Chicago Actress Cynthia Kaye McWilliams Creates Her Own Comedy-Drama Series 'Messy Lola

Chicago actress Cynthia Kaye McWilliams has launched her own comedy-drama series after years of working within Hollywood’s constraints, according to a recent interview about her latest project.

“Messy Lola,” a 10-episode series filmed entirely in Chicago, premiered last month and follows the title character as she navigates motherhood, dating and undiagnosed obsessive-compulsive disorder, according to McWilliams. Episodes are available for purchase at messylola.com for $2.99 each, with new episodes released every two weeks.

McWilliams, a DePaul University Theatre School graduate who currently stars in Netflix’s “Average Joe,” said creating her own show fulfilled a long-held ambition after building her career with roles in Kevin Hart’s “The Real Husbands of Hollywood” and Amazon’s “Bosch.”

“‘Messy Lola’ has literally been my dream come true,” McWilliams said. “Your whole life as an actor — because you’re front-facing, people think that you’re the star. But in the world of film and television, truthfully, you are at the bottom of the totem pole.”

The actress explained how the traditional entertainment industry structure limited her creative control. “There’s so much that goes on in a production to set it up before you ever get there as an actor. You’re the last piece — an important piece, but the last piece — so you have the least amount of say,” she said. “With this series, I can do things I’ve never been able to do on camera because someone else limited me.”

The show was created and written by playwright Kevin Douglas, also a DePaul University graduate and ensemble member at Lookingglass Theatre Company, according to the production details. The cast includes Tony Award-winning actor Glenn Davis II, Anthony Fleming III from “Power Book IV: Force,” and “Sweet Magnolias” star Tracey Bonner.

McWilliams said the series addresses universal themes around mental health without stigma. “‘Messy Lola’ is sort of about the fact that we all are walking around probably with a little bit of undiagnosed mental health issues,” she said. “When we don’t deal with things it gets messier in our heads. It gets louder, more uncontrollable.”

The series showcases Chicago’s diverse neighborhoods, from the South Side to Bronzeville, Hyde Park to Englewood, highlighting Black businesses and community spaces throughout the city, according to the production.

Blake Martin, the executive director of “Messy Lola” who helmed all 10 episodes, said McWilliams had clear goals for the project. “Her goal [with the series] was to really do something different,” Martin said. “She really didn’t love the Hollywood machine and what it does to talent and what it does to brands.”

Martin, who has 25 years of experience in entertainment and fashion and hails from University Park, guided four emerging directors during the production process. He praised the show’s writing quality and tonal balance.

“Everything you do in film and TV has to start with the script and story — and the writing on ‘Messy Lola’ is just magnificent,” Martin said. “It’s so funny, so much depth, so much brilliance. It blends this unique balance of a big, funny laugh-out-loud comedy, but it also has moments of seriousness and tackling issues.”

The production completed filming over 24 consecutive days, according to Martin. He noted that support from the city of Chicago proved instrumental in the project’s development.

McWilliams emphasized her intention to present complex, authentic characters. “I love when Black women get to actually have joy, but I didn’t want Lola to be perfect — I wanted her to be flawed,” she said.