When Dave Chappelle stand-up specials are mentioned in barbershops, on street corners, or in blunt cyphers, 2000's Killing Them Softly is often regarded as his best. He was 27 years old, already a comedy veteran, with a cult classic film under his belt with Half-Baked. In a powder blue Triple 5 Soul button-down, Chappelle spoke in funny voices while making fun of white people that would later become a staple in his comedic routines.
This was three years before he would flip pop culture on its head with Comedy Central’s Chappelle's Show. The sketch comedy show would become so successful, that he suddenly quit the show, went AWOL and popped up somewhere in Africa. He’s been creeping back into our hearts and minds with random appearances at award shows, comedy clubs, and hosting SNL. Chappelle seems to be back now, at least as a stand-up comedian with three upcoming specials with two hitting Netflix next Tuesday.
While Killing Them Softly is regarded as his best, my favorite Chappelle stand-up special is 2004's For What It's Worth. He was more mature by then—in the growing pains of becoming the greatest comedian of his generation. Every joke landed, his white man voice was more polished, the punchlines were sharper. Chappelle's brilliance hasn't looked back since that special.
When I saw him live in 2013, I don't remember many of the jokes he told, I remember the energy in the audience. It was pure electricity, like we were watching Michael Jordan in mid-flight, or Michael Jackson moonwalking across a stage. The crowd had this nervous energy, not knowing what to expect because it was after his alleged meltdown during a show in Hartford, Conn. There was a constant stream of laughter as he stood there and talked and laughed with us.
Chappelle commands that kind of respect, that kind of awe and wonder. He's reached a point where his mere presence is a spectacle. His stand-up game has always been one of his best skills, making us laugh with his wiry frame and conversational delivery. He’s like your funny cousin, holding court at family get-togethers when he's on stage.
This vibe didn't change in the two of the three Netflix specials I had the liberty of catching Thursday evening. No one famous was in the small screening room I sat in, Chappelle wasn't there to take our questions, but I didn't care. I was anxious to see what one of my favorite comedians had up his sleeve again.
Most of the first special was based on events that happened in 2015 and 2016. He mentioned bombing a show in Detroit so badly, he went out afterwards and gave bubble gum to homeless people so they could be hungrier. He talked about each of the four times he met O.J. Simpson in the only way he can. One time in particular, he recalled telling one of his agents, “get over yourself,” after running into the Juice after the acquittal and emphasizing that Simpson rushed for over 11,000 yards.
He touched on how technology and information are desensitizing us, and how he flaked on a Flint, Mich. charity event because Chris Rock had an extra ticket to the Oscars. He also poked fun at himself for not being as monetarily successful as he should’ve been in a bit about when he took his son to see a Kevin Hart show. "I was furious," Chappelle screamed, painting a picture of his flesh and blood slapping his knee to Hart's antics on stage. "Nigga, I tell jokes, too!" Unsurprisingly, everything hit.
That's until he started making jokes that will certainly make people uncomfortable in our current PC reactionary culture. Chappelle poked fun at white women and white gay men’s claims of discrimination by driving home the point that it still doesn't compare to the ways black and brown people are treated in this country. He also mediated on Bill Cosby’s rape allegations as he tried to come to grips with them as a black comedian who looked up to Cosby.
He compared the Cosby situation to chocolate ice cream. Let me explain. As a black comic, Chappelle noted that Cosby had a huge impact on his career. He asked the crowd, "How would you feel if chocolate ice cream raped people?"
He felt torn about Cosby's fall from grace and started rapping off all the good Cosby has done like being the first black comic to win an Emmy or his various college funds, among other things. Chappelle said that Cosby's like a superhero that goes around town asking women if he can pat their vaginas in order to gain power to save people. The catch is, if said women refuse, he's forced to rape them. Essentially, the punchline was how Bill saved more than he raped. Despite it’s obviously squeamish nature, that joke hit too.
The first installment felt more like a comeback, stand-up comedy , even with some of the topics feeling dated. The second one felt more like a primer for something bigger and new—more lighthearted with jokes about masturbation and marriage. He also looked back at new hecklers—touching on the time a man threw a “premeditated” banana peel at him in Santa Fe.
The genius stand-up comics always make us uncomfortable. George Carlin challenged our personal views, Richard Pryor did the same with the same conversational style Chappelle has, Eddie Murphy did with his vulgar delivery. I believe Chappelle is in that conversation—frankly, he has been for years. He's this generation's most influential and important comic. Even his own influence isn't lost on him. At one point, Chappelle mentioned how he had to watch Key & Peele make his show everyday. This isn’t new, he took this same shot at the comedy duo last year at the Roots Picnic saying, "Put some respect on my name. Y'all don't know what I've been through, watching Key & Peele do my show the last five fucking years."
The ability to be important in two mediums is rare for a stand-up comic. Only a few are able to be legends in two games. I’m not sure if he’ll ever get back into movies or television, but Chappelle’s current stand-up run is that of the goats. I can only imagine how ridiculous the third installment of this series is going to be. Whatever the case, your face will hurt, tears will fall, and you will feel tremendously uncomfortable because Dave Chappelle is the king.