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Dave Chappelle’s Mark Twain Prize comes at comedic crossroads

D.C. native honored at Kennedy Center as he picks up political baggage

Dave Chappelle during the Mark Twain Prize ceremony at the Kennedy Center on Oct. 27. (Evelyn Hockstein/For The Washington Post via Getty Images)
Dave Chappelle during the Mark Twain Prize ceremony at the Kennedy Center on Oct. 27. (Evelyn Hockstein/For The Washington Post via Getty Images)

Washington, D.C., native Dave Chappelle was in town Sunday night at the Kennedy Center to receive comedy’s highest honor, the Mark Twain Prize for American Humor. The lifetime achievement comes as the outspoken social critic is earning praise and criticism from unlikely political quarters, a sign of how political taboos have shifted since Chappelle began his career.

The Twain Prize is a recognition of Chappelle’s comedic influence over a three-decade career, from his early days as a local teenage stand-up to a performer commanding $60 million deals from giant online streaming services.

The award earned the comedian a shoutout from his home district representative, Del. Eleanor Holmes Norton, who praised his steadfast support for the city and his alma mater.

“Dave has never forgotten D.C. as his home,” she said in a statement.

Chappelle, who attended the Duke Ellington School of the Arts, donated his 2017 Emmy Award to the school, “impressing on the students that fighting the odds is possible,” according to Norton. The comedian recently shot a video promoting D.C. statehood and has been honored with a mural on the wall of Ben’s Chili Bowl on U Street.

But Chappelle, 46, has also drawn criticism for some of his recent output.

Those on the left say he’s displayed insensitivity to LGBTQ people, particularly transgender people, in his latest Netflix comedy specials. At one point he refers to them as the “alphabet community.”

He’s also received scrutiny from some in the #MeToo movement who say he’s being dismissive of victims of sexual harassment after his defense of fellow comedian Louis CK, who’s been accused of sexual misconduct.

Many on the right applaud Chappelle for attacking what they say is an overburdening culture of “political correctness.”

For instance, Donald Trump Jr. shared a clip from 2019’s “Sticks and Stones” in which Chappelle mocks actor Jussie Smollett, who said he was attacked in Chicago by Trump supporters shouting racial epithets. (An investigation by Chicago police cast doubt on Smollett’s account, filing charges that he filed a false report. Those charges were later dropped.)

Chappelle is a master storyteller with keen powers of observation. Much of his comedy articulates his sharp insights about race in America, using absurdity to flip ideas on their head. There is perhaps no better showcase for this than “Chappelle’s Show,” the hit Comedy Central sketch show he launched in 2003.

Whether it was a bit about a black white supremacist, a “racial draft” or imagining what George W. Bush’s presidency would be like if he were black, they all used absurdity to make his point.

While many of his views could be classified as politically liberal, Chappelle insists he’s not “a partisan dude,” telling CNN before the 2018 midterms that “if [someone I admired] ran as a Republican, I’d vote Republican.”

Chappelle’s was one of the first voices the country heard from after the 2016 election, when he hosted the Nov. 12 episode of “Saturday Night Live.” He used his 11-minute monologue to break down topics, including the election, police violence and Barack Obama’s presidency.

At one point he even predicted passage of the 2017 tax cuts. He closed the monologue by “wishing Donald Trump luck” and saying he would “give him a chance” while “demanding he give us one too,” on behalf of the “historically disenfranchised.”

However, Chappelle later confessed to not even remembering the statement but wishing he hadn’t said it after some misinterpreted it as support for Trump.

Chappelle is the 22nd person to receive the Mark Twain Prize for American Humor. Others include Richard Pryor, Julia Louis-Dreyfus, Eddie Murphy and Bill Murray.

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