Imo if it’s done out of a true intention to make someone laugh, even if it fails, it’s ok. I remember Jim Norton and Anthony joking about the Lacey Peterson and it was legitimately hilarious even it fucked up.
Some stuff is done or said for cheap shock value as some sort of performance with no real intention to be funny; that sort of thing I find stupid as fuck.
A lot of people seem to get a kick just out of being assholes and hide it behind some half assed attempt at “comedy”. Like when Ari Shaffir said after Kobe Bryant’s death “Kobe is GONE thank god that rapist died” and then tried to pass it off as some sort of comedy attempt, even though it didn’t seem like there was any attempt at a joke, just trying to piss people off. Seemed to me like he was just being a pos and hiding behind it, and I’m not even a basketball fan or really care about the topic at all.