I seems to be a very emotional person. I think the crying is just an expression of his own anger with himself. Despite the depression he only felt good things around you and your family. He really seems to love them. He definitely seemed to have a connection with your mother. He was like a son to her. So try to be supportive for her as well. She is taking this hard. I can't really tell if your father is around or stepfather, some sort of father figure. They tried to bond but he was always a bit distant because how his own father was. But I do think they had warmed up in the last few months. I see them playing pool or cards I think, something around a table like thing. I think both of them could be a bit emotionally distant. Your father or father figure seems to struggle a bit with this and he hides it. Maybe try to have a day where you can talk about good memories or funny memories about your friend. I feel like you have been friends for a while. I feel closer to middle school to high school range you guys met and he hung out a lot at your house not wanting to go home.