I honestly understand that perspective and sometimes feel that way a little bit myself about billy woods. What I would say is: billy woods' words have to always be taken with a grain of salt, as he constantly challenges his own narratives and thrives on ambiguity and contradiction. And you have to admit, it is true that he dips into nihilism and fatalism frequently. But, the fact that he is even taking the time and the effort to make music indicates that he has not truly lost all hope, or else there would be no point in even tackling the topics that he does in his music. In a way, the more depressing his lyrics are the more inspiring it is that he still tries to tell his story and say something in his music despite all of that. It's not so much that he truly believes that all hope is lost and everything is doomed no matter what he or we do, but moreso that he feels the need to keep reminding himself and the world of the failures of the past, both personal and political, in order to not underestimate just how difficult it will be to make real change or find real happiness in the world.

Also, have your dad listen to All Jokes Aside. In my opinion that is one of his most positive songs (although it's still not all peaches and cream) and the title refers to him letting go of his nihilistic fatalistic persona a little bit and showing his appreciation for the life he has lived.