We recently connected with Chester Gregory and have shared our conversation below.

Chester, thanks for joining us, excited to have you contributing your stories and insights. What’s been the most meaningful project you’ve worked on?

The most meaningful project I’ve worked on is undoubtedly “The Jackie Wilson Story.” This role was my breakout moment in the industry and marked a significant milestone in my career, leading to my Broadway debut. Portraying Jackie Wilson was a full-circle moment for me, considering he was Michael Jackson’s biggest inspiration, and Jackson was a major influence on my own journey. Additionally, Jackie Wilson played a pivotal role in launching Berry Gordy’s career, another icon whom I’ve had the honor of portraying.

The journey began with numerous auditions and rejections, but I was determined to bring Jackie Wilson’s story to life. The role required deep emotional connection, dynamic performance, and a genuine portrayal of his character. Over the span of 20 years, I’ve performed his work on and off, which has allowed me to connect with the Wilson family and their incredible legacy. This ongoing connection has been profoundly meaningful, as it has allowed me to honor and keep alive the memory of a legendary performer who has influenced so many in the music industry.

“The Jackie Wilson Story” was not just a role but a profound experience that shaped my career, connected me with a legacy, and reinforced the importance of perseverance and dedication in my craft.

Chester, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m an actor, singer, and digital creator. My journey in the performing arts began at a young age, fueled by a passion for storytelling and music. I grew up in Gary, Indiana, where I was deeply inspired by the vibrant local arts scene and the legendary Michael Jackson, whom I’ve had the honor of meeting.

I provide a wide range of creative works, including theatrical performances, music productions, and digital content creation. I aim to inspire and enlighten, bringing joy and thought-provoking content to my audience. My work is characterized by a blend of powerful storytelling, dynamic performances, and a genuine connection with my fans.

What sets me apart is my versatility and authenticity. Whether I’m on stage, in front of a camera, or creating digital content, I strive to bring my true self to every project. I’m most proud of my ability to connect with people from diverse backgrounds and make a positive impact through my art. For potential clients, followers, and fans, I want you to know that my mission is to uplift, inspire, and entertain, always staying true to the craft and to you.

Let’s talk about resilience next – do you have a story you can share with us?

Certainly. A key aspect of my journey that illustrates my resilience is my ability to remain teachable and coachable, which has allowed me to reinvent myself many times over. I’ve evolved from an actor and singer to also becoming a director, educator, speaker, author, and digital creator.

I’ve faced numerous rejections and setbacks, but I maintained a mindset of continuous learning and growth. This resilience and openness to feedback helped me land the role of Jackie Wilson, which became my breakout moment.

As I progressed in my career, I embraced opportunities to expand my skill set and take on new roles. Directing allowed me to see the creative process from a different perspective, and educating aspiring artists gave me a chance to share my knowledge and experiences while learning from the fresh perspectives of my students.

My work as a speaker and author further allowed me to reach broader audiences, sharing my journey and insights to inspire others. Venturing into digital content creation opened up new avenues for engagement, enabling me to connect with a global audience through various online platforms.

Each reinvention required adaptability, a willingness to step out of my comfort zone, and an eagerness to learn new things. This mindset has not only kept my career dynamic but also reinforced my resilience. By staying teachable and coachable, I’ve been able to navigate the ever-changing landscape of the entertainment industry, continuously grow as a professional, and make a meaningful impact in various fields.

Are there any resources you wish you knew about earlier in your creative journey?

Definitely. One resource I wish I had known about earlier is the vast array of online learning platforms and digital tools available to artists. When I was coming up, YouTube didn’t exist. Now, as an educator, I offer courses, community support, and private coaching designed to help others hone their craft, learn new skills, and connect with other creatives. Understanding the power of social media and digital marketing earlier on would have been a game-changer. These tools can significantly amplify your reach and help build a dedicated audience.

Another valuable resource is networking opportunities within industry organizations and events. Engaging with communities such as the Actors’ Equity Association, attending workshops, and participating in industry conferences can provide invaluable connections and insights that can propel your career forward. If I had tapped into these resources earlier, I believe it would have streamlined my journey and opened doors more quickly.

Contact Info:

• Website: https://www.chestergregory.com
• Instagram: https://www.instagram.com/chestergregory
• Facebook: https://www.facebook.com/chestergregory
• Youtube: https://www.youtube.com/c/OFFICIALCHESS
• Other: TikTok – www.tiktok.com/@chestergregory
  Spotify – https://open.spotify.com/artist/2Bilj0SkDO40wCxtBhs7t8?si=oL03AXBZR5S8AefqOERNHQ