Three Things Grammy Voters Must Be Thinking in Order to Award Dave Chappelle Yet Again

The three kinds of voters behind Chappelle’s Grammy dominance
Three Things Grammy Voters Must Be Thinking in Order to Award Dave Chappelle Yet Again

Oops, he did it again. Last night, Dave Chappelle won the Grammy Award for Best Comedy Album for What’s in a Name?, his fifth win overall and third trophy in the past five years. Depending on your circle of pop-culture compadres, yet another win for Chappelle might have elicited cries of “What the heck? How do we keep handing awards to this guy?” I’m not here to decide whether another Grammy means Chappelle isn’t canceled after all (he never was), or to debate the merits of What’s in a Name?. Instead, given all the controversy that continues to circle the comedian, let’s engage in a thought experiment to determine what must go through the mind of a Grammy voter who checks the box next to Chappelle’s name. By my thinking, a Chappelle voter must fall into one of three camps.

The “Chappelle Is the Best” Crowd

Take away the controversy (I know), and you’re left with a comedian that many consider among the best ever to grab the microphone. Some faction of voters must be thinking, “I know what Chappelle says offends some people, but I don’t care. He’s simply a better comedian than Trevor Noah or Sarah Silverman. I’m going to vote for the best artist, not the least offensive one.” Think of it like the baseball Hall of Fame voter who casts a ballot for the guy who cheated on his wife or yelled at the fans — “I may not think Player X is the greatest person, but his talent/performance earned him the spot.”

The “I’ll Show the Snowflakes” Mob

The same gene that compels Chappelle to say whatever he’s not supposed to can be found in the DNA of a lot of artists. Create a rule and they feel duty-bound to break it. What some view as Chappelle’s insensitivity or even cruelty can be perceived as bravery by those who value artistic freedom above all else. That goes double for conservatives who bristle at the idea of “political correctness,” “woke speech” or whatever euphemism represents prohibition around certain kinds of comedy punchlines. A vote for Chappelle could be a middle finger extended to anyone who wants to restrict what a comic can joke about. 

The “Chappelle Is the Comedian I’ve Heard of” Gang

Who votes for the Grammys? According to the Recording Academy, voters come from “a pool of vetted and venerable performers, songwriters, producers, engineers, instrumentalists, and other creators currently working in the recording industry.”

Think about that for a minute. While there must be some comedians among the “vetted and venerable performers,” there are also jazz saxophonists, classical violinists and gnarly-bearded dudes who play the slide guitar. Then there are all the wonky producers and engineers — industry experts, sure, but possibly not folks who spend their spare time spinning comedy records. 

Just like the candidate with the most billboards usually wins your local alderman race, voters who don’t know much about the contenders will opt for the one with the most name recognition. “I’ve heard of that guy!” “I loved Chappelle’s Show.” “Chappelle keeps winning so he must be good.” 

Are there other reasons to vote for Chappelle? Let me know if you can think of one. Meanwhile, don’t blame me for his continued dominance at the Grammys. I would have voted for Wanda Sykes.


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