​The time I met Dave Chappelle

Dave Chappelle is in the midst of a career resurgence. The stand-up comedian, actor, writer, et al is coming off a three-and-a-half-week headlining run this month at Radio City Music Hall. Chappelle is an extraordinary entertainer and Comedy Central agrees, ranking him #1 on their list of the "100 Greatest Stand-Ups of All Time." 

Chappelle is perhaps best known for his sketch comedy program “Chappelle’s Show” on Comedy Central. The broadcast ran from 2003-2005 and parodied such topics as racial stereotypes, politics, and pop culture. TV Guide put “Chappelle’s Show” #31 on their list of "TV's Top 100 Shows,” and it placed #26 on Entertainment Weekly's
​"New TV Classics."

Dave Chappelle 

At the time, Chappelle’s abrupt departure from the program that bares his name was shocking. The comedian left before the premiere of the third season, thus walking away from a multimillion dollar contract. His exit has been the subject of many stories and much speculation, and the performer even discusses the matter in his act.

However, long before all of this I encountered Chappelle in Downtown Detroit. Here’s that story.

​It was April 2001, and I had a late dinner with a group of friends on a Friday night in Greektown. Following our meal, we walked past the Atheneum Hotel around 11 o’ clock. There, I spotted Chapelle, alone and smoking a cigarette. He wore jeans and a jean jacket, donned a bucket hat, and carried a backpack.
 
“Are you Dave Chappelle?” I asked.
“Yep! Sure am!” he answered enthusiastically.

I stopped to chat for a bit. I asked him what he was doing, and he told me he had just performed a stand-up show at the nearby State Theater (now The Fillmore Detroit). I told him I enjoyed his humor and he expressed sincere gratitude. He said something like, “Thank you! Thank you! Appreciate that!”

Meanwhile, my amigos remained off to the side. They had no idea who he was and neither did any other pedestrians. “This guy is a comedian!” I tried to explain. “He’s funny! He’s on TV and in movies!” This was two years before “Chappelle’s Show” debuted, so the world had yet to hear the phrase “I'm Rick James, b***h!“ At this point, he was perhaps best known for his appearances on “Late Night with Conan O’Brien,” and supporting roles in movies, including “The Nutty Professor,” “Con Air,” and “Robin Hood: Men in Tights.”

Chappell as Rick James and in "Robin Hood."

Also of note: Chappelle may have been “under the influence.” He was swaying and made little eye contact. His state was entirely plausible if you’ve seen “Chappelle’s Show” or his stand-up act – there’s a lot of drug references in both. He also co-wrote and co-starred in “Half Baked,” a film about a group of friends who are, yes, half baked. Do I still need to make my case? OK. This is an actual Chappelle quote: “Hey, hey, hey, hey. Smoke weed every day.”

Our encounter ended when Chappelle asked us – I'm not making this up – if we could take him to a party. I was open to the idea, and I asked the group if they knew of anything. They, however, found his request odd and suggested we leave. (I thought it was a nice gesture! He took us for good people and wanted to hang out!) So, we left him as we had found him, milling about and enjoying a smoke. 
 
I still wonder, more than 16 years later, what would have happened if we had taken him to a wingding. What stories might have come out of it? It remains a great unknown.