Normally this is reserved for Sam every year, because face it, the boy has had some really awful things happen to him, but his year, the prize goes to an outsider. Dean electrocuting Cole was pretty damned intense! It was incredible how Dean would deliver shock after shock and Cole just kept asking for more. The boy would wear a dominatrix thin! It’s all that special forces training, which makes him perfect hunter material.
Since we’re mentioning Cole, he did really inflict some harm on poor Sammy, and it wouldn’t be this award without at least mentioning some Sam Winchester misfortune. It made you wince, but Cole definitely learned a few nasty tricks in Darfur. Still, Sam made it pretty easy having a shoulder in a sling when being captured. Just one appropriate press of the thumb in the perfect soft spot and we have the trademark scream of agony!