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Come on, you gotta want a little payback for everything I did to you; for all the pokes and prods, hmm? No? How about for all the things I did to your daddy?
~ Alastair taunting Dean while the latter tortures him.

Alastair is a minor-yet-pivotal antagonist of the CW dark fantasy series Supernatural, being a major antagonist in the fourth season. He was Hell's grand torturer who sees torture as an art, having trained another demon and Dean Winchester in the "art". He was responsible for setting the stage for Lucifer's rise and the Apocalypse.

Possessing a pediatrician, he was portrayed by Mark Rolston, who also portrayed Bogs Diamond in The Shawshank Redemption. He was portrayed by Andrew Wheeler in his second vessel and by Christopher Heyerdahl in his third and final vessel.

What Makes Him Pure Evil?

  • Being Hell's grand torturer, he's tortured many souls in horrific ways that mortality would not allow for. One of these torture subjects was a soul that became demonized and would only be known to the Winchesters as Meg Masters. Alastair taught Meg his methods, much like he would Dean centuries later.
  • It's implied that he tortured many innocent concentration camp prisoners in Poland in 1943 during Nazi occupation, when Jews and other "undesirable" races were sent to camps. He may have possessed a doctor or surgeon and performed agonizing experiments on the prisoners, much like other real Nazi doctors.
  • When John Winchester, Sam and Dean's father, is sent to Hell, Alastair takes up torturing him, placing him on a rack and slicing away at him until there's nothing left, only to put him back together at the end of each day, with Alastair offering each time to stop if John starts torturing other souls, but he refuses. This goes on for around a hundred (in Hell's warped time) until John escapes Hell.
  • When Dean is sent to Hell, Alastair does the same thing to him that he did to John: tearing him apart and offering alleviation from the blade if he picked it up himself. Dean breaks after thirty years and tortures souls for his last ten, with Alastair viewing their relationship as that of a teacher and a student. Alastair breaking Dean is significant mainly because:
    1. It broke the first (a righteous man must shed blood in Hell) of the 66 seals needed to break to free Lucifer and allowed for the rest to be broken as well since the first seal needed to be broken before all others, making Alastair the one responsible for kickstarting the Apocalypse.
    2. It forever changed Dean for the worst, making him more violent and sadistic and influencing his behaviors and actions after his resurrection. These traits are made worse when Dean takes on the Mark of Cain, the corrupting influence of which makes him even more sadistic and homicidal.
  • He attempts more than once to capture Anna Milton, a fallen angel-turned-human, to use her ability to hear the voices of angels to the demons' advantage.
  • As Sam and Dean attempt to fight Alastair off, the demon flings Sam down the stairs and fights Dean while reminding him of their time together in Hell. The brothers' injuries from the fight are bad enough to need stitches.
  • Ruby summons Alastair and makes a deal with him, offering him Anna in exchange for letting herself and the Winchesters go. Alastair accepts, but not before kidnapping and torturing her.
    • During this, he reminisces about Hell and how he much prefers it to Earth. Most demons despise Hell and only one other is confirmed to share this sentiment with Alastair.
  • Alastair shows up with two other demons to confront the Winchesters, Castiel, and Uriel and take Anna, engaging them in another fight until Anna regains her angel grace, causing a burst of light which destroys Alastair's vessel.
    • Alastair later comments that his former vessel's wife is still looking for him and that he finds that "hilarious".
  • Meeting with the Winchesters in another vessel at a cemetery, he intends to kill or torture (or both) them, flinging Dean across the graveyard until he flees from a demon-blood-powered Sam.
  • He quickly finds another vessel and continues with his plan to break another seal, kidnapping two reapers for the ritual on the night of the solstice moon.
  • While astral projecting, Sam and Dean arrive at the funeral home where the ritual is being performed but are encircled by and trapped in chains of iron. Alastair enters and shoots the brothers with rock salt, taunting their situation and carrying the ritual out, killing one of the reapers with Death's scythe. He attempts to kill the final reaper, Tessa, but is stopped by a falling chandelier and Tessa escapes with Dean.
  • While the brothers' spirits are still detached from their bodies, Alastair has a demon find and kill their vessels, who fails but kills Pamela, the psychic casting the astral projection spell.
  • The angels capture Alastair and have Dean, as his former protégé, torture him to extract information on a string of angel deaths. Alastair mocks their choosing Dean to be his torturer and laughs at Dean's measly attempts to break him. He also gloats about having tortured John for nearly a century and how much more resilient he was than Dean. Finally, he tells him that as he took the razor to a weeping woman, he broke the first seal, thus the demons have Dean to thank for inadvertently starting the Apocalypse.
  • Thanks to Uriel, Alastair breaks out of his chains and attacks Dean brutally and attempts to kill him and take him back to Hell before Castiel attacks Alastair, who overpowers the angel for a third time and tries sending him back to Heaven, unable to kill him. His last words are spent confessing that the demons aren't behind the serial angel killings, bragging that Lilith would kill hundreds and thousands more angels, and goading Sam, whose hands he is literally at the mercy of, into exorcising him, only to be shocked when Sam kills him.

Trivia

  • Alastair has the least time on screen of any of the Pure Evil villains in the series.
    • He is also the only one to not have been the main antagonist of one of the story arcs.

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See Also
A Song of Ice and Fire Pure Evils | Amblin Entertainment Pure Evils | Arkhamverse Pure Evils | Arrowverse Pure Evils | Batman Pure Evils | Ben 10 Pure Evils | Cartoon Network Pure Evils | Courage the Cowardly Dog Pure Evils | DC Animated Universe Pure Evils | DC Extended Universe Pure Evils | DC Universe Animated Original Movies Pure Evils | Dead by Daylight Pure Evils | Die Hard Pure Evils | Godzilla Pure Evils | Gotham Pure Evils | Hanna-Barbera Pure Evils | Harry Potter Pure Evils | ImageMovers Pure Evils | Justice League Pure Evils | Legendary Entertainment Pure Evils | Middle-earth Pure Evils | New Line Cinema Pure Evils | Roald Dahl Pure Evils | RWBY Pure Evils | Star Wars Pure Evils | Supernatural Pure Evils | Superman Pure Evils | The Conjuring Pure Evils | Teen Titans Pure Evils | Village Roadshow Pictures Pure Evils | Wes Craven Pure Evils | Yu-Gi-Oh! Pure Evils

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God | Lucifer | Lilith | Alastair | Abaddon | Dick Roman | Michael (Apocalypse World)

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