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 심장 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 수퍼내츄럴 im talking about 크리스마스 cottage,i think thats what its called,i mean i seen him crying alot in 수퍼내츄럴 but in the 크리스마스 cottage,he really broke out crying like...like...i can't explain it but it makes 당신 wanna break out crying,i almost did.