He picked the perfect time to make a comeback. Donald Trump's America is a place so frighteningly chaotic that sometimes the most rebellious thing you can do is laugh at it.
Chappelle's comedy is the kind of smart, incisive, dark humor that's most useful when the political tide is running against it. He came to prominence in the early 2000s, when George W. Bush was president and the country's racial justice agenda seemed to stop at the symbolically fruitless task of burying the "n-word." His hit comedy program, Comedy Central's Chappelle's Show, poked fun at the racial pageantry of the United States, giving viewers countless classic sketches: the black white supremacist, Clayton Bigsby; the Niggar family; and the "Racial Draft," to name just a few.
And then, infamously, he walked away from it all at the peak of his fame in 2006, frustrated with a country content to laugh away its problems instead of fixing them. He was furious with how he felt he'd been used by the entertainment industry, and while he's often struggled to articulate his exact reasons for leaving the show, he has spoken at length about the freedom he felt after.
"That kind of attention wouldn't have been conducive to raising a family," he told People in 2014.
In an interview this week with CBS This Morning's Gayle King, Chappelle said his decision to walk away from his success was "about more than money." He used an analogy of a baboon who's tricked by a hunter intro trapping itself to prove his point.
"In that analogy, I felt like the baboon," he told King.
Though Chappelle walked away abruptly, he was around long enough to set the tone for how we talked — and joked — about race for roughly the next decade. And it was an important decade: an era that gave us our first black president, Barack Obama, who carefully — and often frustratingly — tip-toed through the minefield of race relations in America.
The Obama years were filled with moments seemingly ripe for Chappelle's brand of humor. Think Beergate — the time when the president suggested an injustice had been done when black Harvard professor Henry Louis Gates Jr. was arrested for trying to break into his own home in 2009. Obama notoriously walked back even that lukewarm criticism after receiving backlash from whites, who accused him of unfairly admonishing the police.
But those absurdities seem to pale in comparison to what's happening now. President Donald Trump has appointed Ben Carson to head the Department of Housing and Urban Development based strictly on the fact that Carson grew up poor, black and in Detroit. Carson, in turn, has downplayed the horrors of American slavery as "immigration." You can't make this stuff up — but you can laugh to keep from crying. And thanks to Chappelle, now we can do just that.
However, allowing viewers to laugh their pain off is not all that Chappelle's humor does. Like any timeless comic, Chappelle offers up a mirror into which America can look and witness its own absurdities. It shows truth to power. In today's case, the "power" — i.e., the Trump's administration — has proven especially sensitive to criticism. When Melissa McCarthy brilliantly portrayed a petulant White House spokesman Sean Spicer, Trump — always aware and controlling of public perception — was reportedly rankled in a way that far outweighed the criticism he's gotten from Democrats so far. Chappelle's humor has similar bite.
Comedy is one of culture's fiercest and most effective tools in moments of political strife. It allows viewers to make sense of their realities. It brings levity in times of chaos and fear. And, most importantly and at its best, it shows us that the world we live in was made that way by people who make very concrete choices about power, about policy, about everyday interactions and who suffers from them.
Nobody does this better than Dave Chappelle.