Alastair

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Name	Alastair
Actor	Mark Rolston (4.09, 4.10) Christopher Heyerdahl (4.15, 4.16, 4.21)
Dates	Unknown - 2009
Location	Deceased; Alastair was killed by Sam Winchester
Occupation	White Eyed Demon and Grand Torturer of Hell
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

Alastair was played by Mark Rolston for two episodes, and Christopher Heyerdahl for three.

• Alastair is referred to as "The Grand Inquisitor Downstairs"
• Alastair was a white-eyed demon
• He was highly resilient to Ruby's Knife
• Dean as well as John encountered Alastair in Hell
• He was originally immune to Sam's powers
• Alastair can send angels back to heaven
• Alastair's True Demonic form was witnessed by Dean while he was in Hell
• Alastair has displayed great amounts of Demonic strength and resistance; even after his First Meatsuit was destroyed by Anna's angelic blast when she retrieved her grace, apparently it didn't kill him, instead, his meatsuit was ultimately affected by the blast. ^{4.15 Death Takes A Holiday}
• Alastair on many occasions, proved to be very unsuccessful when conducting rituals. In these three Episodes the following rituals were preformed:

4.10 Heaven And Hell- It was in this episode that Alastair first conducted a ritual. Alastair first conducted a ritual, that apparently, would allow him to send Cas back too the realms of Heaven.

4.15 Death Takes A Holiday- In this particular episode Alastair preformed a ritual that allowed him to kill Reapers.

4.16 On The Head Of A Pin- In this episode Alastair attempted once again to send Cass back to Heaven, apparently Alastair was aware that he wasn't able to kill angels, he even stated this, in which he said "I really wish I knew how to kill you, but all I can do is send you back to Heaven."

• Both of his attempts to Send Cas back to Heaven were unsuccessful.

4.09 I Know What You Did Last Summer

Alastair is pursuing Anna Milton and attacks Sam and Dean, while Ruby takes Anna to safety. He appears to be unaffected by Sam's powers and is able to mercilessly beat the brothers, while also appearing to be able to withstand being stabbed in the heart with Ruby's Knife. Sam and Dean escape him, although they suspect he let them go in case they could lead him to Anna. Alastair was played by Mark Rolston in this episode.

4.10 Heaven And Hell

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 and captures and tortures her with her knife. He later has a showdown with Castiel and Uriel in which he seems to almost nearly kill Castiel. Anna then reacquires her Grace from Uriel, she and Alastair then both disappear in a flash of bright light. Alastair was played by Mark Rolston in this episode.

4.15 Death Takes A Holiday

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. When the boys become non-corporeal and track him down in a funeral home, he traps them with an iron chain. He kills one reaper, but the boys rescue Tessa. Later as he confronts Dean he is captured by the angels, led by Castiel. Alastair was played by Christopher Heyerdahl in this episode.

4.16 On The Head Of A Pin

Alastair being tortured by Dean.

Alastair is captured by Castiel and Uriel, but he refuses to tell them anything about the slain angels. Dean is recruited as an interrogator, because he was formely Alastair's student during his time in Hell. After extensive torture Alastair breaks free and almost kills Dean, but is stopped by Castiel, who is soon overpowered by Alastair. Before Alastair can send Castiel back to heaven, he is stopped by Sam, who has become strong enough to overpower him easily. Sam forces Alastair to talk, then kills him via his abilities. Alastair was played by Christopher Heyerdahl in this episode.

4.21 When The Levee Breaks

While withdrawing from the Demon Blood, Sam hallucinates that he is tortured by Alastair. Alastair was played by Christopher Heyerdahl in this episode.

Alastair trivia

• 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?]
• 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.

Links

• Interview with Mark Rolston who plays Alastair