Dave Chappelle is Back

I think “What would it take for you to leave $50 mil?” would be a better headline, but…

Through my far too long and unmanaged Twitter feed, I discovered through New York Times that comedian Dave Chappelle is touring again.

Chappelle famously went into hiding after two seasons of his very popular Chappelle Show in 2005, despite being offered ginormous amounts of money (reportedly €50 million) to continue by HBO.

The fans applauded his bravado to get away from the “money machine” or whatever his intention was, but they were obviously at the same time sad and mystified. How long would he be gone for? Would he never come back?

But SEVEN (or so) years later he did.  This is what he said on Letterman: “Technically I never quit. I’m seven years late to work.” Letterman who’s witty and fast-minded himself had a good reply:  “Boy, are you gonna be in trouble when you go back.”

When you listen to the interview he seems a bit bitter that he left the scene for so long and missed out on all that money. He doesn’t seem to want to open up about why he left, maybe he’s tired of talking about it, maybe he regrets the decision not to take those $50 million. What he does talk about is how he and the guys at HBO couldn’t get along. And that’s what happens when you’re in the big money – creative freedom is gone and maybe that’s why Dave Chappelle got going?

The most interesting part of the Dave Chappelle interview with Letterman is from around 10:00 where he talks about money being the “fuel of choice” and the difference of $10 million and $50 million not being a huge lifestyle change, despite an “astounding” difference of $40 million.

If you’re interested in Dave Chappelle, I suggest this indie documentary. It’s great quality for an indie film production and definitely worth viewing.

Link: Chappelle’s Show -The 50 Million Dollar Question.

See bits of Dave Chappelle’s finest stand-up below. There’s plenty more on Youtube of course, but for someone who spent a good amount of time in D.C. this really hits home.

What would it take for you to leave $50 million?

Published by


Jonas: Writer. Talker. Thinker. Wine drinker. Brand builder. Tennis player. Family guy.

Leave a Reply

Your email address will not be published. Required fields are marked *