|Actor|| Mark Rolston (4.09, 4.10)|
Andrew Wheeler (4.15)
Christopher Heyerdahl (4.15, 4.16, 4.21)
|Dates||????-2009 (killed by Sam Winchester)|
|Episode(s)|| 4.09 I Know What You Did Last Summer|
4.10 Heaven and Hell
4.15 Death Takes a Holiday
4.16 On the Head of a Pin
4.21 When the Levee Breaks
You know... I haven't been up here since Poland '43. Truth is, I loathe it. It's chilly. No stink of blood or sizzle of flesh or the wet flap of flayed skin. I don't know how you stand it.
– Alastair, 4.10 Heaven and Hell
Alastair is a white-eyed demon responsible for torturing human souls in Hell. He is held in high esteem by many of his demon comrades, he is referred to by Ruby as " "Practically the Grand Inquisitor downstairs." He possesses an extensive knowledge and awareness of the universe, having occult knowledge, usage of spells cast in Enochian as well as rituals.
Alastair was initially immune to Sam's psychic abilities, although, ironically, he is eventually killed by them. His durability seems to exceed that of most demons', as Ruby's knife, a weapon that can kill demons, could greatly damage him but could never destroy him.
As a torturer, he is an expert interrogator in that regard, according to Castiel, he had an exceptionally strong will, allowing him to sustain himself while being tortured. Meg was an apprentice of him before his death. He tortured both Dean and John Winchester, and in both instances offered to end the torment if they would become torturers themselves. Alastair reveals that the first seal was broken when Dean accepted this offer.
He also can send an angel back to Heaven by expelling it from its vessel. Alastair has shown to be resistant to an angel's power of exorcism. He possess knowledge of the Four Horsemen of the Apocalypse and has demonstrated power to overwhelm a reaper.
Sam and Dean find Anna Milton hiding in her church. Ruby appears and tells them to run because a powerful demon is approaching. Suddenly signs of the demon's approach break out, including a statue of the virgin Mary weeping blood. Alastair arrives. Sam attempts to exorcise him with his powers, but to no effect. Dean fights with Alastair, who asks if Dean recognizes him.
Alastair: Hello again, Dean. Come on, Dean. Don't you recognize me? Oh,I forgot -- I'm wearing a pediatrician. But we were so close... In Hell.
Sam stabs the demon with Ruby's knife, but he is unharmed. Sam and Dean escape by jumping out the church window.
Alastair appears again to Ruby at a crossroads where she tries to make a deal with him: giving him Anna Milton in exchange for allowing her and the Winchesters to go free. He then makes her a counter offer, capturing and torturing her with her knife. He later has a showdown with Castiel and Uriel in which he overpowers Castiel, but is distracted from harming him by an attack from Dean. The fight is interrupted when Anna reacquires her grace from Uriel, she and Alastair then both disappear in a flash of bright light with Alastair leaving behind only Ruby's knife.
Alastair is attempting to break one of the 66 Seals by killing two reapers 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. Alastair reveals that while his meatsuit was destroyed by Anna, he himself survived. 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 ghostly 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. Later as he confronts Dean, Alastair is captured by Castiel.
Alastair is captured by Castiel and Uriel and imprisoned in a devil's trap, but he refuses to tell them anything about the slain angels. 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.
While withdrawing from the demon blood, Sam hallucinates that he is being tortured by Alastair.
- The name "Alastair" is the anglicized form of the Scottish Alasdair, which is the Scottish (Gaelic) version of Alexander. The latter is the English form of the ancient Greek name Alexandros, which has the meaning "protector of men" in Greek.
- The character may be a reference to British occultist Aleister Crowley, who during his day was dubbed "the wickedest man in the world" by the press. At one point, Led Zeppelin guitarist Jimmy Page developed an interest in Crowley. Page once owned Boleskine House, Crowley's estate on the shores of Loch Ness.
- In addition, another demon named Crowley later appears.
Alastair in Lore
- The character Alastair may be a reference to the demon Alastor in Christian demonology. Alastor is the chief executioner and torturer for the monarch of Hell. He is an exceptionally cruel demon. The name 'Alastor' became a common place term in reference to evil spirits or foul tempered individuals. [source?]