Stream It Or Skip It: ‘Deon Cole: Charleen’s Boy’ On Netflix, Trying To Be A Player At 50 When The Game Has Changed

This hour opens with footage of Deon Cole out at a restaurant with his mother, Charleen. While she asks him about what’s next for him and Netflix, he mostly just nods and smirks while giving side-eye to his camera phone. Will Deon’s new hour be an extension of his Cole Blooded Seminar, his mom wonders? No. Not at all. In fact, nothing will unfold the way she expects, Deon says at the end we should readjust our expectations. So…

DEON COLE: CHARLEEN’S BOY: STREAM IT OR SKIP IT?

The Gist: That special Cole’s mom referenced was the comedian’s debut hour for Comedy Central back in 2016. Since then, he has released a half-hour for Netflix in 2017, an hour for the streaming giant in 2019, and then another 40 minutes of material he’d been workshopping in 2020 which popped up on Netflix’s YouTube channel.
The guy you recognize from Black-ish and Grown-ish has a stand-up persona that’s closer to the guy you recognize from Old Spice commercials.

Cole now finds himself at a crossroads, and not just because he has turned 50. Although that milestone does prompt multiple routines about where he’s at in his life both personally and professionally, complete with lurid descriptions of sex in middle age, and what it means to be a gentleman these days.
What Comedy Specials Will It Remind You Of?: In the past, I’ve compared Cole as a cross between Mike Epps and Nikki Glaser…but I forgot to add former Saturday Night Live writer Jack Handey, because Cole’s signature mid-show bit in which he pulls out a joke book and a pen evokes his own version of Deep Thoughts.
Memorable Jokes: Cole has opinions aplenty on what women of any age should expect of men in terms of sex and relationships, at one point defending himself by suggesting: “Don’t be mad at me. This is God talking to you right now. I’m just a vessel.”
But he receives “testimonial hollers” when he mentions Tracy’s Dog sex toys. Don’t worry, if you’re not aware, he will make you aware “go ahead and put it in your phone…before you forget it” he tells the audience, acting out a woman trying to remember by repeating it as a mantra through gritted grinning teeth. Then he gets howls by humping the air (no stool needed for this guy), and more still when he delivers “the realist shit you’re gonna hear” when it comes to how and why men his age have sex with their partners. You’ll also find out how his preferences in women have changed over the years, and how he has adapted to maintain his player status.

And yet, at the same time, he also wants us to know he embraces his age now, and how it’s impacted his health and sex life alike.
As for Cole’s joke-book section, that 10-minute segment comes halfway through the special. Just as in past performances, he prefaces this all by framing these jokes as half-baked thoughts: “Hopefully they work, and if they do, cool. If they don’t, then I’ll never see y’all ever again.” Here’s one such thought: “You ever curse when you pray?”
And here’s something you don’t often see from a comedian with a Netflix special: Humility?! Cole acknowledges “I don’t think I’m where I need to be at in my career and shit. I think I’m almost there but I ain’t really there.” How he knows he’s not at Rock or Chappelle status, though? I’ll leave that to Cole to tell you himself!
Our Take: Cole manages a commanding presence, such that he induces multiple applause breaks, in several cases even just for introducing the premise. His audience can’t wait to see where he’s going to go with it next. And he’ll admonish them if they don’t seem to be onboard quickly enough. “Should be a few more of y’all clapping,” he tells the Brooklyn crowd after asking a certain demographic to make themselves known, adding: “You know I can see you, right?”
In his first Netflix hour, I noted that Cole seemed to fall in line with other Gen X men in comedy by complaining about what comedians can and cannot say onstage, despite the fact that they’re getting paid handsomely to lodge that very complaint. Clearly he has evolved on that point. Now, Cole commends the younger generations for standing up for their civil rights, acknowledging there are people in his generation who sadly still aren’t living their true lives — because homophobia ran so rampant. So Cole asks Gen Z for a compromise: “Be patient with us being patient with you, alright?”
Turns out there’s more reason for Cole to ask for patience, which he does in a tearjerking way after the crowd applauds his closing bit.
He slowly pulls back the curtain on how the show must go on, no matter what’s going on in the entertainer’s personal life offstage. Unlike a few years ago in his first specials, “we not complaining. It’s part of the job. But you never understand what the comic is going through.”
The pandemic years have been cruel to his family, leaving him virtually alone after his aunt, two uncles, and his mother all have died. He didn’t have a dad growing up, either. “That shit devastated me, and I’ve been f—ed up ever since.” He reveals this taping took place on the first anniversary of her death, and it’s why the special bears her name, so her memory can live on. Cole knows the pandemic has been tough on everyone. He knows, too, that anyone his age (50 and older) also probably shares his pain in losing parents and beloved elders. So he implores us to be kinder to one another. Which he already hinted at earlier in the hour. Because he knows what we all eventually know: Time is currency. Don’t waste it.

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Our Call: STREAM IT. Even though we’re the same age, I’m not Cole’s intended audience for much of the hour. And that’s OK. I’m more impressed with his willingness to evolve and show his vulnerabilities onstage than whether or not he’s still acting out sexual moves onstage at his/our age.

Sean L. McCarthy works the comedy beat for his own digital newspaper, The Comic’s Comic; before that, for actual newspapers. Based in NYC but will travel anywhere for the scoop: Ice cream or news. He also tweets @thecomicscomic and podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.