

Humor is difficult.
It’s tough when it’s actually a bad joke or they are telling it badly, but they find it funny.
If it’s a genuinely funny situation / retelling, both of you laughing about the same thing and also about how the person in question is struggling to breathe because they have to laugh so much, that’s funny.
But it really really really depends.
He does content? He can be a bit aggressive about his topics, that can rub people the wrong way.
I don’t think he did anything offensively, legally or morally wrong.
I know just he exists, I don’t follow his content.