|actor= [http://www.imdb.com/name/nm0001679/ Mark Rolston] ([[4.09 I Know What You Did Last Summer|4.09]] & [[4.10 Heaven and Hell|4.10]])<br>[http://www.imdb.com/name/nm0923766/ Andrew Wheeler] ([[4.15 Death Takes a Holiday|4.15]])<br>[http://www.imdb.com/name/nm0382216/ Christopher Heyerdahl] ([[4.15 Death Takes a Holiday|4.15]], [[4.16 On the Head of a Pin|4.16]] & [[4.21 When the Levee Breaks|4.21]])
- 2009 (killed by [[Sam Winchester]])
|episodes= [[4.09 I Know What You Did Last Summer]]<br>[[4.10 Heaven and Hell]]<br>[[4.15 Death Takes a Holiday]]<br>[[4.16 On the Head of a Pin]]<br>[[4.21 When the Levee Breaks]] (hallucination)
|text= I know you
want to fuck my father, but my dads down in my asshole.
|source= [[4.10 Heaven and Hell]]
is a [[Demonology|white-eyed demon]] whose past is largely unknown but is implied to be quite long. When he was created is unclear, but he considers the centuries-old [[Ruby]] to be "young" when compared to himself.<ref name="four10">[[4.10 Heaven and Hell]]</ref> He also claims to be an "old friend" of [[Death]]'s,<ref name="four15">[[4.15 Death Takes a Holiday]]</ref> who had been imprisoned since Biblical times.<ref name="five10">[[5.10 Abandon All Hope...]]</ref> Alastair is present for World War II, at which time he is involved with the concentration camps in Poland. He returns to [[Hell]] after 1943 and does not resurface on Earth again until 2008, as he prefers to spend his time in Hell, torturing [[souls]], only heading topside when it is absolutely necessary.<ref name="four10" /> Alastair takes [[Meg]] as his apprentice and trains her at some point prior to his demise in 2009.<ref name="six10">[[6.10 Caged Heat]]</ref>.
is charged with breaking the first of [[the 66 Seals]] by forcing " The Righteous Man" to torture other [[soul]]s in Hell. He first attempts to break this seal by torturing [[John Winchester]]'s soul from 2006 to 2007, promising to stop only if John agrees to torture other souls. However, John continually refuses the offer and eventually escapes Alastair's clutches through the [[Devil's Gate in Wyoming |Devil's Gate]].<ref name="four16">[[4.16 On the Head of a Pin]]</ref><ref name="two22">[[2.22 All Hell Breaks Loose: Part Two]]</ref> A year later, Alastair receives John's son [[Dean Winchester |Dean]] from [[Lilith ]] as a replacement for John.<ref name="four16" /> Although Alastair expects similar resistance from Dean that he got from John, he succeeds in getting Dean to agree to the offer in a third of the time John resisted it. Once Dean breaks the first seal, this allows the rest of the seals to be broken.<ref name="four16" /> Impressed by Dean's potential, Alastair keeps training him as an apprentice until [[ angel]] s rescue Dean.<ref name="four09">[[4.09 I Know What You Did Last Summer]]</ref > Alastair is sent to Earth to capture and interrogate [[Anna Milton]] on what she hears other angels saying. However, he fails due to the combined efforts of [[Sam]], Dean, Ruby, and Anna herself.<ref name="four10" /> He is sent back up to Earth once again to participate in breaking more seals. His attempt to sacrifice two [[reapers]] during the winter solstice is thwarted by Sam, Dean, and [[Castiel]],<ref name="four15" /> the last of whom captures Alastair to interrogate him on who has been killing members of his [[angel garrison]].<ref name="four16" /> Alastair proves too strong-willed for the angels to break and they call Dean in to torture his old tormentor, but to no avail. Alastair only gives up the information when Sam tortures him with his [[demon blood]]-enhanced powers; after Alastair reveals that he only knows that no demons are behind the murders, he becomes the first demon killed by Sam's growing powers.<ref name="four16" />
[[File:AlastairKnife416.jpg|thumb|350px|Alastair survives being stabbed with [[Ruby's knife]].]]
Alastair has white eyes (including pupils and irises).<ref name="four09" />
He is noted as an expert interrogator and torturer,<ref name="four10" /> and is also incredibly resilient to being tortured himself; according to [[Castiel]], he has an exceptionally strong will, allowing him to withstand extended torture from both [[angels]] and one of his own apprentices.<ref name="four16" /> Alastair possesses an extensive knowledge of the occult as well as [[Enochian]] spells and rituals, including an incantation with an unknown negative effect on [[angel]]s<ref name="four10" /> as well as another incantation that expels an angel from his [[vessel]] and sends him back to [[Heaven]],<ref name="four16" /> and spell-work to incapacitate [[reapers]].<ref name="four15" /> His presence causes statues to weep blood.<ref name=" four09" />
===Powers and abilities===
Telekinesis|Telekinetic]] <ref name="four09" />* Can [[Possession |possess]] humans.<ref name="four09" />* Has high resistance to [[ Ruby's knife]].<ref name="four09" /> * [[Teleportation]]<ref name="four10" />* Unaffected by the smiting powers of [[ angel]] s.<ref name="four10" />* Can overpower [[angels]],<ref name="four10" /> though he does not possess the power to kill them.<ref name=" four16" /> * Superhuman durability.<ref name=" four10" /><ref name=" four16" /> * The power to telekinetically inflict damage onto humans's hearts with a gesture.<ref name=" four10" /> * Superhuman strength.<ref name="four16" />
Can be killed by [[ Sam]]'s powers if Sam has recently consumed [[ demon blood]]. <ref name="four10" /><ref name="four16" />* Is unable to perceive an [[ angel]] 's true form without his [[meatsuit]] getting obliterated in the process.<ref name=" four10" />* Is vulnerable to [[ devil's trap]] s, [[ holy water]] , and [[ salt]].<ref name="four16" />
===[[4.09 I Know What You Did Last Summer]]===
Alastair leaves [[Hell]] and [[Possession|possesses]] a pediatrician to capture and interrogate [[Anna]]. He follows [[Sam]] and [[Dean]] from Anna's house to
the church Anna is hiding at. [[Ruby]] tries to get Sam, Dean, and Anna to leave as quickly as possible to avoid Alastair, but realizes that it is too late when signs of his approach break out, including a statue of the virgin Mary weeping blood. Although she convinces Sam to exorcise Alastair with his powers, they have little effect on Alastair, who uses [[telekinesis]] to fling Sam down the staircase before attacking and overpowering Dean. He taunts Dean about their "closeness" in Hell, prompting Dean to finally recognize Alastair, even in his [[meatsuit]]. Sam returns to stab Alastair with [[Ruby's knife]], but much to the Winchesters' horror, the [[demon]] does not die. As Alastair pulls the knife out, Sam and Dean flee from him by jumping out the church window and he allows them to escape so that he can use them to lead him to Anna again.
===[[4.10 Heaven and Hell]]===
[[Ruby ]] tells [[Sam]] that Alastair is "practically the Grand Inquisitor" in [[Hell]] and that she is more scared of him than even [[angels]]. She suggests that Sam resume drinking her [[Demon blood|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 hearts while chastising Dean about his lost "potential." He tries to intervene when he sees Anna regain her [[grace]], only to get 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 held out for the first thirty years (three months on Earth), he eventually gave in because he couldn't take it anymore and spent the last ten years of his time there (one month on Earth) torturing other souls under Alastair's instruction. [[File:Alistair with Death's weapon.Jpg|350px|thumb|left|Alastair in his new [[meatsuit]], preparing to break one of [[the 66 Seals]].]]
===[[4.15 Death Takes a Holiday]]===
Now in a new [[ meatsuit]] (his previous one having been destroyed by [[ Anna]] ), Alastair is attempting to break one of [[the 66 Seals]] by killing two [[reaper]]s under a solstice moon. He confronts [[Dean]] and [[Sam]] in a cemetery, and injures Dean, but Sam is resistant to his powers and fights back, revealing that he survived his last encounter with Anna. He flees when Sam tries to [[exorcise]] him with his powers and later returns in yet another meatsuit. When the boys become non-corporeal, and therefore subject to [[ghost]]ly weaknesses, they track Alastair down at a funeral home and he traps them with an iron chain. He kills one [[reaper]], but the boys rescue [[Tessa]] , preventing the seal from being broken. Later as he confronts Dean, Alastair is captured by [[Castiel ]].
===[[4.16 On the Head of a Pin]]===
[[File:AlastairKilled.jpg|thumb|right|350px|Alastair is killed by [[Sam]].]]
Alastair is captured by [[Castiel ]] and [[Uriel]] and imprisoned in a [[devil's trap]], but he refuses to tell them anything about the slain [[angel]]s. [[Dean]] is recruited as an interrogator because he was formerly Alastair's student during his time in [[Hell]]. After extensive torture, Alastair breaks free Uriel having sabotaged the devil's trap to prevent his role in the angelic deaths being revealed. He almost kills Dean, but is stopped by Castiel, who throws [[Ruby's knife]] and embeds it in Alastair's chest. Alastair pulls the knife out and fights Castiel. He manages to trap him against a pillar, and admits that while he is unable to kill the [[angel ]], he will send him back to [[Heaven]]. Alastair begins to chant, but he is stopped by Sam, who has become strong enough to overpower him with ease. Sam forces Alastair to talk, then kills him via his abilities.
===[[4.18 The Monster at the End of This Book]]===
[[Dean ]] reveals that [[Castiel ]] has told him about [[Sam ]] torturing and killing Alastair with ease. Dean thinks that this is one of the signs that Sam is going dark -side.
===[[4.20 The Rapture]]===
[[Dean ]] points out that [[Sam ]]'s powers used to be strong enough to kill Alastair but are now not even strong enough to kill a low-level [[demon ]].
===[[4.21 When the Levee Breaks]]===
While undergoing forced withdrawal from
[[demon blood ]], [[Sam ]] has several hallucinations, the first of which is Alastair inexplicably returning. Sam hallucinates that he is strapped down and tortured by Alastair with a knife , but eventually Alastair disappears and Sam realizes that he is hallucinating.
===[[4.22 Lucifer Rising]]===
[[Ruby ]] reveals that not even Alastair had known that she was working undercover for [[Lucifer]] and [[Lilith ]].
===[[6.10 Caged Heat]]===
To prove that she is capable of making [[Crowley]] give into her demands, [[Meg]] reveals that she had apprenticed under Alastair in [[Hell]] like [[Dean]] had, and Dean grudgingly concedes that this means she can make Crowley do whatever she wants
. Meg doesn't reveal when she undertook this apprenticeship, but it must have been before Alastair's capture in [[4.15 Death Takes a Holiday]], as he was killed in [[4.16 On the Head of a Pin|the following episode]].
===[[6.20 The Man Who Would Be King]]===
[[Crowley ]] mentions Alastair when listing off those who underestimated the threat the Winchesters pose and paid the price for it .
==Alastair in Lore==