Dean: Tell me something; you keep saying we're gonna trap this guy, but isn't it kinda like trapping a hurricane with a butterfly net?
Castiel: No, it's harder.

Dean: Where've you been?
Castiel: Jerusalem.
Dean: Oh. How was it?
Castiel: Arid.

Eat it, Twilight!

Dean

So, pit stop on Mount Doom?

Dean

Honestly, people don't need a reason to kill each other. I mean, you seen the Irish? They're all Irish.

War

Dean: You're gonna go out there again?
Sam: Well, crap doesn't hit the fan with coffee breaks.

Dean: God?
Castiel: Yes.
Dean: God?
Castiel: Yes. He isn't in Heaven. He has to be somewhere.
Dean: Try New Mexico. I hear he's on a tortilla.
Castiel: No, he's not on any flatbread.

What's it been, like three days now? We got to cheer (Bobby) up. Maybe I'll give him a back rub.

Dean

Bobby: You are nine kinds of crazy, boy.
Dean: It's been said.

What if we win? I'm serious. I mean, screw the angels and the demons and their crap Apocalypse. They want to fight a war, they can find their own planet. This one's ours, and I say they get the hell off of it. We take 'em all on. We kill the Devil. Hell, we even kill Michael if we have to, but we do it our own damn selves.

Dean

Sarah/Lucifer: I'm not your wife, Nick. I'm an angel.
Nick: An angel?
Sarah/Lucifer: My name is Lucifer.
Nick: Sure. Naturally. Umm... could you do me a favor there, Satan, and remind me to quit drinking before I go to bed?

Castiel: You two need to be more careful.
Dean: Yeah, I'm starting to get that. Your frat brothers are bigger dicks than I thought.

Supernatural Season 5 Quotes

Endings are hard. Any chapped-ass monkey with a keyboard can poop out a beginning, but endings are impossible. You try to tie up every loose end, but you never can. The fans are always gonna bitch. There's always gonna be holes. And since it's the ending, it's all supposed to add up to something. I'm telling you, they're a raging pain in the ass.

Chuck

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.