Silverman had already found herself, and influenced a generation of comedy in the process. However, their shifts now seem like a breakthrough point in the process of finding themselves artistically. It’s not without precedent in the history of comedy: George Carlin and Richard Pryor, for example, shed popular personas in the pursuit of something greater. It might seem small - “you told one type of joke, now you tell another” - but it’s arguably closer to an athlete going from basketball to baseball than a musician going from guitar to piano. Sarah Silverman’s ability to shed her deeply ironic character for something more genuine and surprisingly spiritual is one of the greatest achievements in comedy over the last decade.
Based on that, Chappelle makes this list, warts and all. There was a ton of funny comedy put out this year, but I was looking for specials that were the most distinct and specific to the person creating them. With stand-up specials being released at an unprecedented clip, I find myself judging them based on the singularity of the viewing experience. I honestly didn’t expect him to come back this good.
Chappelle is an all-time master of bringing an audience in - talking slowly, growing serious and personal - and using that intimacy to dispense completely unexpected, deeply silly punch lines. It helps that the chunk is surrounded by some of the most structurally interesting stand-up, well, ever. You won’t necessarily laugh, but it does challenge you to wrestle with your expectations of Chappelle, and of comedians in general. During the worst part of the hour, Chappelle subtly turns that spotlight on himself by forcing the audience to reckon with his own more ignorant material. It’s not about passing judgement, as much as about coming to terms. The show is about reconciling the bad behavior of good men and the good behavior of bad men, whether it’s O.J. Yet upon rewatching, those jokes - particularly in Age of Spin - do strangely fit. It’s not just that most of Chappelle’s jokes about LGBTQ issues were bad because his opinion was wrong they were also bad jokes: sloppy, poorly thought-out, unoriginal. When Dave Chappelle released his two Netflix specials The Age of Spin and Deep in the Heart of Texas earlier this year, after famously spending time away from the spotlight, it was the biggest event in comedy - and together they represented some of the absolute best and worst stand-up that we saw in 2017.
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