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Sam and Dean go undercover to investigate a string of murders at their old high school. The case causes them to flashback to their time there recalling how Sam was picked on by the school bully while Dean was Mr. Popular.
A mysterious death draws Sam and Dean to a town full of old-school magicians. Their investigation leads them to Charlie, Jay and Vernon, three friends who were famous magicians in their day but have now been replaced by flashier, younger magicians. One of them has made a deal to acquire real magical powers, but the price was extremely high. Sam and Dean must figure out a way to reverse the spell before others are harmed.
Sam and Dean enter a small town in Iowa, where three men have inexplicably beaten their wives to death. The guys realize that behind the murders is a Siren, a creature that can take different forms and desperately needs love and compels people to destroy themselves as a show of devotion. The Siren eventually puts Sam and Dean under their spell and pits the two brothers against each other in a fight to the death.
After spending four long, horrific months in Hell, Dean Winchester is miraculously raised from the Underworld and resurrected by an angel of the Lord God Himself named Castiel, one of several angels who appears throughout the season. After Dean reunites with his father-figure friend Bobby and his brother Sam, the rest of the season follows the brothers, with the help of their friend Bobby, as they work with Castiel and his subordinate and friend Uriel to stop Lilith's plan of breaking the 66 Seals, which would allow the fallen archangel Lucifer himself, AKA Satan or The Devil (who was once the favored angel of God but rebelled against Heaven for not serving humans and therefore was cast down), to be released from his cage in Hell.