Sam: What if you guys lead the devil to the edge, and I jump in?
Bobby: Sam...
Sam: It'll be just like when you turned the knife around on yourself. One action, just one leap.
Bobby: Are you idgits trying to kill me? We just got done talking your brother off the ledge, now you're lining up to say yes... This isn't an option, Sam.

Dean: [wearing a surgical mask] Hey, I looked like the King of Pop.
Sam: [Rolls eyes]
Dean: Too soon? Too soon.

And you keep an eye on Norman Bates here.

Dean

Lucifer... you are my brother, and I love you. But you are a great big bag of dicks.

Gabriel

We can either take on the Devil together, or you lame-ass bitches can eat me. Literally.

Dean

Baldur: You think you own the planet? What gives you the right?!?
Lucifer: No one gives us the right. We take it.

Kali: I never took you for the type.
Gabriel: Romantic?
Kali: Pathetic.

But... me and Kali, we, uh... had a thing. Chick was all hands.

Gabriel

Dean: So, screw destiny right in the face. I saw we take the fight to them, do it our way.
Sam: Sounds good.

Dean: Where the hell are we?
Castiel: Van Nuys, California.
Dean: Where's the beautiful room
Castiel: In there.
Dean: The beautiful room is in an abandoned muffler factory in Van Nuys, California?
Castiel: Where'd you think it was.
Dean: I-I don't know. Jupiter. A blade of glass? Not Van Nuys.

Word to the wise. Don't piss off the nerd angels.

Dean

So you know you can't trust them, right? You know Sam and Dean Winchester are psychotically, irrationally, erotically codependent on each other, right?

Zachariah

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.