S3 E16 - No Rest for the Wicked
I lost my night's sleep over this. I mean, c'mon, it's fuckin' Hell. And Dean's in there, hanging from metal hooks that pierce through his skin, screaming for Sammy. And the hanging and torturing went on for 30 years.
Nothing wrong with character torture; stab them, strangle them, make them bleed, make them cry. But sometimes I think that Kripke might enjoy making the guys lives (and afterlives) as shitty as possible a little bit too much.