Local actress Cynthia Kaye McWilliams possesses a creative range that displays the multifaceted nature of Black women. Her latest project, a comedy-drama series titled “Messy Lola,” premiered last month and hones in on her layered identity.
The 10-episode series, filmed entirely in Chicago, follows Lola as she deals with motherhood, dating and undiagnosed obsessive-compulsive disorder. McWilliams, a DePaul University Theatre School alum, has done everything from flexing her comedic chops in Kevin Hart’s hit series “The Real Husbands of Hollywood” to portraying an earnest detective on Amazon’s “Bosch.” Episodes of the show can be purchased through messylola.com for $2.99 each; new episodes are released every two weeks.
Though she currently stars in Netflix’s “Average Joe,” McWilliams said helming her own show after spending years in Hollywood was something she always wanted to achieve.
“‘Messy Lola’ has literally been my dream come true. Your whole life as an actor — because you’re front-facing, people think that you’re the star,” she said. “But in the world of film and television, truthfully, you are at the bottom of the totem pole.”
The star elaborated on how confining the acting world can sometimes feel.
“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. With this series, I can do things I’ve never been able to do on camera because someone else limited me. 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.”
In front of the camera and behind the wheel
The show was created and written by playwright Kevin Douglas, a DePaul University graduate and ensemble member at Lookingglass Theatre Company. It features an impressive roster of talent including Tony Award-winning actor Glenn Davis II, Anthony Fleming III (“Power Book IV: Force”) and “Sweet Magnolias” star Tracey Bonner.
McWilliams didn’t divulge if the series is autobiographical but insisted that it contains overarching themes that everyone can relate to.
“‘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. It’s very important that we stop stigmatizing and learn how to address ourselves, address issues in our families and address issues in life.”
She also believes there is humor to be found in life’s hardships.
“We also need to learn how to laugh about it and understand that it really isn’t that serious actually — everybody is out here struggling,” she said. Still, “Messy Lola” celebrates the beauty and richness of Chicago.
From the South Side to Bronzeville, Hyde Park to Englewood, the city’s diverse neighborhoods, along with Black businesses and spaces, are showcased in the show.
According to Blake Martin, the executive director of “Messy Lola,” McWilliams had a strong vision about reclaiming her storytelling ability. “Her goal [with the series] was to really do something different,” he said. “She really didn’t love the Hollywood machine and what it does to talent and what it does to brands.”
Martin, who helmed all 10 episodes, guided four emerging directors on set. This, along with the show’s depth, made for a memorable experience.
“Everything you do in film and TV has to start with the script and story — and the writing on ‘Messy Lola’ is just magnificent. It’s so funny, so much depth, so much brilliance,” Martin said. “It blends this unique balance of a big, funny laugh-out-loud comedy, but it also has moments of seriousness and tackling issues. It was an amazing 24 days of filming nonstop every day.”
Martin, who has worked in entertainment and fashion for the past 25 years, hails from University Park. He said that support from the city of Chicago was instrumental in his career.
“Chicago really rallied behind me, supported me, pushed me in times where I doubted myself … doubted my abilities,” he said. “Chicago was like, ‘No, you are one of one and whatever we need to do to stand behind you, we will.’ But this city invested in me and I’m not leaving until I give it all back.”
McWilliams echoed this sentiment. “We have to start creating our own infrastructures and ecosystems, and that means that we have to partner together,” she said. “If we go into it thinking about partnership and experience and quality product first, and trust that the money will come, then it will.”