There's nothing quite like seeing a manly man cry to make me choke up. There have been episodes of Supernatural where I could barely see the TV screen through tears, and Jared and Jensen always manage to make those scenes seem very real -- not overacted at all. Some of the ones that got to me:
1. "Heart" -- This one is probably the most heart-wrenching for me, despite the fact that Sam hadn't known Madison long. He'd finally allowed himself to feel something for a woman again, only to lose her. And the fact that he had to be the one to kill her, that she asked him to because she knew the beast she harbored inside...man, how awful. It was extra awful because Madison, in her human phase, was a good person.
2. "No Rest for the Wicked" -- After an entire season of desperately searching for a way to get Dean out of his deal with the demon, Sam has failed. He cries as he holds his dead brother in his arms.
3. "On the Head of a Pin" -- At the end of the episode, Castiel reveals that Dean broke the first of the 66 Seals and that he has to be the one to stop Lucifer. With tears in his eyes, Dean tells Castiel he can't do it, it's too much, he's not strong enough. You get the feeling that this might be the moment that Dean finally cracks from too much pressure, too much bad stuff and responsibility for mankind's welfare.
4. "Heaven and Hell" -- When Dean tells Sam about his time in hell.
Dean crying moments:
What teary moments have gotten to you?
