Conversations with Dennis Williams

Today we’d like to introduce you to Dennis Williams.

Hi Dennis, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
Dennis Williams (DeWill) is a visionary screenwriter and playwright whose creative journey has been marked by groundbreaking productions that redefine storytelling in the entertainment industry. With a trailblazing start in 2009, he astounded audiences with “I Just Want 2 Sing,” produced by production company Legendary Studio Shows.

His productions transcend boundaries, from sold-out stage plays like “Forgiving BUT NOT Forgetting”, the first theatrical play in history to premiere at the iconic Howard Theatre to the emotionally resonant “Love & Therapy Gone Wrong,” exploring deep-seated generational trauma. Breaking new ground in 2018, Williams took on the challenge of creating a musical, “I’ve Cried the Blues,” a searing exploration of societal issues in 1940s Little Rock, Arkansas. Premiering to rave reviews at Live Nation’s Warner Theater, this production showcased not just his writing prowess but also starred music sensations KeKe Wyatt and Avery* Sunshine, cementing it as a national theatrical triumph.

Relocating to Los Angeles in 2021, Williams wasted no time in creating waves with “Sincerely, Love,” a captivating scripted drama series unraveling a complex love saga haunted by unresolved pasts. His talent shone brightly during the pilot presentation tour in 2023, captivating industry insiders and building an intense anticipation for his debut TV venture among networks nationwide. Williams is a masterful storyteller with a proven track record of crafting narratives that resonate deeply and captivate audiences across mediums.

In 2025, Williams brought new life to his acclaimed musical I’ve Cried the Blues, featuring guest star appearances by Peacock’s Traitor and Real Housewives Alumn Candiace Dillard Bassett and 4x Grammy Award Winning artist Darrel Walls of The Walls Group.

The production delivered a Broadway-caliber cultural experience to audiences on national stages, and is now going to the pre-Broadway Theatre, The Shubert in New Haven Ct on May 2nd, with both guest stars returning to their powerful roles.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The journey has been steady, though not without its challenges. As the first in his family to attend college, Dennis graduated from Howard University with a degree in Radio/TV/Film. Living in the Washington, DC area, his dream job felt out of reach, so he decided to create his own path.

Armed with a speaker in his trunk and a single microphone, Dennis traveled throughout DC, partnering with venues struggling to attract patrons. He launched an open mic night concept designed to solve two problems at once, providing emerging talent a platform to showcase their work while driving revenue to local businesses.

His first event drew just four attendees. Rather than give up, Williams went back to the drawing board, rethinking his approach with a sharper focus on marketing and strategy. The result was immediate. His second open mic attracted more than 100 people.

Without the financial means to scale, Williams spent two years reinvesting proceeds from these events. That commitment led to his first major concert, featuring Grammy-winning artist LeToya Luckett at the legendary Howard Theatre. From there, he went on to work with world-renowned artists including Tweet, Luenell, Keke Wyatt, Avery Sunshine, and more.

Williams’ expansion and dedication to storytelling took him from intimate black box stages to national platforms, where he now entertains thousands through authentic bodies of work rooted in powerful storytelling.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I’m a producer, creative strategist, and storyteller at heart. My work lives at the intersection of live entertainment, culture, and impact. I specialize in building experiences that move people emotionally while also working strategically behind the scenes to make sure those experiences are sustainable, scalable, and commercially successful.

I’m best known for creating platforms where stories that are often overlooked are centered and celebrated. Whether it’s an open mic night, a concert, or a full theatrical production, my goal is always the same: to create spaces where authenticity is the main attraction and audiences feel seen, connected, and transformed. I don’t just produce shows, I build ecosystems around them, from talent development and audience growth to marketing strategy and long-term vision.

What I’m most proud of is creating something out of nothing and doing it consistently. I didn’t come from loads of money, industry access, or a safety net. I built my career by paying attention to what was missing and designing solutions that served both artists and underserved communities. Watching something that started with a single microphone evolve into nationally recognized productions and packed theaters is something I never take lightly.

What sets me apart is my ability to think creatively and strategically at the same time. I understand storytelling from the heart before is touches the stage. I know how to connect deeply with audiences, while also driving results, building partnerships, and sustaining growth. At the core of everything I do is intention. I lead with purpose, I honor the culture, and I make work that lasts beyond the applause.

Can you talk to us about how you think about risk?
I don’t think of risk as something dramatic or impulsive. For me, risk is about choosing faith over comfort and action over fear. I’m very intentional about the risks I take. They’re usually rooted in preparation, instinct, and a clear understanding of what’s at stake.

One of the biggest risks I took was betting on myself when the traditional path didn’t seem available. Instead of waiting for permission or opportunity, I created my own. That meant investing my time, money, and energy into ideas without guarantees. My first open mic night had four people in the room. That moment could have easily been a signal to stop, but I saw it as data. I adjusted, refined the strategy, and tried again. The next event drew over 100 people, and that experience shaped how I think about risk to this day.

Another major risk was reinvesting everything I earned back into my work instead of playing it safe. I didn’t have outside funding or a financial cushion. Every decision mattered and yes, sometimes it wasn’t profitable, but the works itself was always quality. I understood that growth required patience and discipline. Over time, those calculated risks led to larger stages, national visibility, and the ability to work with artists I once only admired from afar.

I see myself as courageous and calculated. I take risks that align with my purpose, not my ego. I ask myself whether the risk moves the vision forward, whether I’m willing to do the work if it fails, and whether the lesson will be worth the cost. When the answer is yes, I move.

Risk, to me, isn’t about avoiding fear. It’s about respecting it enough to prepare and still choosing to move forward.

Contact Info:

• Website: https://www.LSSUniversal.com
• Instagram: https://instagram.com/denniscre8ts
• Facebook: https://www.facebook.com/lssuniversal
• Youtube: https://www.youtube.com/@lssuniversal
• Other: https://www.IveCriedtheBlues.com

Image Credits
Image Credit: Mike Ware