→Winchesters in Hell
[[Dean Winchester]] and [[John Winchester]] both go to Hell after they make agreements with [[demon]]s. Dean bargains with a [[crossroads demon]] to resurrect Sam, and after much debate agrees to go to Hell after one year.<ref name="two22">[[2.22 All Hell Breaks Loose: Part Two]]</ref> [[John]] bargains with [[Azazel]] to resurrect Dean in exchange for [[the Colt]], but Azazel only consents when John's [[soul]] is added to the bargain.<ref name="two01">[[2.01 In My Time of Dying]]</ref>
Dean spends the equivalent of thirty years on [[Alastair]]'s rack in Hell and ten years torturing other souls, roughly 4 months on Earth (40 years in Hell).<ref name="four11">[[4.11 Family Remains]]</ref> John spent almost a century there (10 months in real time).<ref name="four16">[[4.16 On the Head of a Pin]]</ref> Initially, the [[demon]]s intended for John to break under Alastair's torture so that he would become a torturer himself, which would break the first seal. John never gave into the demon's offer,
but Dean eventually does, breaking the first lock on [[Lucifer's Cage]]. Eventually, a group of [[angels]], including [[Castiel]], lay siege to Hell to rescue Dean where Dean's soul is ultimately rescued by Castiel.