MESSY LOLA Officially Premieres — First Two Episodes Now Streaming from CynCity Productions

Dennis Nichols
3 hours ago
3 min read

Promotional poster for Messy Lola featuring Cynthia Kaye McWilliams leaning over a table with colorful highlighters lined up in front of her. The title “Messy Lola” appears prominently, with supporting cast members pictured below in office settings. Text reads “CynCity Productions Presents” and includes writing and production credits. — Starring & Executive Produced by **Cynthia Kaye McWilliams**, this bold Chicago comedy-drama dives into workplace drama, complicated friendships, unexpected turns, and the kind of “mess” we all pretend we don’t have.

CHICAGO, IL — 02/22/2026 — Messy Lola, the highly anticipated Chicago-based comedy-drama from CynCity Productions, has officially premiered, with its first two episodes now streaming exclusively at messylola.com.

Starring and executive produced by Cynthia Kaye McWilliams, Messy Lola introduces audiences to a sharp, complicated, and unapologetically human woman navigating career turbulence, relationship chaos, reluctant motherhood, and the everyday mental gymnastics of adulthood.

The series embraces the tension between “the order we crave and the chaos we create” — delivering humor, vulnerability, and cultural authenticity in equal measure.

Written by Kevin Douglas and produced entirely in Chicago, the 10-episode season will continue its bi-weekly rollout through Spring 2026.

A Bold Start: Episodes 1 & 2 Now Available

The series opens with two dynamic episodes that immediately set the tone:

Episode 1 — Pilot: A workplace scandal forces Lola into an uncomfortable decision that could cost her everything.

Episode 2 — If It’s Too Good to Be True: Lola impulsively leaves her job for a dream opportunity — only to find herself scrambling to recover from the fallout.

The early release establishes Messy Lola as both comedic and emotionally resonant, blending sharp dialogue with grounded storytelling.

Promotional image for Messy Lola featuring Cynthia Kaye McWilliams standing with a thoughtful expression, surrounded by yellow sticky notes listing everyday worries like paying bills, calling dad back, locking the door, and making appointments. The title “Messy Lola” appears at the top, describing it as a new independent comedy-drama by Kevin Douglas. — Welcome to the inner monologue of **MESSY LOLA**.. An independent comedy-drama written by Kevin Douglas and starring Cynthia Kaye McWilliams, *Messy Lola* captures the hilarious, relatable mental checklist of modern adulthood — where ambition meets anxiety and the sticky notes never end.

Creator-Owned. Woman-Led. Chicago-Made.

Messy Lola represents a growing movement toward creator ownership in television. Through CynCity Productions, Cynthia Kaye McWilliams maintains executive leadership and intellectual property control, while investing in mentorship opportunities for emerging Chicago talent.

“Ownership is our core principle,” McWilliams states. “When you support Messy Lola, you're supporting a sustainable model for artists.”

By distributing directly via its own platform, CynCity Productions ensures creative control and direct audience engagement — a model increasingly defining the future of independent series production.

About Messy Lola

Genre: Comedy-Drama

Episodes: 10 (bi-weekly release)

Now Streaming: messylola.com

Messy Lola follows a woman who excels at managing everyone else’s chaos — except her own. With wit, honesty, and heart, the series explores modern adulthood through a distinctly Chicago lens.

About CynCity Productions

Founded by Cynthia Kaye McWilliams, CynCity Productions is a Chicago-based independent production company committed to authentic storytelling, artist ownership, and community-based production practices.

Media & Interview Requests

For press inquiries, interviews, or partnership discussions:

CynCity Productions

Website: messylola.com

Instagram: @messylolashow

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