Season 2, Round 1, Bracket #2/4:

Dean: Sam, you and dad, you’re the most important people in my life. And now... I never should have come back Sam, it wasn't natural, and now look whats come of it. I was dead and I should've stayed dead. You wanted to know I was feeling, well thats it. So tell me, what could you possibly say to make that alright?

vs

Dean: Sammy's always getting a little J. Love Hewitt when it comes to this.

Sam: Come on Dean, not now! We were just starting to be brothers again.

vs

Sam: Dean, you're my brother, alright? So whatever you're carrying, let me help a little bit.

Dean: My name is Dean Winchester. I'm an Aquarius, I enjoy sunsets, long walks on the beach and frisky women. And I did not kill anyone. But I know who did. Or rather "what" did. Of course, it can't be for sure, because our investigation was interrupted. But our work in theory, is that were looking for some kind of Vengeful Spirit.

vs

Sam: Elroy McGillicuddy? John: And his two loving sons.

Dean: Of course, the most troubling question is why do these people assume we're gay?

vs

Sam: It's not food anymore, Dean! It's Darwinism!

Season 2, Round 1, Bracket #3/4:

Dean: When you were little, couldn't have been more than five, you just started asking questions. How come we didn't have a mom? Why did we always have to move around? Where's Dad? I remember I begged you: "Quit asking, Sammy. You don't want to know." I just wanted you to be a kid, just for a little while longer. Always tried to protect you. Keep you safe. Dad didn't even have to tell me. It was just always my responsibility, you know? It's like I had one job. I had one job, and I screwed it up. I blew it, and for that, I'm sorry. I guess that’s what I do. I let down the people I love. You know, I let Dad down, and now I guess I’m just supposed to let you down, too. How can I? How am I supposed to live with that? What am I supposed to do? Sammy? What am I supposed to do?

vs

YED: Not a problem. I know somebody.

Dean: Yeah, you can't kill Death.

vs

Dean: What's dead should stay dead.

Henrickson: You think you’re funny
Dean: I think I’m adorable.

vs

Dean: L.A. A young girl got kidnapped by an evil cult.
Sam: Yeah, and does this girl have a name?
Dean: Katie Holmes
Sam: That's funny... and for you, so bitchy.

Sam: If there's just one part worth saving...
Bobby: Yeah. All right.

vs

Dean: He full-on Obi-Wan'd me!

Season 2, Round 1, Bracket #4/4:

YED: I knew I kept you alive for some reason. Until now, anyway. I couldn't have done it without your pathetic, self-loathing, self-destructive desire to sacrifice yourself for your family.

vs

YED: No, John. You have to sweeten the pot.

Dean: Bitch. Sam: What are you calling me a bitch for?
Dean: You're supposed to say jerk.
Sam: What?

vs

Dean: There's no higher power, there's no God. There's just chaos and violence, random unpredictable evil, that comes outta nowhere, rips you to shreds

Sam: Dean, did you pay attention to History class at all?
Dean: Yeah, shot heard round the world, how a bill becomes a law...
Sam: That's not school. That's School House Rock.

vs

Dean: Don’t worry, Sam - I promise I won't trade you for smokes.

Sam: You're bossy.
Dean: What?
Sam: You're bossy... and short.
Dean: Dude, are you drunk?
Sam: Yeah. So? Stupid.

vs

Dean: What's a P.A.?
Sam: I think it's kinda like a slave.

Already these are hard.

Season 2 Round 1 Bracket 1

I am so proud of you: do I need to explain? I think I do not.

Clowns kill: will never not be funny to me

Quarters: I don't actually remember the other one

Swayze: these are both good ones, I'll go with the triumphant over the scared

Bracket 1:

• I am so proud of you: No contest here. Just none. God, John. Dean.
• He doesn't understand us: He does now, though, doesn't he?
• Enabling your sick habit: He's not well-adjusted, but he is well-fed
• Full-on Swayze!: Trying to peacemake from almost beyond the grave. Go Dean.

Bracket 2:

• I never should have come back, Sam: Always come back, Dean.
• Let me help a little bit: Little brothers can help too!
• I enjoy sunsets: Ah, snarky!Dean
• It's Darwinism!: Hard pick, but this made me laugh harder

Bracket 3:

• I had one job and I screwed it up: Yeah, you did. Then again, you didn't. You did a marvellous job. It wasn't John's son that saved the world, it was Dean's brother.
• What's dead should stay dead: Never, idjit.
• I think I'm adorable: Although the meta of the Katie Holmes quote is very attractive, Dean/Henriksen FTW
• Just one part worth saving: And all the parts he did save! The Lego! The soldier! Your brother!

Bracket 4:

• I kept you alive for one reason: Big mistake, doofus.
• There's no higher power: Ha. Ha.
• I won't trade you for smokes: But maybe rent you out?
• You're bossy...and short: Not short! Still funny.

Quarters: I don't actually remember the other one

It was a comment Dean made at the end of Born Under A Bad Sign referring to the Meg possession. Resulted in bitchface, if memory serves.

Bracket 2:

I never should have come back

We were just starting to be brothers again

My name is Dean Winchester

the most troubling question

Bracket 3

When you were little

What's dead should stay dead

I think I'm adorable

Obi-Wan'd

Bracket 4

I knew I kept you alive for some reason

Bitch...what?

School House Rock

You're bossy

Thanks for the memory jog, ita, I can place it now. Sticking with quarters.

Bracket #1

• Proud of you – aw John I kind of loved you for that and then you had to go and tell him he might have to kill his brother, sigh.
• Clowns kill – it’s all in the delivery…I find myself quoting this line a lot
• I eat – ILU Dean
• Swayze’d mother – hee proud ghost Dean

Bracket #2

• Should’ve stayed dead – breaks my heart –woobie Dean
• Let me help – this was amazingly hard – I picked this one because Sam was trying to lift Dean’s burden
• Aquarius Dean – because you are adorable, it’s true.
• Assume we’re gay – it was the delivery, Jensen has such great delivery. I won’t miss this quote when it goes.

Bracket #3

• What am I supposed to do? – Absolutely heartbreaking. Wordy but OMG every fucking word just guts me
• What’s dead should stay dead – reasonable belief
• Adorable Dean – see Aquarius Dean
• saving the impala/Dean – it’s all in the subtext damn it

Bracket #4

• sacrifice yourself for your family – YED nails Dean to the wall literally and emotionally
• No higher power – again the delivery is fantastic here
• School House Rock – it’s school house rock! And bitchy Sammy
• bossy…short – drunk Sammy!

Season 2, Round 1, Bracket #1/4:

JOHN:You know, when you were a kid, I'd come home from a hunt, and after what I'd seen, I'd be, I'd be wrecked. And you, you'd come up to me and you, you'd put your hand on my shoulder and you'd look me in the eye and you'd... You'd say "It's okay, Dad" Dean, I'm sorry. DEAN:What? JOHN: You shouldn't have had to say that to me, I should have been saying that to you. You know, I put, I put too much on your shoulders, I made you grow up too fast. You took care of Sammy, you took care of me. You did that, and you didn't complain, not once. I just want you to know that I am so proud of you. (A rare nice John moment - also Dean character enlightenment)

Dean: Planes crash! Sam: And apparently clowns kill! (Ah - brotherly love and so very, very funny)

Dean: Did you bring quarters? Sam: Dude, I'm not enabling your sick habit. You're like one of those lab rats that pushes the pleasure button instead of the food button until it dies. Dean: What are you talking about? I eat. (Still funny)

Dean: I full-on Swayze'd that mother! (Because it's excellent)