Inspiring Social Connection in the Pandemic Era – Chester Gregory

Some of you might know Chester Gregory from his memorable portrayal of Jackie Wilson, in “The Jackie Wilson Story”. He also had starring roles in “Hairspray”, and “Sister Act”, rapidly becoming known as one of the most promising voices in entertainment. Nowadays, Chester’s still working as an actor, musician, Broadway artist, and coach. But he’s also reaching out.

How, you ask? Through his social media presence, of course. It’s no secret that over the past year and a half, everyone’s been going a little bit mental what with the whole pandemic disaster, and all. And Chester Gregory, also known as C.H.E.S.S. on the social media platforms, rapidly recognized this, early on in March of last year, and started using his social media accounts not for self-promotion, but for human connection.

I just started sharing things that are of genuine interest to me; everything from zodiacs to mental health, to wellness to speaking out against social injustices. For too long, I have used social media to express an idea of who I am; recently I have let that idea go and found that I have been connecting with people on a deeper level, which matters most to me.

At the beginning of the pandemic, Chester began putting out what he calls “March to Wellness”, which were humoristic videos that were meant to inspire and encourage those followers struggling with the global situation. It can be said that the response to these productions overwhelmed even the artist himself.

It was a daily mental health check in with my audience. There was an overwhelming response and I was encouraged to continue sharing more of my personality and point of view. (…) Engaging with a community of like-minded people has been gratifying and with over a million likes and views, the community is expanding.

Not only that, but Chester Gregory is also promoting change and acting as an active source of inspiration on the social scene. Aside from his presence in entertainment, he’s also launched his very own line of branded content, which also happens to be a Black-owned business, which, as his Instagram channel says, is here to “support others”. His videos have taken on a social aspect, as well, making Gregory a figure for the hotly debated social justice issues regarding the Black Lives Matter movement.

I’ve found ways to speak truth through short form episodic content and people have found it relatable and humorous.

But overall, Chester’s presence on social media isn’t about any one thing. It’s about connecting with fellow human beings, especially now, in an era when people are feeling more and more isolated and alone. Chester Gregory is now no longer a simple artist, but also a social media icon, with an impressive mastership of marketing and social presence.

Although Chester’s actively building his presence on all social media platforms, he’s understandably most drawn to visual channels, like TikTok and Instagram, which he feels add the most to his brand.

I love them all for different reasons but use Instagram and TikTok the most. I create custom content for each platform I use. I have found that to be the best method to connect with my community.

All in all, Chester Gregory is one of those artists who have learned to rebrand and morph into whatever the world needs them to be, in this crazy day and age, and that’s what’s going to cement his place in history, not only as an artist, but as an entrepreneur.