→4.10 Heaven and Hell
===[[4.10 Heaven and Hell]]===
[[File:Alistair with Death's weapon.Jpg|300px|thumb|right|Alastair in his new [[meatsuit]], preparing to break one of [[the 66 Seals]].]]
[[Ruby]] tells [[Sam]] that Alastair is "practically the Grand Inquisitor" in [[Hell]] and that she more scared of him than even [[angels]]. She suggests that he resume drinking [[demon blood]] so that he can exorcise Alastair, but Sam refuses. Later on, Ruby fulfills her part in Sam's plan by letting Alastair find her. Alastair derides her for protecting Anna, an [[angel]], when she is a [[demon]], and rejects her offer to trade him Anna for the safety of herself, Sam, and [[Dean]], instead capturing her and torturing her with [[Ruby's knife|her own knife]] to force her to tell him where Anna is. While torturing her, Alastair reveals that he actually vastly prefers Hell to Earth (which he loathes), having only left it because he must deal with "this nasty angel business." Eventually, Ruby leads him and his minions to Anna; she is unwilling to simply tell him what he wants to know because she knows that he would just kill her afterwards. Alastair and his minions find that [[Castiel]] and [[Uriel]] are also at the site and are about to execute Anna. Dismissing Castiel's warnings that they will be killed if they do not leave, the [[demon]]s fight the angels to stop them from killing Anna. Although Alastair's minions are quickly killed by Uriel, Alastair proves too powerful for Castiel to smite and overpowers the angel. When Dean hits him over the head with a crowbar, Alastair shifts his attentions to him and Sam and launches a [[Telekinesis|telekinetic]] attack on their internal organs while chastising Dean about his lost "potential." He tries to intervene when he sees Anna regain her [[grace]], but gets vaporized instead, leaving behind only Ruby's knife. Later, Dean tearfully reveals to Sam that after every day of torture in Hell, Alastair would offer to stop if Dean agreed to torture other souls; although Dean initially refused, he eventually gave in because he couldn't take it anymore.
===[[4.15 Death Takes a Holiday]]===