Dave Chappelle is back on top - would he really walk away again?

Comedian Dave Chappelle visits the District of Columbia’s Duke Ellington School of the Arts, which he once attended, during a visit last month. He was in Washington for shows at the Warner Theatre, where he was filming material for his third Netflix special.  CREDIT: Washington Post photo by Jahi Chikwendiu
Comedian Dave Chappelle visits the District of Columbia’s Duke Ellington School of the Arts, which he once attended, during a visit last month. He was in Washington for shows at the Warner Theatre, where he was filming material for his third Netflix special. CREDIT: Washington Post photo by Jahi Chikwendiu

WASHINGTON — Dave Chappelle went back to where it all began.

As a teenager, Chappelle worked stages in the D.C. comedy scene. He recorded “Killin’ Them Softly” at the storied Lincoln Theatre, telling jokes in the same space where Duke Ellington and Billie Holiday performed. The 2000 HBO special, considered one of Chappelle’s most quotable works, showcased the incisive, clever and downright ridiculous outlook on race and relationships that’d be on full display three years later during his breakout “Chappelle’s Show.”

Then, at the height of his career, Chappelle famously walked away: from a $50 million Comedy Central deal, from TV specials, from it all. And while he has performed stand-up in the intervening years - popping up in comedy clubs, closing out festivals - Chappelle is now having his most public moment in a decade.

He returned to Washington last month for a nearly two-week stint at the Warner Theatre, where he filmed material for his third Netflix special. His $60 million deal with the company also yielded two other stand-up hours, filmed in 2015 and 2016 and released in March, that became Netflix’s most-viewed comedy specials ever. Chappelle has since completed a star-studded, two-week Radio City Music Hall residency over the summer and quickly sells out shows.

But when he opened a recent Warner performance, Chappelle joked about how he’s ready to walk away again. You know, after he drops this next special.

He said part of it had to do with how “brittle” some ears have become. While that served as a premise for a bunch of jokes - honestly, you’ll just have to watch and see for yourself whether they work for you - it’s also a sentiment Chappelle has expressed before.

As stand-up comedy booms and the number of comedy fans has multiplied, “now there’s a big debate about how far we should be able to go, and you’ll see guys saying things that will really upset people,” Chappelle said in a brief interview with The Washington Post over the summer. “Getting on a big stage, it’s harder to really - not everybody’s ears are calibrated for this. But the people who like it, love it.”

The comic has some recent experience to draw from. Jokes in his first Netflix specials, particularly about transgender people, received some criticism. While filming for this next special, he doubled down on even more transgender material and incorporated the very criticism he has received.

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Stand-up gives Chappelle something his sketch comedy show didn’t: total artistic control. He’s 100 percent responsible for what he says on stage. He’s just saying it in a very different world.

Since he released his last special, 2004’s “For What It’s Worth,” public attitudes on key social issues have dramatically shifted. A majority of Americans then opposed same-sex marriage; now, a majority supports it. Calls for increased representation of people of color in movies and on TV have never been louder. There are more open conversations about sexual assault, and repercussions for celebrities accused of such misconduct.

Technology has also dramatically changed. In 2004, most audience members didn’t carry phones that could let them covertly film and publish sets for the world to see; YouTube didn’t even launch until 2005. There was no widespread social media, and rarely did the Internet drive mainstream news coverage.

Recent years have seen bits, picked out of the context of a live show, take on a life of their own, such as a 2014 Hannibal Buress joke about allegations against Bill Cosby. Chappelle requires audiences at his performancesto lock up their phones in magnetic pouches, but someone can still tweet or write about it after the fact. And sometimes jokes get written about as if they’re straightforward statements of opinion; a 2016 Observer story on a Chappelle drop-in set, where he riffed about Hillary Clinton and Donald Trump, caused quite the stir. Chappelle addresses that in his new act, too.

All of this has created an environment of increased awareness and accountability for stand-up comedians. Some longtimers, such as Jerry Seinfeld, have bemoaned how political correctness hurts comedy. But there have always been people who’ve found comics’ jokes distasteful, offensive or based on inaccurate premises. It’s just that now everyone is equipped with a platform to air their grievances, and more people are paying attention than ever. For better and worse.

Chappelle has long walked the lines between outlandish, offensive and sharp-witted. His latest material has him jumping from talking about being a father, to President Trump’s election, to finding humor in the darkest chapters of American history.

Not everyone will like what he has to say. And he won’t have “it” for everyone. But he’s still an expert of the craft who will always command a legion of fans eager to hear what he does.

So, sure, Chappelle could walk away again if he wants. And there’ll be an audience waiting, again, for his return.

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