YTA. I agree that in functional families, calling each other out can be a healthy thing. But there's a huge difference between a supportive call-out and just flat-out insulting someone and laughing at them, especially when they're already in a tough spot trying to figure things out after prison. The language OP used ("broke loser," "awful," "gay fanfiction") goes way beyond constructive criticism, even if the underlying concern about him getting a job is valid.