So, what? You're like a DeLorean without enough plutonium.

Dean

What do I look like-Dr. Angel, Medicine Woman?

Dean

Dean: Well... this is it.
Sam: This is what?
Dean: Team Free Will. One ex-blood junkie, one dropout with six bucks to his name, and Mr. Comatose over there. It's awesome.
Sam: It's not funny.
Dean: I'm not laughing.

Michael: And you think you know better than my father? The one unimportant little man. What makes you think you get to choose?
Dean: Because I got to believe that I can choose what I do with my... unimportant little life.
Michael: You're wrong. You know how I know? Think of a million random acts of chance that let John and Mary be born, to meet, to fall in love, to have the two of you. Think of the million random choices that you make--and yet how each and everyone of them brings you closer to your destiny. Do you know why that is? Because it's not random. It's not chance. It's a plan that is playing itself out perfectly. Free will's an illusion, Dean. That's why you're going to say yes.

Anna: I need you to kill some humans.
Uriel: Always happy to do some smiting.

Dean: What exactly are we gonna march up there and tell 'em?
Sam: Uh, the truth.
Dean: What, that their sons are back from the future to save them from an angel gone Terminator? Come on, those movies haven't even come out yet.

Dean: Really? Anna?
Castiel: It's true.
Dean: So she's gone all Glenn Close, huh? That's awesome.
Castiel: Who's Glenn Close?
Dean: No one. Just this psycho bitch who likes to boil rabbits.
Sam: So, the... the plan to kill me--would it actually stop Satan?
Dean: No, Sam, come on.
Sam: Cass, what do you think? Does Anna have a point?
Castiel: No. She's a... "Glenn Close."

Sam: You still crazy?
Dean: Not any more than usual.

Dr. Cartwright: Why you?
Dean: Why me what?
Dr. Cartwright: Why do you have to hunt monsters? Why not let someone else do it?
Dean: I can't find anybody else that dumb.

Dr. Cartwright: I'm Dr. Erica Cartwright. I've been assigned to your case.
Dean: You're my shrink? Well, lucky me.
Dr. Cartwright: And you're my paranoid schizophrenic with narcissistic personality disorder and religious psychosis. Lucky me.

Dr. Fuller: You were referred to me by a Dr. Baber in Chicago.
Dean: That's right.
Dr. Fuller: Isn't there a children's book about an elephant?
Dean: I don't know. I don't have any elephant books.

Sam: Okay, last words?
Dean: I think I'm good.
Sam: Yeah, me too.
Dean: Here goes nothing.

Supernatural Season 5 Quotes

Dean: Where's Cass?
Chuck: He's dead. Or gone. The archangel smote the crap out of him. I'm sorry.
Dean: You're sure? I mean, maybe he just vanished into the light or something.
Chuck: Oh, no. He exploded. Like a water balloon of chunky soup.

Dean: Do I know you?
Becky: No, but I know you.