I Get It, Dave Chappelle. It’s Hard to Be a Comedian in Your Mid-40s

Dave Chappelle in Sticks & Stones. Photo: Mathieu Bitton/Netflix

Dave’s back, y’all. Dave Chappelle — whom you may know as the Half Baked dude or the “Rick James” bitch or the creator of some of the best comedy on the planet — is back, and he’s still poking at anthills with his edgy … joke … stick? My point is, Chappelle has a new special, Sticks & Stones, and the reviews have been a resounding “meh.” In it, he trods familiar, edgy territory, but he’s more defiant about it this time. He’s proud of his trans jokes, dismissive of cancel culture, and defensive of celebrity status. Overall, he comes off as a very rich old man yelling at today’s kids to get off his expansive lawn.

Why does Chappelle seem so out of touch? Yes, he’s wealthy enough to not have to mix it up with the hoi polloi, though I’m sure he’s appreciative of the dollars we fling at him for live performances. He’s not even that old — he just turned 46 on August 24. His chest hair is probably only now starting to gray.

My friend recently mentioned on Twitter her surprise at Chappelle’s age. I tweeted back my theory that Chappelle is probably dealing with an unexpected aspect of middle age: the hardening of your worldview, for better or worse. This highly scientific theory is based on me — my favorite test subject. I’m no Chappelle, but I am a comedian in my late 40s, and lately I’ve been spending a lot of time muttering to myself, “Now, that’s a messed-up thought, girl.”

This is not a defense or endorsement of Chappelle. He’s going to say what he wants to say, and I’m a comic, so my metric is usually “But was it funny?” It’s just … man, the 40s are such a forgotten age, y’know? There’s a great deal of hoopla about making it to 40, and then once you’re there, it’s like you don’t exist. Nobody wants to answer your questions; they just keep telling you to “do your Googles.” Next thing you know, you’re at a gathering and you say something like, “If you’re not a gender, how will you know what to wear to your office job?” and everyone will think, Whoa, has this clueless old man been here the whole time?

A mid-life crisis isn’t just buying a ridiculous vehicle, pulling a muscle at the gym, or leaving your wife. (It also doesn’t only happen to men, Hollywood, but we ain’t got time for that.) It’s realizing that after 30 years of my being the Go-To Voice (and ten years of diminishing returns), the world has stopped listening. So when you speak confidently about, say, music or sports or dating based on the way it’s always been and a young person informs you of the way it is now, it can knock you back on your heels. A decision must be made: Am I in the mood to reflect and adjust, or am I going to dig in my heels because it’s what I’ve always known? 

This was especially a shock to me because I’ve always (perhaps foolishly) thought of myself on the leading edge of progress. I’m not closed-minded! I’m hip! Look at the pro-choice bumper stickers on my Honda Prelude! Look at my “STR8 BUT NOT NARROW” T-shirt! But suddenly you hit 44 and you’re told, “Actually, it’s LGBTQIA,” and without thinking, you find yourself rolling your eyes and muttering, “What’s with all the letters? What happened to just ‘gay’?” (Weirdly, the pushback tends to start with the change of verbiage — oh, how we cling to our labels!)

Perhaps that’s why it’s surprising to hear Chappelle today. We’re used to Dave deftly walking us through minefields, with heart and humor. The defensiveness makes him seem crotchety. And maybe he is. But I also understand where it’s coming from. I’m out here trying to be funny around a lot of young people, and sometimes I get annoyed by their newness, too. I turn those ornery moments into material.

Full disclosure: I honestly thought the office-clothing thing. Not for a joke — that was a real thought. Fuller disclosure: I am currently working on (or stuck on, depending on how full your half-empty glass is) a joke where I say some of these nutso thoughts as examples of my brain turning on me. I’m stuck because I’m trying to find that triad of laughter, connection, and compassion. I want you to crack up and nod your head and murmur, “Yes!” even if you’ve never been through what I’m describing. I am often mindful of how I perform in front of various generations, and although I rarely let that stop me from telling a joke, it does influence the framing of my material. I’m saying to Gen Z, “Hey, here is why your parents are making awkward jokes about your friends. The world’s moving too fast for them, and their elbow hurts for some reason.” I’m saying to elder millennials, “Yes, you’re setting the tone now, but inevitably you will be pushed aside, and you may not be ready for it.” And I’m saying to Gen Xers, “Hey, I know it gets drafty, but don’t close up your mind just yet. There’s more to learn. Stay fluid. The kids say I’m using that word correctly.”

Luckily, I’m going through my 40s transformation away from most of the public. But there will come a day where I’m going to get tired of being so careful, and I’m just going to say what I want to say, feelings be damned. And there will be people who’ll agree with me, and they’ll laugh loudly because they, too, are tired of being careful. And I’ll start releasing albums with titles like Well, That’s Not How It Used to Be or Why Y’all Keep Changing Shit? I look forward to that freedom, and I can only hope that my old, unfiltered self is truly as cool as my younger self worked feverishly to be.

Shalewa Sharpe is a Brooklyn-based comedian. She has appeared on HBO’s 2 Dope Queens and Comedy Central’s The New Negroes and recently released her second album, So, You Just Out Here? She can be found on Twitter, Instagram, and Venmo at @silkyjumbo.

I Get It, Chappelle. It’s Hard to Be a Comedian in Your 40s