The sort of roast humor where you make fun of people on purpose has always confused me. It feels much the same as traditional masculine humor centering around insulting people. I'm told it's supposed to be funny, but I don't get humor very well anyway, and I've never gotten masculine insult humor.
To me it sounds more like jockeying for dominance than something to laugh at. When a bunch of guys get together and start start throwing insults around and laughing, all I want to do is cringe and go hide in a corner.
I don't get why it's necessary. and when somebody says that somebody else crossed the line, I'm usually like yeah I thought everyone was over the line like 3 hours ago. Sigh.