The first time I saw Dave Chappelle…

The first time I saw Dave Chappelle was in Boston Massachusetts, at Wentworth Institute of Technology, in a gymnasium. It was either 1999 or 2000 I believe, and I was around 23 years old. I went with my boyfriend at the time who was a student at Wentworth. The gymnasium was sold out. Seating was composed of folding chairs and that old gym stadium seating that folded back against the wall when they wanted to use the gym for other purposes. We had front row seats, which is the last time I ever had front row seats to see Dave Chappelle… but even then I am still not sure how we, a couple of black kids, got those seats in an audience that was 90% white. I still remember looking around that gym, at that almost completely white audience, and wondering how/why they even knew who Dave Chappelle was. I remember watching him on Def Comedy Jam so to see him draw an almost completely white audience was shocking at the time. I had never seen a black comedian with a white following. I don’t remember any white people even talking about Def Comedy Jam back then. But besides that, it’s a very fond memory because I remember laughing so hard I almost fell out of my chair, right in front of Mr. Chappelle. Dude was and is hilarious. There was no opening act, no dj, no phones, and no social media. Just Dave up there in front of us with a mic. And he killed it. I was already a fan of his since Def Comedy Jam but that experience solidified me as a real Chappelle fan. He had brought laughter to me at a time when I was living in a city that was majority white, while also attending a majority white university, a completely different experience for me, a native Washingtonian.

That’s because Dave Chappelle was DAMN funny to me, a black woman, in a “white space.” I think that was the first time ever in my life that I was in a “white space” and was ever allowed to laugh about my black experiences. In fact, one of the other things about that show back then was we were able to tell exactly where the few black people were sitting throughout the audience because as each joke landed black people lost their minds. It wasn’t that non-black people didn’t get the jokes, it’s just that the jokes were especially funny because he was talking about his experiences from a black perspective. Dave Chappelle has always been able to deliver the black experience in a way that brings our pain to the forefront all while being funny to everyone, not just “us.” It’s quite masterful. It has made me look at him as a genius really. It takes a lot of deep thought to be able to deliver so many painful experiences into comedy brilliance. But he does it, and does it well.

Fast forward to last night. I was one of the 12,000 people who got to see Dave Chappelle in Las Vegas at the Mandalay Bay. (I did not have front row seats…) Mind you I have seen Dave Chappelle a few other times over the past five years, but last night really was special to me. To see an artist grow so much is amazing. Of course, as an artist Dave Chappelle has evolved but at his core he still does that special thing where he weaves the real black experience, the black pain, into a story that is both hilarious and informative. I won’t tell you what he said because the other thing that Dave Chappelle has done is bring back the experience of just watching a show. The no cell phones rule is one of the best things that he has ever brought to fruition.

This is my 4th time seeing Dave Chappelle with the no cell phones rule, and honestly, it’s the best. Because just like my first time seeing him, I don’t have any photos or videos, but I have the memories of experiencing something very special, just like last night. And the best thing about it is that I can say, I was there.



~Kai

P.S. If you haven’t already, go buy my book “Date Like A Woman“!!

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