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Deon Cole’s love of comedy, community, and his mother shine in new special

Photo Credit: Clifton Prescod / Netflix

Hour after hour, and year after year, Deon Cole has always wanted to deliver his comedy in a way that makes people think. But this time, he’s still hoping to do just that, with just a little extra something to boot.

Unleashing his latest hour Charleen’s Boy, which premiered on Netflix last week, Cole just wants viewers, first and foremost, to laugh and take away from it his hope that we can enjoy life, be human, have fun, and not take our time together for granted. As the Chicago-grown comedy vet brandishes his evergreen style of relatable musings on everyday happenings, just as he has done over the course of more than 20 years on the grind, he makes it look easy — but with the added weight of a few factors, he’s here to assure that isn’t exactly easy, but fulfilling nonetheless.

“This is something from the heart, and it took me over two years to write and put together,” Cole tells Vanyaland. “Everything I do is out of love, and I hope people recognize that and notice that we take our time with these things, and as simple as it might look and seem, it’s really not. It takes time to talk about something that no one is talking about in the way you would like to talk about it. I would love for people to just enjoy it.”

One such factor, and the inspiration for the special’s final form, is the memory of Cole’s mother, Charleen. 

Recorded on the first anniversary of her passing, Cole felt the weight of the night right away, but following in the spirit of his mother’s unwavering and resilient approach to tough situations, Cole pressed on and delivered an all-around banger of a set. He’s the first to admit that it wasn’t his initial idea to name the special what it became or steer the material in the direction it wound up traveling that night, but he’s glad it did.

The organic nature of how the night unfolded, even with the now-obvious cloud hanging over him, had Cole firing on all cylinders with a drive to connect deeper with his crowd. Every element of this special was about coming together, and while he takes no credit for how the vibe fell into place, instead insisting that it was his mother’s doing from afar, he’s proud of how palpable the energy and camaraderie was between him and his audience, even well after the final curtain closed.

“Until I mentioned to the crowd that night what that day meant to me, and how it was the reason we were all there, nobody even knew, even after I had been talking about loss, and that brought a lot of people together,” says Cole. “There were so many people afterwards who hit up my DMs to talk about losses they were going through and how people expect you to be normal after losing someone who was your rock and foundation. They’ll say they’re sorry, but they’ll expect you to be normal, but it’s not normal anymore when something like that happens. I really think that came through [that night] and people started sympathizing with each other, and I saw something going in that room that I hope transcends across the world once people see this special.”

It was a truly heavy, yet cathartic night for Cole, but if he’s being honest, he essentially blacked out from the sheer intensity of the moment. Wiping the tears from his eyes and pulling it all together just seconds before hitting the stage, Cole knew what he was up against, but didn’t want to use it as a crutch for the show.

So, what the night resulted in was a fully rocking night of comedy, community and ultimately, empathy toward one another’s feelings with loss amongst the crowd. Even more, Cole couldn’t help but feel the resilient and loving spirit of his mother in the room, and he hopes that same feeling radiates from the screen as this special continues its journey through the world.

“It was almost terrible shooting it, but it was invigorating because my mother lives through me, and I knew this would ensure that her name would reign forever and never be lost,” says Cole. “I figured that ‘Charleen’s Boy’ would be perfect because, while it is her name, after all is said and done, that’s also who I am.”