Please understand that this isn’t about saying which character had a ‘worse’ time in Hell. I just intend to take a closer look at Sam, Dean, Cas and Bobby’s experiences of Hell, and what they could say about that character.
So let’s start with Dean. The facts are these: Dean went to Hell for four months, i.e forty years, after selling his soul, and what they did to him was with the purpose of ‘breaking’ him (in order to break the first seal and yadda yadda).
The most we see of Dean’s Hell involves him stretched out over an abyss, a hook piercing his shoulder. The sexual connotations are there, though never explicitly spoken. With Dean, everything is sexualised- like, practically every monster they meet comes onto him. For instance:
Sex seems to be a kind of safe retreat for Dean, usually. Perhaps this is because only then does he get to be both open and safe- look at his post-coital heart-to-heart with Cassie in Route 666, or Lisa in The Third Man (in hilarious contrast to the following scene, with Soulless Sam working out and casually paying a prostitute).
Monsters pick up on this chink in Dean’s armour, and they always use it against him. All in all, I think it’s a pretty safe assumption that Dean was raped in Hell.
It’s a systematic destruction of all his safe places, basically. And when he gets back, his time in Hell has twisted his perception. He seems to automatically place less trust in Sam when he returns- even before he finds out about the whole demon blood thing- and he seems to have left a part of himself behind, as Alastair says.
Most importantly, though, when Dean’s in Hell he’s screaming for Sam- who told him that he would not go to Hell, that Sam would find a way to save him- and nobody is answering. He has no way of knowing that Sam is tearing himself up trying to get Dean back. And this goes on for forty years.
In short, Hell breaks Dean by making him think his brother has abandoned him, and by using sex- which has always been Dean’s comfort zone- against him. We do see the beginning of a healing process concerning the sex thing, when Dean and Anna have sex in the Impala in Heaven And Hell- it’s a very gentle, peaceful scene, and the way she puts her hand over Castiel’s handprint on Dean’s shoulder is like she’s trying to erase his pain.
Then of course there’s the fact that he turned to torture. It’s interesting that endverse!Dean, who had gone back to torturing for information, only began doing that after he and Sam were separated. Endverse!Dean was frighteningly similar to Dean in Season Four’s On The Head Of A Pin, in fact.
Sam and Dean’s relationship is dangerous, yes. But they need each other anyway. Because otherwise this sort of thing happens.
Sam’s Hell problems were a different animal altogether. Sam jumped into Lucifer’s Cage to save the world, and spent a year and a half down there- about one hundred and eighty years in Hell time. He was basically a source of entertainment of Lucifer, and possibly Michael. There would probably be a revenge element involved too, as it was thanks to Sam that they were in the cage.
When Sam got out and his Hell memories were unleashed, it resulted in a psychotic break.
The question here isn’t so much what happened to Sam in the pit as what didn’t happen to Sam in the pit. Over one hundred and eighty years basically everything would have happened. As Hallucifer says, ‘the rapier wit, the wittier rape’…
Yet the image that is chosen, over and over, to represent Sam’s time in the Cage is this one.
It’s used repeatedly in Season Six. Then, in Season Seven, there’s this:
One day, I will sit down and write an essay entirely about that image. I mean, come on, SYMBOLISM. But not just yet.
The fact remains, they could have chosen anything out of the varied repertoire of things Sam went through, and every single time, they went with fire. Given what he says in Defending Your Life about feeling like being in Hell had erased a lot of his guilt, it seems that Sam’s Hell time was like a kind of trial by fire for him, a purification. One that drives him insane.
And look! He ends up in a mental hospital. Wearing all white. Apart from the Samifer scene in Season Five’s The End, it’s the only time we see a Winchester completely dressed in white. Colour symbolism, yay. Also, I suspect that the Jesus Stubble is no accident.
It’s a genuinely heartbreaking episode, by the way. Basically the culmination and resolution of Sam’s Hell trauma plotline. Sadly, the purification thing doesn’t last long for Sam, as anyone who’s seen the last few episodes of Season Eight- and that awful, devastating I’m not clean speech- will know.
Sam may have felt purified, but Dean certainly hadn’t. Possibly the difference was to do with the reasons that landed them in Hell- whereas Dean was there as a result of what was essentially his own selfishness in resurrecting Sam (though I don’t think any of us blamed him), Sam went in order to save the world. Sam knows he’s made the ultimate sacrifice and that no-one can ask any more of him- until they do, in Season Eight, when he must go through the whole trial-by-fire thing again. Literally, this time.
But the great thing is is that the purification process was never finished in Season Eight. The great thing is is that the Winchesters don’t, when it comes down to it, care about purity. They care about each other.
It comes down to this: Hell reveals their vulnerabilities. Dean’s is through sex and loneliness. Sam is vulnerable because he is convinced of his own invalidity as a person, thanks to the disease he has crawling through his veins. Actually, Sam functions as a pretty solid metaphor for mental illness- that thread’s there right from Season One’s Asylum. Sam’s sanity is as permeable as Dean’s sexuality.
As for Cas, his trip to Hell was brief, simply to discuss his ‘business transanction’ with Crowley. There is no plot-related reason why the Hell shown here would be specific to Cas, but the only time we see this particular variation on Hell is through Cas’s eyes- suggesting some subtextual link to his character.
In case you don’t remember, it’s a line of people stretching way back, and when anyone gets to the front of the queue they just go straight to the back again.
It isn’t difficult to spot a metaphor for the angelic garrison. They, too, are like sheep, waiting for orders from God that never come. Cas’s plotline that season was all about defeating destiny. Obedience is Cas’s Hell. ‘No-one likes waiting.’
In fact, the hilarious picture of Crowley on the wall is suggestive of Raphael’s version of Heaven. Both Raphael and Crowley try to control Cas- as Crowley says, ‘You do realise you are the bottom in this relationship?’ Just as he betrayed Raphael, Cas betrays Crowley.
Obedience, then, is Cas’s Hell. We see this again with Naomi. Like the Winchesters’ relationship, Cas’s rebellious tendencies cause as much harm as they do good. Cas’s entire character is about free will, freedom.
The last one of them to go to Hell was Bobby, whose soul was basically stolen by Crowley- probably for leverage, though we never know for sure. Bobby spent just under a year in Hell, so probably about a century in Hell time.
Bobby went to ‘normal Hell’. Or so we can assume. The episode in which Sam breaks him out- Season Eight’s Taxi Driver- is beautiful, in a Dantesque kind of way.
It seems fitting that the version of Hell that’s implemented at the time Bobby is there is so classical.
It turns out that Bobby’s Hell was endless black-eyed versions of Sam and Dean. Which, I mean, he could just have stuck around for Season Ten, but whatever. I imagine that a hundred years of that kind of psychological screwiness would have a similar effect to Chinese water torture, but Bobby seems to be holding it together relatively okay.
The fact that they chose Sam and Dean to torture him, though- that says a lot. Not Karen, not Jody, not his parents, not Rufus. His surrogate sons. The worst thing Bobby can conceive of is that Sam and Dean would become so twisted and evil. Many people, including Dean himself sometimes, think Sam and Dean are as bad as the things they hunt. It’s a question that acquired special relevancy in Season Ten, with Sam’s involvement in Lester’s deal and Dean’s whole demon thing. Supernatural is in many ways about the grey areas in morality- the road to Hell is paved with, etc etc- but even Team Free Will must draw the line somewhere. Bobby draws it at black eyes. To him, once Sam and Dean become demons, they are no longer Sam and Dean.
Sam doesn’t draw the line here when Dean becomes a demon. He pleads with him instead.
Bobby is vulnerable through Sam and Dean, yes. But by extension he’s vulnerable through the choices they make and what they become. Like Mary saying that the worst thing she can imagine would be for her sons to grow up hunting, the worst thing Bobby can picture is the corruption of his sons.
Thus do Team Free Will’s Hells entwine.