Sam: Dean, what if uh... What if Ruby's right? What if I can take out Lilith?
(Dean looks at him angry over the idea)
Sam: Quit looking at me like that.
Dean: What, are you gonna give her the Carrie-stare and Lilith goes "poof"?
Sam: I don't know what Ruby meant. You know, maybe we should just go ask her.
Dean: Sam, you wanted the knife - I got you the knife.
Sam: Dean, just listen to me for a second. Last time Lilith snapped her fingers and put thirty demons on our ass, and all we got's one little knife? I mean, like you said, we go in smart or we don't go in at all.
Dean: Well, this ain't smart.
Sam: We got one shot at this, Dean. Just one. So if there's a surefire way then maybe we should just talk about it.
Dean: Sam, we are not gonna make the same mistake all over again.
Sam: You said that but what does it even mean?
Dean: Don't you see a pattern here? Dad's deal, my deal, now this? I mean everytime one of us is-is-is up the creek the other is begging to sell their soul. That's all this is, man. Ruby's just jerking your chain down the road. You know what it's paved with and you know where it's going.
Sam: Dean. What do you think is gonna happen? This is me, I can handle it. And if it'll save you...
Dean: Why even risk it?
Sam: Because you're my brother. Because you did the same thing for me.
Dean (scoffs): I know... And look how that turned out. All I'm saying, Sammy, all I'm saying is that you're my weak spot. You are. And I'm yours.
Sam: You don't mean that, we're.. we're family.
Dean: I know. And those evil sons of bitches know it too. I mean, what we'll do for each other, you know, how far we'll go? They're using it against us.
Sam: So what? We just stop looking out for each other?

Dean: No, we stop being martyrs, man. We-we-we stop spreading it for these demons. We take this knife, and we go after Lilith our way. The way dad taught us to. And if we go down, then uh... then we go down swinging.
(Sam just looks at him.)
Dean: What do you think?
Sam: I think you totally should have been jamming "Eye of the Tiger" right there.
Dean: Oh, bite me. I totally rehearsed that speech, too.
Comments
AH! The Trickster, I would have him much higher on my list but as long as he is in there its ok by me!
He obviously has a soft spot for our boys and, even though they are on opposite sides (?), and they tried to kill him (!), AND his methods are truelly his own(!) He was trying to "help" Sam come to terms with the future.
I am sure that by his standards he was doing things the right way...just not very helpful to Sams mind frame.
SOOOO hope we see him "helping" the boys again.
Waiting eagerly to see who is next (any more photos of the non drunks to come?
Diane
The trickster's brilliant but just cos he's funny that doesn't make him well-intentioned. I don't think he was trying to help Sam, he knew the best way to screw him up was to give him a foretaste of his own private hell ... Life without Dean. It wasn't meant to be a tough-love life lesson, it was twisting the knife and then salting the wound for good measure!
That said I do hope he shows up again ... Definitely a class act.
First off, great photos!
I love The Trickster and dearly hope he returns in Season 5. YOu picked a great scene for in this the lesson is taught -- although not learned but hey, what fun would there be then. It's a great time between Jared and Richard. You sum it up so well, this could be a buffoon of a character but excellent casting and fabulous acting make all the difference.
I do find it interesting that he chose to go after Sam in Mystery Spot. I mean, sure, Sam was ripe for the picking (what better way is there to mess with a Winchester than to send another Winchester, ahead of schedule, to do the "hell-fire rumba" downstairs?), but I found it intriguing that the Trickster chose to mess with Sam when it was Dean who actually "killed" the Trickster in Tall Tales.
I guess my take on it was that by messing with Sam, the Trickster was indirectly also messing with Dean since Sam is Dean's weakness (that and pie... bad things always seem to happen when that boy tries to get pie)...but I digress...
Back to the point, the Trickster is Awesome (with a capital 'A') and makes Mystery Spot my all-time (so far) favorite episode. There are a couple of "baddies" that I would rank above him, but I'm extremely curious as to who fills the last 4 spots on your list, Alice!!
I've got the drum roll going for the last 4 baddies!
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