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How Dave Chappelle Helped Me Understand The World Better

From its social commentary to its musical guests, watching Chappelle’s Show defined my friendships and my outlook on life.

July 27, 2016

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For me, there’s one true test a pal must pass to make sure they’re a confirmed pal, to make sure that they get me and get it. Timeless and time-honored, that test begins when we sit next to each other and I, the test administrator, push play on my favorite Chappelle’s Show sketches. And I sit there, fully embodying the eyeballs emoji while waiting for this other human’s reaction as the show starts up. Then comes the big moment: either we laugh and crack up at the same scenes, hereby confirming the palship, or I begin mentally walking through how I’m gonna politely ask this person to leave as soon as the sketch is over.

This friendship foundation, the aforementioned “it” that Chappelle’s Show can represent, is the mutual understanding that the world isn’t perfect and peachy, but that there is a fantastically magical, freaking hilarious, and thought-provoking way of processing that reality. And that, for me and for many of the people closest to me, is often expressed through being a fan of Dave Chappelle and of Chappelle’s Show.


July 23, earlier this week, marked the 10th anniversary of its going off the air, after a brief third season. And, on this occasion, I can definitely say I wouldn’t be me if it weren’t for Chappelle’s Show. Perhaps most importantly, its existence created this weird and awesome safe space where I could understand and laugh at the flaws in the world with my friends. A mention of a specific sketch — like, just the word “Dylan” in reference to Season 2’s “Making the Band Sketch” — met with a laugh or high-five has brought the best people into my life and kept them there, from the middle school hallways of my youth to the office corridors of my adulthood.

“It’s been 10 years since the show’s been off the air, but its two-and-a-half-ish seasons were some of the most perfect and important television we’ll ever see.”

The show means a lot to me. Revisiting sketches over the years gave me more confidence to question and challenge the sus shit that might happen to me or my friends and family. For instance, after watching the protagonist in an instalment of the recurring “When Keeping It Real Goes Wrong” series stand up for himself, at the expense of his job, against a racist supervisor, I learned to do the same. Chappelle’s Show has also served as a constant, and necessary, reminder that time is passing, life is happening, but the system within which we function isn’t really changing at all. The “Celebrity Trial Jury Selection” sketch from the second season, for example, contextualizes the longstanding biases of law enforcement and the justice system, with celebrities as the punchline. More than once, as I’ve gotten older, a sketch has started with me laughing, then feeling shook, and then lost in thought.

And, lest we forget, the musical performances were other-worldly. Loving the artists who came on the show was almost an equally important aspect of “the palship test.” No other TV shows were doing it like this! Who else could have pulled off having John Mayer and Questlove perform together in a barbershop? Or getting Mos Def to deliver a legendary freestyle from the passenger seat of a car? No one. Throughout the many of the show's musical appearances, Chappelle was never too cool to freely geek to his favorite artists’ performances, even when those artists were standing right in front of him.

And it's highkey tight to know I don’t have to go too far to see Chappelle’s Show’s influence on some of the shows I've loved since, from Odd Future’s Loiter Squad to Aaron McGruder's The Boondocks and Black Jesus. Chappelle's Show’s influence — and his own, too — is present almost everywhere my interests in music, TV, and beyond lie. It’s been 10 years since the show’s been off the air, but its two-and-a-half-ish seasons were some of the most perfect and important television we’ll ever see.

Comedy Central
How Dave Chappelle Helped Me Understand The World Better