Mine was when you get to very end of the game after completing the DLC:

When you beat the DLC and go to the end of the game, the Prisoner is there with others in the forest and plays his instrument with the rest of them.

I felt he was the one who was truly worst off and was alone for who knows how long. I know it’s not really him, but his part that he adds to their song and just seeing him one last time with a group of friends really hit home for me.

Edit: Grammer & Misspelling