If you’re feeling particularly good about yourself and you wish, for whatever reason, to immediately feel much, much worse, a great way to make this happen is to rewatch your favorite comedies and stand-up specials—particularly ones you haven’t seen in over a decade—and gawk in horror at how anachronistic some of them happen to be. Perhaps my favorite example of this is Chris Rock’s Bring The Pain, which also happens to be my all-time favorite stand-up special. This, of course, is the ground-breaking act that instantly elevated Rock past “working and generally known” comedian status to “all-time great.” It won two Emmys (Outstanding Variety, Music or Comedy Special, and Outstanding Writing for a Variety or Music Program), boosted his then-stagnant career, and led to two more HBO specials (Bigger and Blacker and Never Scared) that in totality could be considered the best three stand-up stretch any comedian has ever had. (Let’s just collectively agree to forget that Kill The Messenger ever happened.)

Although Rock tackled myriad subjects in Pain—dissecting and deconstructing them with his signature confidence and repetitive cadence—it’s best known for his now-iconic “Niggas vs Black people” bit, where Rock separates the black community in two (“black people” = good and “niggas” = bad) and expresses a wish to “join the Ku Klux Klan” so he could “do a drive-by from here to Brooklyn.” If only we could find a way to get rid of those pesky niggas, we’d be fine.

After watching the bit again this morning, 21 years after it first aired, it's still funny. But only because of Rock’s wit, delivery, and timing, and the examples he uses for his juxtaposition. Now, though, whatever humor it possesses is swallowed by the reek of respectability politics; you watch and realize there really isn’t much difference between how Rock describes “niggas” and how racists regard niggers. While watching it in the ‘90s, I felt like I had to turn on my brain to fully appreciate his work. When watching it now, I have to turn it off.

"While watching Chris Rock's comedy in the ‘90s, I felt like I had to turn on my brain to fully appreciate his work. When watching it now, I have to turn it off."

Now, Chris Rock is still one of my favorite comedians. Perhaps my favorite. And I don’t intend to diminish his status by dissecting a two-decades-old special he created at 30 and spotlighting it as specifically outdated. Bring The Pain is just an example of how comedies tend to be snapshots of a moment of time—reflections of the politics and the cultural zeitgeist when they were created—not living and breathing artifacts that evolve and grow as we do. From The Honeymooners and I Love Lucy to The Jeffersons and Eddie Murphy’s Raw, many (if not most) comedies recognized as iconic just would not be able to air in primetime today. And it’s not because we’ve collectively lost our sense of humor. The rules of comedy—particularly, the rules on where it’s socially acceptable to mine humor from and how to articulate that humor—have changed. And the best comedians, at least the truly transcendent male icons like Louis C.K. and even Rock (whose recent interviews and work suggest that his sensibilities have shifted to reflect our times and his circumstances), don’t just evolve with us. Like the best artists, they help to spearhead the evolution.

And this is why Dave Chappelle’s recent Netflix specials are so disappointing.

Perhaps my expectations were too high. I hoped that Chappelle, now entering his mid-40s, would have used his signature slyness and world-weary insights to tackle subjects more daunting than the low-hanging and dated comedic fruit of trans people, rape, and famous black men (O.J. Simpson and Bill Cosby) accused of horrific crimes against (mostly) white women. Especially after taking a full decade away from the public microscope. And especially during a time when there seems to be so fucking much—politically, culturally, and racially—for a black comedian as sharp and shrewd as Chappelle to dive into. His focus on the horror of political correctness, instead, felt like something you’d expect to come from a megarich 43-year-old man from the outskirts of Ohio. Who, instead of evolving with the world, has remained stagnant and believes the world has gone mad while pining for time when things were simpler. Which is who he is.

I recognize the presumption and perhaps even self-indulgence of suggesting that I know what Chappelle should have been talking about better than he does. There are no emails and comments I hate worse than “Why did you write about this thing instead of this other thing I wanted you to write about?” and I’m doing this now. I do not wish to be that guy, especially when discussing Chappelle, a man whose break from the public came as a result of corporate forces trying to tell him what he could and couldn’t—and should and shouldn’t—talk about. He is a public figure whom we (black people) have collectively and justifiably circled the wagons for; sensitive to his wish for peace of mind, and his attempt to possess it; ultimately aiming to protect one of our icons from the scourge of capital letter Whiteness attempting to transmute him.

I just... I don’t know, I just would like for him to join us in 2017. There’s so much he can do here.

Damon Young is the editor-in-chief of VerySmartBrothas (VSB) and a professional Black person. He can be reached at @verysmartbros or damon@verysmartbrothas.com.

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