This is more of a general comment, not really about Chappelle. It's not about the person they make fun of, it's how they do it.
>hurr trump's so self-centered he makes videos of himself masturbating and masturbates to that
>lol what was more smashed after the election, hillary or her blackberries
>donald does his hair with a cotton candy machine
These are fine for me because they have a kernel of truth to them that anyone can honestly acknowledge.
Trump is definitely self-centered, whether it's legit or a schtick.
Hillary probably got tanked after the election, like she spent a billion, everyone told her she already won, and she lost it all to fucking Donald Trump. Also it's a matter of established fact that her blackberries were smashed with a hammer. These are all probable and realistic and it doesn't require you to buy into a premise that makes you a bad person for supporting your candidate.
But instead they go for the dumbest humor that requires you to buy into a premise antithetical to your candidate in order to find it funny.
>duh huh Drumpf's a fascist
> dude lock her up LOL
>blumpf's blood pressure is kremlin over racist, impeach 45!
Not only is it dumb, not only does it require you to buy into a nebulous premise, you also have to hate your candidate to find it funny. It's malicious humor, it's being done out of pure disdain for the person being lampooned. They're walking right over the Lampanelli rule; never make fun of someone you actually hate, it will seep through and be obvious no matter what, and it will kill the funny.
Except in this instance it only kills the funny for the people outside the filter bubble. For the ingroup laughing at the joke, it's not even hearty, genuine laughter. It's the practice of a cult mindset, the conscious weaponization of humor as a vehicle for ridicule against a certain person or idea that is considered double plus ungood. It's a practice to reinforce their collective loathing of the person.