Dave Chappelle, John Cleese and the New/Old Generation Gap

There was a time, not so long ago, when teenagers would have found the prospect of their high school naming a theater after alum Dave Chappelle mind-bogglingly awesome, particularly if it were accompanied by a visit from the legendary comedian. 

Why wouldn’t they geek out? Chappelle’s Show made its star and co-creator the hottest, most beloved and important funnyman on the planet. Quitting Chappelle’s Show at the height of its influence and popularity made him a goddamned folk hero, a funnyman of unimpeachable integrity who walked away from tens of millions of dollars and superstardom rather than compromise or corrupt his art. 

Then Chappelle had the poor judgement to become comedy’s answer to J.K. Rowling: a towering cultural figure who took a terrible wrong turn somewhere and became a professional bigot who has made transphobia the inexplicable core of their public persona. 

So when Chappelle returned to his old high school recently to talk to students the kids treated him not as a hero of free speech or bold, brave truth-teller but rather as a deeply problematic multi-millionaire who has used his power to defend his buddy Louis CK, insult the women who spoke out against CK and proclaim himself a proud TERF. 

The students were, of course, not allowed to record what Chappelle said during his talk, as their cell phones were confiscated and put in pouches, but it seemed to have gone about as badly as possible. 

Empowered by the times and the democratizing effect of social media, queer students challenged Chappelle on his words and actions and were treated to what appeared to be an appalling display of arrogance, narcissism, pettiness and resentment. 

The smartest, hippest, fastest man in any room had devolved into a preening show-business phony annoyed that stupid, powerless, extremely non-famous kids had the audacity to confront him on his transphobia just because he has continuously doubled down and chosen the path of “more transphobic” rather than less transphobic.

It was a tragicomic but mostly just tragic representation of the new generation gap, where the rebels and truth-tellers of the past broadcast their contempt for young people for being insufficiently deferential. 

Across the pond, John Cleese preemptively blacklisted himself from an appearance at Cambridge, tweeting “I was looking forward to talking to students at the Cambridge Union this Friday, but I hear that someone  there has been blacklisted for doing an impersonation of Hitler. I regret that I did the same on a Monty Python show, so I am blacklisting myself before someone else does.”

The statement was quintessential late-period Cleese: unfunny, self-pitying, self-aggrandizing and filled with a delusional conviction that asking comedians and artists to be more sensitive is tantamount to stifling free speech and silencing anyone who doesn’t tow the party line. 

What these arrogant former funnymen, along with Bill Maher and Ricky Gervais, share is an ugly, egotistical rage that they are now being challenged and confronted by teenagers and twenty-somethings they consider their cultural, creative and intellectual inferiors.

Disasters like Chappelle’s visit to his old school illustrate that despite his words, he does not want to have a conversation with his critics and detractors, particularly if they’re high school kids. Instead he wants to be treated with a level of respect befitting his tremendous wealth and fame and accomplishments.

Chappelle was so angered that these passionate, idealistic young people would have the audacity to judge him on the basis of his words, ideas, attitudes and convictions that he decided to judge them and find them lacking. 

Chappelle’s representative Carla Sims reported that Chappelle gave the children who criticized him an “F for forgiveness” but insisted they be given “some space to grow. They are going to say things that are immature.”

In actuality it’s Chappelle who needs to work on forgiveness and grow. He’s going to say things that are immature but that’s to be expected when you’re a forty-eight year old who has seemingly achieved anything a comedian possibly can, and now seems intent on spoiling all that he’s accomplished for the sake of a toxic political agenda. 

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