There is 2 for me and that is when dean dies in no rest for the wicked so sad may I add my dean dying like that!!! and in the episode Heart when he has to shoot madison that was sad even dean shed a tear
Just my opinion but i think his best crying moment is when,..i think he was apologizing to this painter,i know im not talking about supernatural im talking about christmas cottage,i think thats what its called,i mean i seen him crying alot in supernatural but in the christmas cottage,he really broke out crying like...like...i can't explain it but it makes you wanna break out crying,i almost did.