**NOTE: This piece first appeared on Ebony.com during Chappelle’s SNL appearance when our Founder & Editor was the brand’s Senior Social Media Manager.

While learning about Dick Gregory, I read his groundbreaking stance on The Jack Paar Show from Joe Morton: 

“In Dick’s case,” Morton said, ‘I will not do your show unless you allow me to sit on the couch and make a connection with the audience after I’ve done my routine.’”

There’s an opportunity and advantage that comedians have that most professions don’t: the ability to connect. No matter your style, you get the chance to use the universal language of laughter to move hearts.

Dave Chappelle was a comedian who understood that concept.

Though Chappelle had breakout moments in movies like Half Baked, The Nutty Professor – where he and Eddie Murphy circulated comedic jabs toward one another,  and the Russell Simmons’ created Def Comedy Jam, he had a small amount of visibility in New York City. It wasn’t until the launch of The Chappelle Show on Comedy Central that changed his trajectory and ultimately, the representation of us on television.

Before Atlanta and InsecureThe Chappelle Show was a cultural statement that said Black art and Black creativity do not have to be placed in a politically correct package. Not only can we be wide awake (aka woke), we can also be entertaining, and thought provoking. The “box” doesn’t exist because our voice matters, no matter what the conversation. For two seasons, the satirical show contained the below elements, which led to the ultimate expression of Blackness on TV in the early 2000s.

The Storytelling

Bold is a Black man making fun of the Klu Klux Klan on national television. The skit where Chappelle plays Clayton Bigsby,  a blind Black man who thinks he is a White supremacist leader, is one of the funniest things I’ve ever seen.  Controversial? Hell yeah. But it was Chappelle’s voice and his way of bringing stereotypes and harsh realities of a culture to the mainstream. The comedian created moments that were simultaneously hilarious and poignant of the issues at the time.  He told stories with humor and heart while never lowballing his perspective on culture, race, and being Black in America. The Racial Draft. Remaking Roots.  Every laugh could be turned into talking points of discussion and a nod to our culture.  Where else could a new generation learn about the greatness that is Prince and Rick James?

The Music

As a kid, one of the best parts about classic comedic brands like In Living Color and the Arsenio Hall Show, was getting to see the musical acts. I can’t remember exactly when Soul Train went off the air but for awhile there was a void of Black artists performing live on national TV. And then, here comes Dave and friends. Kanye West. Q-Tip. Talib KweliCommon. Hearing Mos Def freestyling in the car as Dave drove around the city was the cool predecessor of the pop culture moments that now go viral. Could you image FLOTUS in a carpool karaoke set-up with Dave Chappelle?! That idea alone would change the world.

The Statements

Hurricane Katrina. Bush. Incarceration rates. Drug policies. It didn’t matter the topic or the issue, Chappelle was going to let his voice be heard. It didn’t matter who was trying to trademark Black culture at the time, he would talk about corporate America in their face and ON their network. The beauty was that he refused to be contained. When he decided to abruptly leave the show, he didn’t fear being black balled in the industry. He held his ground in the same way that Richard Pryor, Redd Foxx, and Dick Gregory had before him.

“And eventually, Jack Paar relented,” Joe Morton continued. “Dick Gregory went on to respond to the show and in that one moment, broke the color line in terms of comedians on late-night television.”

What lines will Dave Chappelle cross tonight on Saturday Night Live?

We’re not sure but as we head into this #NotMyPresident aka The Trump Era,  we do know that we have A LOT on our minds. Whatever he pulls out of his hat tonight, we know that he’ll make us proud.