Season 4, Round 3
Castiel: I'm the one who gripped you tight and raised you from perdition. -- Yes, yes you are.
Dean: Y'know, I finally get why you and Dad butted heads so much. You two are practically the same person. I mean, I worshiped the guy, I dressed like him, I acted like him. I listened to the same music. But you are more like him than I will ever be. And I see that now.
Sam: I'll take that as a compliment.
Dean: You take it any way you want. --
I'm pretty sure it makes me a bad person but I didn't like Dean begging his mom in that scene. I get why he did it. But if you're going there, go there. Tell her what she really needs to know.
Sam: Dude, you're confusing reality with porn again. -- Hardest choice in this round... I'm going porn.
Bobby: You stupid, stupid son of a bitch! Well, boo hoo! I am so sorry your feelings are hurt, princess! Are you under the impression that family's supposed to make you feel good, make you an apple pie, maybe? They're supposed to make you miserable! That's why they're family! -- Damn, recent conversations make me realize I really don't like the boo hoo. I'm okay with Bobby calling Dean a stupid son of a bitch though. He can be. But end of this quote, well it still wins overall for me.