Dave Chapelle’s Tough Lesson in Being a Groundbreaker

In 2005, comedian Dave Chappelle famously abandoned a reported $50 million contract. Rumors swirled about his mental health as the star bounced for an extended vacation in South Africa. It would be years before Chappelle began appearing in public regularly again.

At the time Chappelle’s success had been so meteoric, and his talent so lauded it seemed unimaginable that any hard-working entertainer would throw away such a huge payday after a lifetime of laboring to reach the top. Over the years Chappelle has explained that he wasn’t crazy, he was just burned out. Struggles with cable executives over the “controversial” nature of his content didn’t really lend itself to the creative process. Wanting to protect his artistic integrity (and his sanity) Chappelle simply chose to leave rather than have everything he worked for chewed up and spit out by the Hollywood machine.

While promoting his new Netflix special recently, the stand-up comedian told CBS’ Gayle King that it’s hard to watch the success of Key&Peele on Comedy Central knowing that they’ve built all that on the back of his own network struggles with Chappelle’s Show so many years ago.

“I fought the network very hard so that those conventions could come to fruition. So, like the first episode I do, that black white supremacist sketch. And it’s like, ‘Well, that’s 10 minutes long. It should be five minutes long.’ Why should it be five minutes long? Like, these types of conventions. I fought very hard. So when I watch Key & Peele and I see they’re doing a format that I created, and at the end of the show, it says, ‘Created by Key & Peele,’ that hurts my feelings.”

I feel for Chappelle but in a way this is just the natural outcome of being the groundbreaker. When you’re ahead of your time, you’re robbed of the benefits of experience. You spend so much energy pushing the boundaries that burnout comes quickly. By that time the new borders have been set and someone else is free to move into the empty space you’ve created.

I’m certain Jordan Peele and Keegan-Michael Key consider themselves inspired by Chappelle, rather than simple copycats. Chappelle made what they do possible. It’s the natural evolution of the creative arts. It is easy to understand Chappelle’s frustration but it isn’t anyone’s fault. If anything it’s his own fault for being too talented.

How different would his career be if Chappelle’s Show had been released a mere ten years later? These days when an artist is hamstrung by rigid executives he/she can move to any number of other formats to publicize their work while maintaining creative control. YouTube, Netflix, Amazon and a variety of streaming channels have all capitalized on the traditional struggle between cable executives and their artists.

Perhaps we would have seen seven seasons of Chappelle’s show instead of only two.

It’s all speculation, but nevertheless Chappelle seems to have reemerged to take advantage of the advancements in entertainment technology. This format seems tailor-made for him and the special is already receiving rave reviews across social media.

Dave, don’t think about guys like Key and Peele too much. You’re an innovator. Instead of feeling like your path got hijacked, look back with pride that before you there was no path at all. It’s good to see you back on that path and enjoying yourself. We’re glad to have you back.

Kira Allen