Let’s Not Make This Awkward: A Survey of Dave Chappelle and Bill Cosby

by Michelle Viray on September 26, 2013


I laid there comfortably. I was coming off of some great painkillers thanks to a little minor surgery and moving had become a bother. It was beautiful outside but I had settled into a 6-hour marathon of ‘The Cosby Show’. It was one of my favorite episodes where Claire Huxtable tries to lose weight to fit into a dress as Debbie Allen played her no-nonsense trainer. The episodes fluctuated between seasons: from Rudy young to Rudy pre-teen from Lisa Bonet’s short ‘do to her long, flowing, dread-full (see what I did there) locks. I even experienced a little ‘jump-the-shark’ Olivia. I was enthralled. The episodes were funny, heart-warming, and insightful. They were timeless.

And, there I laid. Two and a half hours deep into doing nothing.

Truth be told, I was procrastinating.

It wasn’t the kind of Girls’ Season Two procrastination. That only lasted two episodes.

This was months.

Embarrassingly enough to admit, it was May.  Back in May I told my lovely editor that I would be “more than happy” to write a review of Dave Chappelle performing at The Chapel. “I will even write you a review of Bill Cosby at Mountain Winery while I’m at it!”


I don’t know where I got that bright idea. I said it, at the time, feeling confident that I could easily write a summary on two, outstanding comics, two distinct personalities, and sadly for me: one half-written, mediocre summary of one show come June.

I took my notes from the May shows everywhere, vowing to make edits and additions on plane rides to and from. Something always got in the way. Right now, it was Phylicia Rashad and Debbie Allen fighting over a crouton. Inspiration didn’t quite strike and here I was, 3 months later, reading a review on Dave Chappelle’s Funny or Die Oddball Festival Tour hitting Connecticut in between commercial breaks. Apparently the Connecticut show didn’t go as planned. Mr. Chappelle was heckled and left the stage.

Now, I won’t tell you I’m surprised. I’m not. I bet he’s heckled all the time. And, I would also put money on that fact it’s annoying. Really annoying. How many times could you hear a very popular catchphrase screamed at you regardless of where you were and who you were with? Yelled at you everywhere. Everywhere. You. Went.

(And you know which phrase I’m talking about because you just said it out loud.)

I wouldn’t be cool with it and I’m guessing, fine reader, you wouldn’t be either. But, I get it. You might be saying: “Please. He made millions of dollars off his show! He’s a celebrity! He can take it!” Sure. Sure. I wouldn’t say that you’re necessarily wrong. But, it brings a few questions to mind and conjures up feelings from one of the very first times I saw Mr. Chappelle perform in San Francisco:

At what point does someone not getting the point ruin it for everyone? When ‘not getting it’ becomes the majority, doesn’t the intended message get lost?

What I mean is this. Last night I saw the screaming eagle of soul Charles Bradley and his Extraordinaires perform at Great American Music Hall. To the sold-out crowd, Mr. Bradley spoke of love- loving yourself for who you are, loving the people around you for who they are, and never giving up on your dreams. He spoke of his own dreams of music and how his brother, who inspired his performing had been tragically shot and killed. As Charles Bradley poured out his heart, tears running down his face and sweat dripping from his forehead, they showed up. Four, tall dudes, getting drunk, making jokes, shouting to their ‘bro-hams’ across the floor, all the while wrecking the heart-felt moment for those in a 5 foot-radius, in addition, to wrecking my view of the stage. Did they not understand? Was this performance a joke to them? They clearly didn’t get the message of love and respect.

I have seen Dave Chappelle perform several times in San Francisco and only once did I see the audience treat him like Team Schmedium from last night. As Mr. Chappelle talked about his life experience and asked for questions from the crowd, he was interrupted by numerous “Chappelle Show” catchphrases. Not cool, San Francisco. You’re better than that. This was back in 2011.

But back in 2007, Mr. Chappelle addressed the ever-present question on the minds of the Punchline audience: Why did you leave?

I was lucky enough to witness the interaction between Dave Chappelle and the audience that night. I will not be able to do his delivery justice but, in summary, what Dave Chappelle said is this: “It wasn’t worth it to me anymore. I felt like people didn’t get the joke I was making and were taking it at face value.”

During the show at the Punchline, Dave Chappelle talked about his father being a teacher and how, as a young boy, he couldn’t understand why his father would be an educator when there wasn’t much money in it. “Everyone has their price” is what his father replied. With much wit, Dave Chappelle explained that at some point making a lot of money off Comedy Central wasn’t worth it. “And so I walked away. That was my price.” The words came and hung in the air. It was then I realized that Dave Chappelle was more than Sir Smoke A Lot, Tom Hank’s bookstore advisor, one of the highest paid comedians on television in 2004, or even the comic people wait for hours to see in a small venue. Here was a man who had real character. Becoming successful had not been easy and walking away from one of the highest paying gigs in comedy history had brought soul-searching and meaning rather than gold toilets and an impulsive gambling problem. Dave Chappelle had chosen not to compromise who he was and it was then, he explained, how his father’s words had now started to make sense. “Now do you know what I mean,” he said to the Punchline crowd. “What I mean when I say everyone has a price?”

That Punchline audience was very cool and respectful and Mr. Chappelle was awesome. He had jokes about the Lego house he had built in Japan, the Karate Kid movies, the Cincinnati Bengals, and homelessness in San Francisco. He tackled it all and the crowd doubled-over with laughter. The crowd got it. They understood. They could see through the sarcasm and the jokes and decipher between the heart-felt stories of his dad’s advice and colorful stories meant to entertain. Mr. Chappelle weaved a story that made you wonder what was true and what was fiction. And as an audience we couldn’t get enough. After 3 ? hours, Dave Chappelle left the stage but we still wanted more. We want more! He’s a comic that can deliver one word and tackle a controversial topic like no other person I’ve seen. It’s his deadpan delivery and the feeling that he knows more than he’s saying and, if you’re lucky, he might let you in on the rest of the joke. Dave Chappelle can take sad moments and turn them into side-splitting laughter. But, you have to get it. And to get it, you have to be smart and self-aware.

Let’s fast forward to The Chapel in May 2013. Dave Chappelle had done a series of shows at three different venues during the week: Yoshi’s, The Chapel, and The Independent. I was able to buy some tickets for one of The Chapel shows and wondered what to expect.

As I waited in line with everyone else on Valencia that evening, I didn’t know what I was in for. Would it be awkward? Would it be funny? Would the crowd be cool?

“Irony!” Dave Chappelle yelled above the screaming, packed-in crowd. “It’s a night of irony! I’m a black comedian who comes out to a white DJ. Who plays all-black music. With two Muslims as the opening acts. (pause) In a chapel.”

There were plenty of jokes that night. And, the crowd moved with the momentum easily. His opening story centered around ‘hopelessness’. Never would I have thought that anyone could make the Oscar Pistorius situation funny. But Dave Chappelle did with ease and it was amazing.

The topics ranged from possible movie pitches to Hollywood big wigs, international travel, car rides with Mos Def while witnessing the craziest homeless people in San Francisco to the Occupy Movement. All serious topics and yet this is the man that can make you cry from laughing so hard. Writing it down now seems ridiculous – laughing at the story of an athlete who is accused of shooting his girlfriend? That just sounds wrong. But Dave Chappelle has that ability in his delivery to take the saddest of sad and the weirdest of weird into a completely different direction. He has that gift. To make you laugh until it truly hurts. And if you’re smart, it will make you think about the message he is trying to deliver that lies beneath the laughter.

I’m glad I went to the show that night. The Chapel has great acoustics and for those that were able to get seating, a comedy show translates well to this venue. I also recommend the two openers from that evening: Mo Amer and Azhar Usman. Mo Amer’s impressions and stories of growing up as a Muslim in Texas had the crowd screaming.

For me, nothing will hold the same mystic feeling of that Punchline show back in 2007. Seeing Dave Chappelle as more than a comic and listening to his advice got me thinking. What is my price? In the way I live? In the way I treat people in my life- my friends and people I pass on the street? What does that say about me? And have you ever thought about it? Price means more than a dollar amount and some change in your pocket. As dark as this sounds and yet I don’t mean this in the darkest sense at all, but all things have some type of cost and some reward. And, sometimes it’s good to weigh them against one another. Sometimes, it can be beneficial to re-examine how you live and how you treat people. Or, maybe that’s just me.

I’ve thought a lot about that evening at the Punchline. And I have hoped for the chance to tell Dave Chappelle that I appreciate all he had to share. I loved the laughs but, for me, his words and deeper meanings gave me another way to think about my life. I’ve always wanted to say let him know, he’s helped me through some tough times.

As a comic, Dave Chappelle has amazing timing and his sarcasm doesn’t border mean-spirited or vapid. His take on serious topics like the economy, communities, life, international politics, pop culture trivia, and homelessness give pause. Pause to evaluate what you might think, while making you laugh. His journey through stardom and celebrity and the weight of his life lessons can seem slightly heavy (dare I say sad) and, it seems as though, there is more to the joke, the story, or the possible reality.

He is a man who has experienced the highest of the highs and the lowest of the lows. Walking away from the limelight for Dave Chappelle was something significant. It doesn’t always feel good being a butt of the joke.  (And, I realize the irony of saying this in a comedy show review.) It feels awful when you don’t know you’re the butt of the joke. But if you’ve been there, you know it’s devastating when you realize you’ve become the butt of the joke you created. But I suppose that is all a part life and growing up.

Now, growing up I saw a lot of Bill Cosby. If he wasn’t pitching me Jell-O pudding pops or eating sub sandwiches with potato chips, he was teaching his TV kids, and by transitive properties me, life lessons. (As a side note, ladies: statement sweaters are in for fall so, go ahead and get your Cosby on.)

At the 2013 Bill Cosby performance at the Mountain Winery, there was little fan fare. Mr. Cosby came out in sweats and needed little to accompany him. The stage set-up was minimalistic, especially when you consider this is a man who has been doing comedy since the early 1960’s. (He even got his start at the Hungry I in San Francisco.) Bill Cosby is more than a comedian. He’s an actor, producer, writer, musician, and educator. Mr. Cosby is a legend and he’s known for being an activist and for openly sharing his thoughts and opinions, met with some controversy.

But if you brought your children, which some did, to the lovely May evening in Saratoga, there was nothing controversial about his performance. Mr. Cosby talked about his love for the Bay Area and sweetly reminisced about performing at the Circle Star Theater in San Carlos back in the ‘70’s. It was an evening of story-telling.

Mr. Cosby started with stories of growing up. He began the night with: “A lot of comics will say, ‘I grew up poor and I didn’t know it.’ That’s the difference. I grew up poor. And I KNEW it!” He recounted stories of dates as a young man, trying to impress girls with his beat-up car. He mentioned being discovered by the famous William Harrah, who not only had Mr. Cosby perform in Tahoe at the beginning of his career but also took to him so much that he gifted him a Ferrari. Not bad for the young man who once had a keep a generator running to keep his car going. The history of Bill Cosby runs deep. I wished he would have talked more about Sheldon Leonard, the producer and director of “I Spy”. But Sheldon and his wife were the center of a hilarious story and remained only a mention.

Mr. Cobsy’s stories moved to the differences between men and women. Which lead to a gentle teasing tof the ladies in attendance and then to a respectful joking about his wife. The three hours flew by and all his stories rated PG-13. Considering the sold-out crowd was in fits of laughter and fully engaged the whole time, this is extremely rare AND impressive.

My favorite segments of the Cosby set included the stories of spending time with his wife and relying on his best friend Ed to help him out of a jam. His timing was impeccable, his natural and melodic,  and the crowd became engaged in a full call and response for the last hour. If you’re looking for an honest, clean show with a sweet spirit, then I highly recommend seeing Bill Cosby. It’s a legendary show and will immediately transport you to your childhood as an adult. Pudding cups and Ray Charles track not included.

Now, I’m not sure what Bill Cosby thinks of Dave Chappelle. And I don’t forsee Mr. Cosby making a surprise guest appearance at Shoreline on Friday. But I do suggest seeing Dave Chappelle at the Oddball Fest should you have the chance. If not, I suggest seeing him the next time he surprises a small club locally.

If you’re lucky, you will learn a thing or two.

Thanks to my editor for being so forgiving. In the spirit and the words of Mike Wilbon: I will try and do better next time.

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