For me it wasnt a specially pitiful moment of Chris at all, but I guess that it piled up on me over the time...
When he released the hamburglar video I felt sorry for him making such an ass of himself and PMed him on youtube warning him that Jackie was a troll. I tried to proof it and at the same time give him some tools, by showing him the tineye (reverse image search engine for those you dont know) results for Jackie's photo.
We all know how well it resulted
I never pitied him anymore for any specific event, not even Bob's death (He was pretty old, so it was expected....not that Chris expected it because of stupidity but still...) but I generally pity him for how all of the things that form his self image are a lie:
-He thinks he is one of the good guys (fuck that, he is THE good guy!) but while he is not Hitler, he still is a terrible person.
-He never had any real, meaning friendship, but he thinks he did/do because he doesnt know any better.
-He thinks Sonichu was a hit back in the day and that he is an amazing artist and storyteller when even a somewhat talented elementary school kid would do better than him.
-He thinks he had real relathionships (although by internet) with women, while in reality no woman ever liked him and no woman will.
-He thinks he is handsome and that his voice sounds like Sinatra's.
-He thinks that he is superintelligent because of HONOR ROLL, but most probably he got honor roll just because being autistic and all evidence shows that even with autism aside, he is profoundly stupid.
-Pretty much everybody that ever praised or humored him was either a troll or some well meaning individual praising him because people never expected anything of him.
Not going to happen, but if by some miracle he someday sees the truth about of all this...it wont be pretty, and that makes me pity him.