CynCity Productions Announces World Premiere Trailer Event for Chicago-Set Series ‘Messy Lola’

06 Jan 2026

CynCity Productions, the Chicago-based production company rooted in creative ownership, equity, and artist development, proudly announces the completion of principal photography on its highly anticipated independent comedy-drama series, ‘Messy Lola’. The 10-episode season will roll out in 2026, beginning with a world premiere trailer debut and red-carpet celebration on Sunday, January 18, 2026.

The official trailer premiere event will take place at CineCity Studios (2429 W 14th St, Chicago, IL), inviting guests to walk the red carpet, meet the cast and creative team, and celebrate a series that boldly proves sometimes the mess is the main character. Tickets for the event are available now at CynCityCreative.com.

Starring Cynthia Kaye McWilliams, ‘Messy Lola’ centers on Lola, an expert at managing the mess, just not her own. Set against the vibrant backdrop of Chicago, the series explores adulthood in all its beautiful disorder, including work, reluctant motherhood, dating, and the possibility that a lot of us are walking around with undiagnosed mental health issues, as Lola attempts to maintain control over a life that is, by her own design, messy.

Shot entirely on location in Chicago, Messy Lola also serves as a groundbreaking “Teaching Set”—a living investment in local talent. CynCity Productions intentionally paired seasoned industry professionals with emerging Chicago creatives to provide hands-on mentorship across departments. Veteran First Assistant Director and Executive Producer LaTaryion “LT” Perry led the initiative, overseeing the training of production assistants and second ADs while maintaining a high-level professional production environment.

“We didn’t come to Chicago to shoot—we are Chicago,” said Cynthia Kaye McWilliams, Founder of CynCity Productions and star of the series. “This city’s talent, energy, and stories are the heartbeat of ‘Messy Lola’. Our goal was to empower artists both in front of and behind the camera. We’re not just making a show—we’re building a future.”

The series was created and written by acclaimed playwright and screenwriter Kevin Douglas, a DePaul University graduate and ensemble member at Lookingglass Theatre Company, who also serves as Executive Producer.

“I created ‘Messy Lola’ as a love letter to the complex, funny, resilient people that define this city,” Douglas shared. “Seeing this story come to life with a team that truly believes in artist-driven, collaborative storytelling has been incredibly meaningful.”

Executive Director Blake Martin, following the success of his original series ‘Sunday Evenings’, helmed all 10 episodes. In keeping with CynCity’s mentorship model, Martin guided four emerging directors on set, with one director entrusted to lead multiple scenes throughout the season.

A Chicago-Powered Cast
Led by Cynthia Kaye McWilliams (Average Joe – Netflix; Coyote; The Last Days of Ptolemy

Grey; The Real Husbands of Hollywood), the ensemble cast includes:

Glenn Davis II, Tony Award-winning actor (Purpose, Billions, King James)
Anthony Fleming III (Power Book IV: Force)
Tracey Bonner (Sweet Magnolias, Raising Dion, Swagger)
Jacqueline Williams (Mockingbird National Tour, 61st Street, Paper Girls, Moses the Black)
Heidi Johanningmeier (100 Days to Live, Chicago PD)
Charles Andrew Gardner, President of Chicago SAG-AFTRA (Heist 88, Somebody Somewhere)
Charence Higgins (Describe the Night. – Steppenwolf Theater Company, Twelfth NightChicago Shakespeare Theater)Reimagining Distribution & OwnershipCynCity Productions is redefining how independent television reaches audiences. Following the January trailer premiere, Messy Lola content will be distributed directly to viewers through CynCity’s proprietary platform, www.CynCityProductions.studio, where the series will be available for purchase and will serve as the central hub for current and future CynCity titles.This direct-to-audience approach ensures that support flows straight to the artists and craftspeople behind the work.“Ownership isn’t just a value—it’s the path to creative and economic freedom,” McWilliams added. “When audiences support Messy Lola, they’re investing in a system that prioritizes people over conglomerates.”About CynCity ProductionsCynCity Productions is a Chicago-based production company founded by Cynthia Kaye McWilliams. Its mission is to reimagine film and television by centering creatives through ownership, equity, and profit-sharing. The company is part of the broader CynCity ecosystem, which includes CynCity Creative—a multidisciplinary collective serving Chicago artists—and CynCity Studios, a dynamic creative hub located in historic Bronzeville.