Trump tricks and transgender jibes sully the Chappelle experience

“Even the sun goes down and heroes eventually die,” goes the Outkast song Aquemini. After ploughing through the recently released Netflix pair of stand-up specials (a third is coming), The Age of Spin and Deep in the Heart of Texas, from actor and comedian Dave Chappelle, I am reluctantly admitting that time heals and, when necessary, kills all in its wake.

Chappelle is seemingly a man buried alive by time and enjoying the fruits of his celebrity status more than raising the bar on our understanding of race relations, as he did on the two specials, HBO’s Killin’ Them Softly (2000) and Showtime’s For What It’s Worth (2004).

In The Age of Spin, Chappelle is hanging out with rappers (apparently Danny Brown and crew), smoking their weed and getting booed on stage. We know this because he tells us so, as part of an anecdote about being heckled by fans. Chappelle is getting stopped by the police along with a drunk, self-appointed designated driver he meets while hanging out in Hollywood. But because he is Chappelle, and the Breathalyser does not pick up weed, he is free to go, but not before his friend gets arrested.

Chappelle, because of his fame, now has Chappelle privilege, putting him in a bracket above the average black dude on an American street.

Soon after this, Chappelle relays a story of him going to a Hollywood party, an afterparty for the Oscars, and admits to getting “seduced by Hollywood” all over again. This is where things start to hurtle downhill. Asked by a pair of producers whether he has any ideas he’d like turn into films, Chappelle fumbles, because he is caught off-guard, then recovers to make up a story about a gay superhero who can’t access his power unless he touches a few women on the vagina.

Now, our superhero is a little bit ugly, he is having a hard time finding women who can appease his request, so he simply rapes them. If the gay superhero sounds a little like sitting United States President Donald Trump, and we can’t figure out why he is being obfuscated, except for the giveaway “pussy grabs”, it may be pointing to Chappelle’s changing sense of holy cows.

For a man whose comedy carries such a political charge, in The Age of Spin Chappelle acts like Trump never happened and spends way too much time having a laugh at the expense of Caitlyn Jenner, whom he calls Bruce Jenner, and other queer people. Transgender people get it the worst. They are apparently the gangsters of the LGBTI (lesbian, gay, bisexual, trans, and intersex) world, heading out into the club to “trick niggas into fucking us”.

Chappelle frames his set around a recurring motif of the four times he met OJ Simpson, using it to resolve his feelings about Simpson’s guilt or innocence. There is also the small matter of Bill Cosby, “the Steph Curry of rapes”, after more than 50 women accused him of sexually violating them. Chappelle is surprisingly ambivalent about Cosby, or at least tries to weigh up his evils against his altruism, reaching the conclusion that because of the number of black children he has helped get to college, “he saves more than he rapes, but he still probably rapes”.

Granted, Cosby’s situation is one in which these are all allegations at this stage. But my concern with Chappelle is more about what he avoids speaking about and why that may be so in the first place.

Perhaps the anecdotes about going to Kevin Hart’s show with his son may shed some light. Chappelle watches, with a tinge of envy, the relatively larger success of peers such as Hart. As he warmly welcomes Chappelle and his son backstage, Chappelle jokes that Hart’s banquet table was like Sunday lunch on a Tuesday night — a reference to a bigger rider budget and therefore bigger clout.

In The Age of Spin, Chappelle is constantly trading on his outsider status, juxtaposed with the weight of his brand. What he doesn’t realise is that whatever remains of his outsider status no longer denotes edge and hipness.

But Chappelle is also playing a game of setting himself apart from the queer-led Black Lives Matter generation, with clear machismo posturing, as though he is rewriting his legacy from scratch.

In Deep in the Heart of Texas, the second of the specials, first filmed in 2015, Chappelle is a little more strident and nuanced in his dissection of the race question in the United States. But a tale about a confrontation with four white racists in his home state of Ohio ends inconclusively, with Chappelle asking to be fellated by the mother of one of the four teenage racists.

Chappelle seems to be interested in a discussion about semantics and political correctness, but later confesses to not being ready to change up his whole pronoun game. “Nigga is a pronoun” as far as Chappelle is concerned. In other words, “tranny” and “faggot” are hardly worthy of offence and outrage.

In the years since Chappelle walked away from the successful Chappelle Show during its third season, the figure of $50-million was thrown around as the amount Chappelle had turned his back on, apparently on the principle that he was losing control over the tone and direction of the series. Crucial for Chappelle, who had been raised on the principles of black nationalism, was how not to push the black stereotype beyond the point of redemption.

It was a dance Chappelle had been perfecting since his early stand-up routines in his teenage years, a formula whose strictures he’d break time and again in Hollywood, notably with the dismal white friend/ black friend cliché of Buddies.

In an episode of the Chappelle Show in which Chappelle appears in blackface as a minstrel character, he remembers that the laugh of a white crew member, in which he felt laughed at rather than laughed with, was a catalyst in his decision to quit the show and rethink its ethical direction.

There were also tensions between the show’s cowriter, Neal Brennan, a long-time white friend who perhaps did not mirror some of Chappelle’s concerns around the nuances of race. In the end, how Chappelle conducts his own career as a comic is his own prerogative. But the figure of $60 000 000, or better yet, the idea of “walking away from $50 000 000 and coming back for $60 000 000”, as he boasts in The Age of Spin, is symbolic in that it raises the question: Coming back to what?

This is not to decapitate Chappelle with the guillotine of political correctness, but with his two recent specials, Chappelle’s gags fail to occupy that space beyond the punchline. That space where our collective history lives. Where our creativity elevates us beyond the lies told about our supposed lack of humanity. The space of intersectionality. The space where there is no hierarchy of struggle.

Looking at the sizes of the venues (arena-like) and the colour of the audiences (mostly white) that Chappelle performs to nowadays, it is easy to imagine why he would shoot for the lowest common denominator. Big money Dave seems outside of himself and safe, a likely poster boy for Trump’s strange new America.

Concerned about whether I was reading the return of Chappelle incorrectly, I turned to a colleague for some answers. She said, through the filter of yesterday, we probably didn’t realise that Chappelle is the same man he always was. It is perhaps the movement of time that is rendering him antiquated. Indeed, it is up to the individual to decide what to do when the idols of our youth fall away.