I have never found David Chappelle funny.
I spent the majority of my high school hearing peers in High school yell "RICK JAMES B!TCH!" at each other and howl with laughter, never seeing it as I did not have cable during those years. Finally saw the skits in college and it was lazy humor IMO. Same way his "Black Bush", "Niggar Family", and other sketches were in my eyes. Definitely proved to be popular though. ****, the Boondocks even sold out their original humor to follow in its path of lazy race jokes hidden as social commentary.
My girlfriend forced me to watch the special and it was....meh, same as I've always seen him. Observations, funny if you can see his plain and juvenile view, and meh for the rest. Nothing timeless like Murphy's "Delirious". Chappell also doesnt live an exciting enough life to ever create something later in life as wild as Redd Foxx's "Racy Tales" or "Pass the apple Eve". He lives as a family man in Rural Ohio. So what you are left with is an aging, and at this point, second-best Kevin Hart(whose recent special also is the antithesis of funny while we are on the subject) who now holds relevance with an audience that remembers him for being the edgy funny man of their youth. Same way 80's babies who remember Kel with such rose-colored glasses while cringing at the sight of Keenan still laughing at his own jokes, and flubbing lines after a decade of being on Saturday Nigh Live.