystem.
The series wrapped on November 24, 2025, and is now in post-production, gearing up for its 2026 release.