Sam: Have you seen you? You look like...
Dean: ... the old chick in Titantic. Shut up.

Hit it, Mr. Wizard.

Sam

Sam: So we tell him the truth.You say Jesse's destined to go dark side--fine. But he hasn't yet. So if we lay it all out for him... what he is, the Apocalypse, everything - he might make the right choice.
Castiel: You didn't. And I can't take that chance.

Castiel: (sits on a whoopee cushion) That wasn't me.
Dean: Who put that there?

Jesse: What, didn't your dad tell you about the Tooth Fairy?
Dean: My dad? My dad told me different stories

Sam: Oh, d-dude... that's not what I think it is, is it?
Dean: I got bored. That nurse was hot.
Sam: You know you can go blind from that, too.

Dean: Yeah, everything Jesse believes comes true. He thinks the Tooth Fairy looks like Belushi, uh, joy buzzers really shock people, boom that's what happens.
Sam: Yeah, but convince him that joy buzzers don't actually work and they go from killer machines back into crap toys.
Dean: Probably doesn't even know he's doing it. How is he doing it?

Sam: Dude, what the hell?
Dean: I had a hunch I went with it.
Sam: You risked my ass on a hunch?
Dean: You're fine. Besides now we know who's turning this town into Willy Wonka's worst nightmare.

I'm Agent Bonham, this is Agent Copeland.

Dean

Dean: Not a word.
Sam: Dude, you just got whaled on by Paris Hilton.

Dean: Let me get this straight. Your, uh, ultimate hero was not only a short man in diapers, but he was a fruitarian.
Sam: That's not the point.
Dean: That is good. Even for you, that is good

Dean: Is that Gandhi?
Sam: Yeah!
Dean: Dude, he's squirelly.

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.