No drinking, no gambling, no pre-marital sex. Dean, they basically just outlawed 90% of your personality.

Sam: Dad said they always had the perfect marriage.
Dean: It wasn't perfect until after (Mary) died.

Sam: Heaven?
Dean: Yeah.
Sam: Okay, how are we in Heaven?
Dean: All that clean living, I guess.

Unleash the Kraken. See you tomorrow morning.

Sam: Dean, enough!
Dean: What?
Sam: You just punched a Cupid!
Dean: I punched a dick!

Dean: Where am I going?
Sam: Dean, it's Valentine Day. Your favorite holiday, remember? I mean, what do you always call it - uh, Unattached Drifter Christmas?

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.

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.

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

Sam: Oh, hey, Chuck, look. If you really want to publish more books, I guess that's okay with us.
Chuck: Wow. Really?
Sam: No, not really. We have guns and we will find you.

Supernatural Quotes

Why do they call this place The Empty? It's full. It's full of sorrow and despair playing over and over again of angels and demons dreaming about their regrets. Forever.

Ruby

Weird, creepy, off-the-grid "Children of the Corn" people? Yeah, I’m in.

Dean