When I asked Sera Gamble at Comic Con last year what more she could possibly do to Sam, especially after what she put him through in "When The Levee Breaks," she answered with delight there was no end to the psychological torture these brothers could go through (and Cas too). After all intense psychological torture wins every time over bloody and painful physical suffering. I think Sera was holding back, for there was plenty of the physical torture. Just look at all the crap each went through.
Had his legs broken and lungs removed by a vindictive angel.
Was captured, tied up, beaten, doused in holy water and was forced to ingest a fair amount of rock salt.
Beaten and force fed demon blood.
Strangled by Mahatma Gandhi.
Got the clap from a vindictive witch.
Got a vicious whack square in the nuts when losing a Japanese game show and was turned into the Impala computer.
Finds out he's the object of one very demented fan girl's affection. I'm sure that made him ill.
Restrained and manhandled after going a wee bit insane.
Is body swapped and subdued by a tranquilizer gun, TWICE.
Is murdered by a vindictive angel.
Goes completely off the deep end in a demon killing spree after caving into the Famine induced overwhelming craving for demon blood.
Is tackled and disgustingly drooled on by a crazed zombie.
Is murdered by vindictive hunters.
Crippled by a set on nasty diseases from Pestilence, including Syphilis. Man, he just can't run from the VD.
Oh, and he becomes the prom suit for Satan himself.
Dean didn't fare too well either:
Beaten up by a vindictive old demon foe.
Suffers from angel induced stage four stomach cancer.
Is pummeled unconscious by his future self. The future self that gets his neck broken by Samifer acting like he was stepping on a cockroach.
Gets wailed on by Paris Hilton and has to deal with Sam rubbing it in.
Gets violently tossed like a rag doll by a vindictive demon.
Has to wear sunglasses at night in a procedural cop show and deliver the Steve Urkel inspired tagline in a bad sitcom. Sure that seems like psychological torture but I'm sure it made him sick to his stomach.
Is devastated emotionally when he has to say goodbye to Jo and Ellen and let them meet their untimely deaths.
Ends up liking body swapped Sam better. (Okay, that's not torture, but what does that say about his relationship with Sam?)
Is taunted by the archangel Michael in one impressive confrontation after getting the crap beat out of him by a vindictive angel.
Is knocked out and captured by Famine only to witness his brother go on an apeshit crazy demon killing spree, thus fracturing his psyche greatly.
Is murdered by vindictive hunters after watching Sam get slaughtered first.
Is captured by his brother and one pissed off angel, earning his own cooling off period in the panic room.
Kidnapped by Gods and...it just gets weird from there.
Also stricken by horrible disease by Pestilence, but he's looking far worse than his brother.
Face and body smashed to an unrecognizable pulp by Lucifer in a Sam suit, then he watches both his brothers fall into the vortex to Hell, essentially left to be the last man standing.
Having said that, none of that wins. The past physical stuff that has won this category before is for pansies compared to these two scenes of extreme psychological torture that capture the prize. It's a tie.
First is Dean's most unnerving ordeal in Chicago, when he's invited for pizza with Death himself in "Two Minutes To Midnight." The intent was to kill, but Dean quickly learns you can't kill Death. Or cheat him either. Or even have a conversation without wetting yourself. Even being forced to have a bite of pizza is enough to make him want to either pass out, toss his cookies, or both. The entire scene is brilliance, with the tension so extreme no one would have guessed that in the end Death was a card carrying member of Team Freewill. He offers a terrified Dean the ring without a fight, but the bargain involves the death of Sam. That makes sense, since death is his thing.
Second, by sake of airdate and not quality, is Sam's mirror showdown with Lucifer in "Swan Song." The great dark one finally has his vessel, but the occupant inside is being feisty. There's only one way to tame that inner beast, through one glorious mind fuck exchanged through a cracked mirror. Sam wasn't the only one rattled to the core.