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I Know What You Did Last Summer
I don't get why this episode is so misunderstood. As I've said before, it's gorgeous. Anyone who said this was the "Saint Ruby" hour wasn't watching the same episode I was. I paid careful attention to Sam and let everything else become background noise. 

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Sam's devastation over Dean's death is groundshaking. He is very, very broken. Jared plays that beautifully! The emotional spectrum that Sam wavers between is literally taller than the man himself. His confrontation with the Crossroads demon shows Sam at his last raw nerve. He's in so much pain he doesn't want to live anymore. The next scene proves it too when he dares Ruby to kill him.
Sam is hurting so bad he without hestiation does the one thing he and Dean never wanted him to do, use his powers. That again kicks in Sam's instinct to spite himself when hope is lost. He couldn't save Dean, he might as well become that monster. The worst thing that could happen is that he dies, the best is that he saves people. He had that mentality about Jess in season one too. He'd rather die in the name of revenge (or justice in his mind) than deal with the pain alone.
So what's a person at the total bottom going to do? Cave into a moment of intense weakness, that's what. When Sam gives into Ruby's advances, he's in deep pain both physically (headaches from demon pulling) and emotionally. He needs something to take that pain away, right or wrong. A brutally desperate man will do the worst possible things, like sleep with a demon.
Ruby had to be there for him. Despite what we like to think. Sam wasn't (and still might not be) in a place to pull things together on his own. He would have destroyed himself. That wouldn't have made a good show.
Criss Angel Is A Douchebag/After School Special
I put these two together for a reason, other than both are Sam centric. I still debate whether they aired in the proper order. I'm wondering if the "You happy Sam?" would have made his decision at the end of Criss Angel all that more powerful. 
In Criss Angel, Ruby decides its button pushing time. Sam needs less time to do cases with Dean and more time with her hunting Lilith. She begs him to do "that" but Sam has a huge problem with "that." Sam's determined to make this his decision though, thus making a great tie back to Metamorphosis. 
He asks Dean if he thinks they're gonna do this when they're old. Dean bluntly tells him they'll be dead (for real) before then. If they do live, they'll become Bobby, who hasn't exactly grown old gracefully. Sam sees the tragic tale of the three aging magicians and even though he doesn't want to do it, he's going with Ruby's plan. "I don't want to be doing this when I'm old," aka, he's ready to sacrfice himself for the greater good.
Of course no sooner than he makes that choice, he gets to revisit a place that gave him one of his few positive experiences in his life. He gets to see again his old teacher, who when he was 14 told him he had choices in life, that he didn't have to go into the family business.  Sam came across as self actualized in this one, even giving that life goes on speech to the ghost of his former classmate, but all that unraveled at the very end. All that confidence, all that pride, fell apart with that one question. That's when he realizes he doesn't have control of his destiny. He is never going to be normal. Remember this, for it comes into play later.
So which ending was better to come first? I could see the answer going both ways. No matter which way, Sam is setting himself up for a fall.
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Sex And Violence
So, just like the doctor that seduces him, is it possible Sam is living like there's no tomorrow? The stakes are getting higher now, and he's gotta step up. He schemes with Ruby behind Dean's back, who's crushed when he figures it out. Then he has the one night stand with the lively doctor, something that's a bit out of character for him (Dean even points that out in the end). Maybe it all means he has nothing to lose?
The siren's spell obviously has the most interesting impact. Spell or not, Dean is pretty hurt by Sam's actions even before they say those awful words to each other. Sam just makes it worse. At the end Sam's mortified by his words and actions in trying to harm Dean, but won't apologize or discuss his sneaking around with Ruby. He uses the siren spell as an excuse to brush everything under the rug. "So, we're cool?" They are so not cool. 


# Lisa 2009-08-13 12:32
I for one loved the progression of Sam's character during season 4 so thank you very much for this very insightful article.
# Cathy 2009-08-13 13:01
I agree, extremely insightful. My heart was broken at the end of When The Levee Breaks, so I was gladdened (look at me, channeling Bobby Singer!) to see Sam expressing remorse. I was dreading that it would be the opposite and that the brother relationship was done for. I'm really looking forward to Dean, in-depth...
# elle2 2009-08-13 15:16

A great read. I love these inn-depth looks at the boys. While it is possible to see elements of this coming as the season progresses it is best to wait until it is all aired and then dive much changes the focus and direction as the pieces slowly but surely fall or slide into place. Sam had a great arc this season and all along throughout the series. Season 5 is going to be fab...all the other have been so I have no doubts.

Great job.
# Ash 2009-08-13 17:54
Among all the lovely articles on your site (and there are many), your character metas are still the most awesome! You basically put everything I *think* into words... and so well too!
# trina 2009-08-14 14:19
While I find Dean to be a very heroic character, I think Sam is one of the more tragic characters that I can remember seeing on TV. Just watching an early season one episode and hearing him talk about his desire to have a normal life kills me. Not only is that not possible now, it never was for him. His fate was written 10 years before he was born.

Also, I loved when Chuck brought up that the demon blood makes him feel more in control. Sam has control issues. Other people's decisions keep making his life a living hell. Of course, now his own decisions have released hell on earth, so what now?
# elle2 2009-08-14 15:20
Trina, I only hope neither brother is a 'true tragic hero' as someone once reminded me that tragic heroes die in the end -- gasp, no!!!!!!

I remember Kripke once referring to Dean as a tragic hero, this on the commentary for WIAWSNB when Dean makes the decision to 'go back' and undo the spell the Djihn had on him. I cringed then at the fear of Dean dying...I think I can let that fear go though for both brothers, at least since Kripke says he's open to another season depending on how well this one fares.

Still, both boys are heroes but you are quite correct, Sam has been forced from the very beginning into this position and that makes him not only very heroic as he struggles to overcome but also deeply sympathetic, despite Season 4 decisions, he's still extremely sympathetic to me.

# Brian 2009-08-15 06:51
I still think we were gypped out of what could have been a really awesome storyline if only they had taken the time to tell it, instead of pushing 90% of it behind a curtain. We only "finally got to know what happens in Sam's mind" in the second to last episode of the season.
# Brian 2009-08-18 01:37
Another view:
Manzanita Crow
# Manzanita Crow 2013-07-11 08:40
I know I'm horribly late to the party since I only started watching SPN this spring. But maybe that means the whole story is fresh in my mind.

I think there is a very important line that hasn't been mentioned. In Criss Angel Jay says "Charlie was like my brother. And now he's dead... because I did 'the right thing.'" I believe that drove Sam towards doing 'the wrong thing' and drinking demon blood again.

Why? Because doing 'the right thing' in the last three seasons resulted in both John and Dean dead and in Hell:
- Sam didn't kill his possessed Dad at the end of Season 1 (I'd say that was the right thing) but it resulted in John dying anyway and going to hell.
- Sam didn't kill Jake at the end of Season 2 (again the right thing) and gets killed. With the result that Dean makes a deal to go to Hell.
- In Season 3 Sam's starting to waver morally, but eventually does 'the right thing' and doesn't listen to Ruby. The result? Dean goes to Hell and Sam goes completely nuts.

Early in Season 4 Sam stops drinking the demon blood because he knows it's wrong. He tries to stop using his psychic powers too, but has to use them on Samhain to save Dean and other people. The powers simply won't go back in the box now.

When his powers aren't powerful enough to stop Alastair at first, and then the demon-killing knife doesn't work, Dean could easily have died. So when Sam hears that line from Jay, it's no wonder he cracks and does 'the wrong thing' by drinking demon blood to increase his powers. He's willing to do anything to save Dean, even go darkside. OK, it's a crazy risk, but Sam's mental health is in tatters already.

I can totally understand why he did what he did. Obviously it was a terrible idea. But it was understandable given his mental state and the Winchester credo of sacrificing yourself for others.

I was pleased when I found this meta cos it goes along the same lines: