I'd say a few saddest moments for me....
1. HBK's send off...
How can anyone NOT shed a tear?! He worked his azz off in that match the night before in WM26 with Undertaker and he is and has been the epitome of entertainment to me as long as I've been watching, ever since I was little (and I'm going on 31 now.) The song that played during the video memories...the lyrics "The show is over...say goodbye..." Ahh...
Then he gets to tell his wife and kids that he's coming home and said "Ladies and Gentlemen, HBK has left the building.." and he has his moment with HHH, and leaves his glowstix in the shape of an X as a tribute to DX. I was in tears the first time, and watching any replay of that, I still start bawling my eyes out.
2. Matt Hardy turning on Jeff Hardy...
I was shocked when he cost him his title at the PPV Royal Rumble (08 or 09?..I can't recall.) But then all the little times he kept showing up and calling him out on Smackdown. OMG...
Right after Jeff's house burned down, and his dog died. When Matt showed up with the dog collar that used to belong to Jeff's dog...I was so like thinking "U $%#%, that was like Jeff's kid..." I was so caught up in the emotion, and then when they built up to the WM 25 match with that Decyfer Down song "Crash" that just really captured the emotion and the deceit...I just could feel the empathy.
3. HBK's first farewell speech...
The Tell Me A Lie..man..that gets me weepy. Then you top it off with the classic..."I've lost my smile..." I mean...if that doesn't get you..then you have no heart.