If the old man's Kermit, whose hand's up his ass?

Dean

I've seen some stupid in my time, but you, you take the crown. Putting Jaws in a fish bowl? How do you think it's going to end?

Dean [to Samuel]

I don't care if you've got soullessness or the freakin mumps. You know better than this!

Dean

I don't trust him. Dude's hiding something. I can feel it and if you weren't Robo-Sam, you'd feel it too.

Dean

Samuel: This Castiel? You're scrawnier than I pictured.
Castiel: This is a vessel. My true form is approximately the size of your Chrysler Building.
Dean: All right, all right, quit bragging.

Gramps threw a barbeque and left us off the e-vite list?

Dean

Dean: I'm sorry. I'm sorry, one more time. Like I'm five. What do you mean he's got no...
Castiel: Somehow when Sam was resurrected, it was without his soul.

Woman: I'm sitting like this so you'll look at my breasts. I just bought them. I need a lot of attention.
Dean: Good luck with that.

Ever since I came back, I am a better hunter then I've ever been! Nothing scares me anymore, because I can't feel it. I don't know what's wrong with me. I think I need help.

Sam

Bobby: Did you know my first girl turned out to be a...
Dean: [hangs up] whoa, no.

You know what else? I get a pedicure once in a while.

Bobby

Tori Spelling. I'm a huge fan. Girl's a real talent.

Bobby

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