Who died and made you boss?

Dean

Dean: You're family. I don't know if you've noticed, but me and Sam, we don't have much left. I can't do this without you. I can't. So don't you dare think about checking out. I don't want to hear that again.
Bobby: Okay.
Dean: Okay. Good.
Bobby: Thanks. Now, we done feeling our feelings? 'Cause I'd like to get out of this room before we both start growing lady parts.

You've got a whole Dr. Huxtable vibe coming off you. You're like... father material.

Sam

I'll pay you money if you sit still. This is like diffusing an IED with poop.

Dean

Old Dean: You saw a chance to turn the hands of the clock back and get out of that damn chair. Pretty tempting. I can imagine.
Bobby: No, you can't.
Old Dean: You got me. I never been paralyzed. But I tell you something--I've been to Hell, and there's an archangel there wanting me to drop the soap. Look at me! My junk's rustier than yours!

Dean: And by the way, how you doing?
Bobby: Doing?
Dean: Yeah. You know, just... in general.
Bobby: Oh, you mean my legs. I'm just weeping in my Haagen-Dazs. Idjit.

Don: She bakes cupcakes.
Dean: Yummy.

Sam: You just went. You didn't hesitate, because you care and that's who you are. Me, I wouldn't even think to try.
Dean: Yes you would
Sam: No Dean. I'm telling you. It's just better with you around.

Sam: Have you seen you? You look like...
Dean: ... the old chick in Titantic. Shut up.

How do you keep your lawn so green? C'mon Dean, you've never been what I call, Brady.

Yellow-Eyed Demon

Jesse: What, didn't your dad tell you about the Tooth Fairy?
Dean: My dad? My dad told me different stories

Sam: Oh, d-dude... that's not what I think it is, is it?
Dean: I got bored. That nurse was hot.
Sam: You know you can go blind from that, too.

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