Trickster/Gabriel: Where'd I screw up.
Sam: You didn't. Nobody gets the jump on Castiel like you did.
Dean: Mostly it was the way you talked about Armageddon.
Trickster/Gabriel: Meaning?
Dean: Well, call it personal experience. Nobody gets that angry unless they're talking about their own family.
Sam: So which one are you? Grumpy, Sleepy, or Douchy?

Dr. Piccolo: Doctor, seriously.
Sam: What?
Dr. Picolo: Seriously, you are brilliant, you know that, and a coward. You're a brilliant coward.
Sam: Uh, what are you talking about?
Dr. Picolo: As if you don't know.

Dean: Ally with the Trickster?
Sam: Yeah.
Dean: A bloody, violent monster... and you wanna be Facebook friends with him? Nice, Sammy.

You sorry sons of bitches. Why do you think you two are the vessels? Think about it. Michael, the big brother, loyal to an absent father. And Lucifer, the little brother, rebellious of daddy's plan. You two were born to this, boys! It's your destiny. It was always you. As it is in Heaven, so it must be on Earth. One brother has to kill the other.

Trickster

Dean: Well, you sure look lovely tonight. Especially for a dead chick.
Latisha Actress: Buddy, I have heard that line 17 times tonight, okay? And all from dudes wearing MacGyver jackets. But you seem different.
Dean: How so?
Latisha Actress: Well, you don't seem scared of women.

So what does the future hold for Sam and Dean? Well, uh, how do you feel about angels? Yeah. you know, because let me tell you, they're not nearly as lame as you think.

Chuck

Dean: Okay, and why exactly would you want the Devil dead?
Crowley: It's called survival. But I forgot you two are at best functioning morons.
Dean: You're a functioning... morons... moron.

Lucifer: Castiel, right? Castiel. I'm told you came here in an automobile.
Castiel: Yes.
Lucifer: What was that like?
Castiel: Um, slow. Confining.
Lucifer: What a peculiar thing you are.

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

Dr. Fuller: You were referred to me by a Dr. Baber in Chicago.
Dean: That's right.
Dr. Fuller: Isn't there a children's book about an elephant?
Dean: I don't know. I don't have any elephant books.

Anna: I need you to kill some humans.
Uriel: Always happy to do some smiting.

Dean: Cherub?
Castiel: Yeah, they're all over the world. There are dozens of them.
Dean: You mean the little flying fat kids in diapers?
Castiel: They're not incontinent.

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