Alastair

Alastair
Seasons	Season 4
Species	Human (Formerly) Demon
Status	Deceased (killed by Sam)
Title/Alias	Hell's Grand Torturer Picasso With A Razor
Occupation	Chief torturer of Hell Lilith's servant
Affiliation	Lilith
Portrayed by	Mark Rolston Andrew Wheeler Christopher Heyerdahl

“	Like roaches, you Celestials. I really wish I knew how to kill you. But all I can do is send you back to Heaven.	”
	— Alastair to Castiel in Heaven and Hell

Alastair (occasionally spelled "Alistair") was a powerful, white-eyed demon who was Hell's grand torturer, and Meg apprenticed under him in the field of torture. He was able to travel from Hell and Earth with incredible ease, something he shares with Azazel. His stature to Lilith is vague, but the way he grudgingly followed her orders indicates that she at the very least out-ranked him. Dean first encountered Alastair in Hell and he is the one in charge of torturing him.

During the 40 years (or 4 months in Earth time) that Dean was in Hell, each day Alastair would ask Dean if he wanted to trade his place for another soul. For 30 years, he refused and, each day, was chopped and killed and then placed back together, only for the cycle to continue. He couldn't bear the pain much longer and, for 10 years, tortured souls. This makes Alastair directly responsible for triggering the Apocalypse.

Personality

Alastair was cruel, even for a demon, especially in his sadism. The more pain he could deliver the happier he was, but not just physical pain--he was also effective in mental torture and stress. He was reasonably patient, criticizing Ruby, stating that young demons were always so impatient and willing to run into things.

As well as enjoying giving pain, Alastair enjoyed taking it, which displayed his masochism. He seemed to enjoy being tortured almost as much as he enjoyed torturing others. However, even he had a threshold for the pain he could withstand. For these reasons, he was the only demon, who didn't just like Hell, but liked it more than Earth, dismissing the Earth as a "craphole" and several times expressing the wish to return down under. He did however obey Lilith, and would never disobey her.

He also held contempt for angels, referring to them as "fanatics" and "pricks", and enjoyed hurting them, even more than he enjoyed humans, souls and demons. He wished he knew how to kill them, rather than simply being able to send them back to Heaven. He was one of the few demons who did not flee in the presence of an angel.

Alastair had a twisted sense of humor, and never missed a chance to exploit something he considered funny or ironic.

Powers and Abilities

Alastair fighting with the angel Castiel.

Alastair was one of the most powerful demons to appear on the show. He casually overpowered hunters, reapers, and likely other lower-level demons. Even in a weakened state from the injuries he sustained from the prolonged torture at Dean's hands, he could still overpower a lower-level angel such as Castiel—an impressive feat, considering the differences in strength between ordinary demons and even lower-level angels. Alastair ranked high in the hierarchy of Hell, although he was still subservient to Lilith. His arrival caused a church statue of the Virgin Mary to weep blood in "I Know What You Did Last Summer".

• Immunity - Alastair could not be killed by Ruby's Knife (though he still found it painful) or smiting from a lower-level angel. He was immune to iron and able to walk on holy ground. Sam's demonic powers initially did not work on him, although Ruby later explained that this was because Sam had stopped drinking Demon Blood; once Sam began drinking blood again, Alastair's powers stopped working on him and Alastair began taking precautions to ensure that Sam would not be use his powers on him, implying that Alastair lost his immunity to Sam's powers (which was later proven true in "On The Head Of A Pin").
• Invulnerability - Alastair withstood would-be fatal injuries such as numerous stabbings and prolonged torture with little reaction.
• Telekinesis - Alastair had the ability to move objects with his mind. He used hand gestures to drag and throw people over large distances without physically touching them. During his first appearance, he also blasted apart a door without noticeable use of gestures.
• Torturing - Alastair was an expert in how to torture humans and demons alike. His skills at torture was such that even other demons feared him, nicknaming him "Picasso with a razor." Because of his prowess, Alastair was often issued special assignments in torture, including breaking John and Dean's souls in Hell and interrogating Anna.
• Teleportation - Alastair could teleport from one place to another, including travel between Hell and Earth. He appeared directly behind Ruby in "Heaven and Hell", despite there having been nobody there even seconds before that. He did the same to Dean in "Death Takes A Holiday" and "On The Head Of A Pin"; in the latter episode, he even slipped out of a number of chains binding him without making them make noise from his escape.
• Immortality - Alastair could potentially live forever. Although his exact age was not revealed, he considered Ruby, who was over seven hundred years old, to be a young demon.
• Knowledge of magic - Alastair knew an exorcism which expelled angels from their vessels; he tried to use this exorcism on Castiel in "Heaven and Hell" and again in "On the Head of a Pin", but was interrupted both times. He also knew Enochian sigils which warded buildings against angels, and a spell which incapacitated reapers. Additionally, he had knowledge of the 66 Seals and how to break them.
• Biokinesis - Alastair directed a psychic attack on Sam and Dean simultaneously in "Heaven and Hell" by raising his hand at them; causing them to grip their chests and fall down, impling that he was attacking their hearts.
• Healing (Possibly)- Alastair may have possessed the power to repair wounds, as Dean described having been repeatedly torn apart and then completely restored under Alastair's charge in Hell.
• Possession - Alastair used a pediatrician as his vessel in "I Know What You Did Last Summer" and "Heaven and Hell". When Anna regained her grace, the light she emitted destroyed the pediatrician, forcing the demon to claim a new vessel when he returned to Earth in "Death Takes a Holiday". He soon fled this vessel and possessed a third man, whom he continued to possess until they were both killed in "On the Head of a Pin".
• Flight - In his disembodied smoke form, Alastair could fly.
• Super stamina - Alastair had an incredibly high pain threshold, withstanding hours of extreme torture from Castiel, Uriel, and later Dean (his own pupil in torturing) without giving up any information. When he got free, he showed no signs of weakness or exhaustion despite multiple injuries to his vessel.
• Super strength - Alastair lifted and strangled Dean with one hand without any signs of strain. He also lifted Castiel and placed him on a hook while they were both in vessels.

Weaknesses

Alastair had very few true weaknesses. He was one of the toughest demons ever to exist.

• Sam Winchester - Although initially immune, he was later surpassed and killed by Sam, after consuming a large amount of demon blood and training further with his psychic abilities. Debatably, Alastair would be weak to other psychic children as well, had they emerged victorious instead of Sam.
• Demon-killing knife - Although immune to the killing affects of knife, it still caused him pain and was temporarily kept at bay when stabbed in a vital area.
• Devil's Traps - Like all demons, Alastair is rendered powerless within a devil's trap. However, his resilience and endurance remain present.
• Higher Demons - Despite being a powerful demon in his own right, he was subservient to demons ranking higher than him. Lilith could easily send Alastair whenever and wherever she wanted.
• Archangels - Only angels of the greatest power could effectively destroy Alastair. Regular soldiers are unable to smite, or even defeat Alastair. Even the projection of Anna's true form merely obliterated his vessel, but did not cause fatal damage to the demon himself.
• Heavenly Host - Multiple Angels acting collectively could capture Alastair in a special unrevealed manner. As highier-tied angels, Seraphs could easily smite him. 
• The Colt - As the Colt could kill all but five things in creation, Alastair could be killed by the Colt as well.
• Death's Scythe - This weapon is capable of killing all beings, even Death itself according to rumors, with ease.
• Holy Water - Although highly resilent to it, it still caused him pain. However, holy water was not enough to stop or seriously bother him.
• Salt - Although resilent to, it still caused him pain.

Biography

Early life

Nothing is known about Alastair's life as a human, nor is it known how he became Hell's Grand Torturer. What is known is that while in Hell, he gained a reputation for being cruel and sadistic - a reputation which made even other demons fear him. He also became one of the few demons who actually enjoyed life in Hell more than life on Earth. At some point in his career, he trained Azazel's "daughter" Meg in the art of torture.

Some time during John Winchester's imprisonment in Hell, Alastair took command in attempting to break him in the name of the first seal; however, John endured for a century before being freed during the events of All Hell Breaks Loose. At the end of No Rest for the Wicked he encountered Dean in Hell, and resumed the same duty as before.

Pre-Season 4

In Hell, Alastair was assigned to torture Dean. He did so for 40 years, he broke him within 30 years. In doing so, the first of the 66 Seals was broken.

Season 4

Alastair in his first vessel.

Alastair resurfaces on Earth to try to capture Anna Milton and use her gift for their gain. During this time, he re-encountered his favorite student Dean who remembered him from Hell. Although his initial attempt was unsuccessful, he manages to get a hold of Ruby's magical knife. Later, he returns and strikes a deal with Ruby, who promises Anna for the safety of the Winchesters and herself. Alastair, after torturing Ruby, accepts. Unknowingly, however, he falls into a trap set by the Winchesters and is confronted by two Angels, Castiel and Uriel. He and his demonic minions get into a fight with the Angels, although his minions are easily killed, Alastair proves to be a stronger opponent, and causally knocks about Castiel, and during the battle, Anna regains her Grace and lets loose of a blast of light that disintegrates Alastair's vessel.

Alastair preparing to kill the Reapers.

He returned a short while later, possessing a new body. He was behind the abduction of a reaper in a small town. He encountered Sam and Dean and fought them, before escaping when Sam revealed that he's immune to his power. He gained a new vessel soon after and abducted a second Reaper named Tessa who Dean knew. He planned to kill the two reapers on the night of the solstice moon to break another of the 66 Seals that needed to break in order to free Lucifer. Sam and Dean, in their astral forms, used their new ghost abilities to fight Alastair; however, he was able to trap them in an iron chain, mocking them about how they often did the same to spirits. However, through a combination of their new abilities, they managed to bring the chandelier down on him, breaking the ring and freeing Tessa. He failed, only being able to kill one reaper, and was captured by the angels.

After seven angels were killed, Castiel recruited Dean to torture information out of Alastair. Alastair simply mocked the fact that his former protégé would be the one to try and break him. Alastair revealed that the first seal was broken when Dean gave in in Hell and began torturing people. This explained why the angels had rescued Dean from Hell. With some help from Uriel, Alastair managed to break free from the Devils Trap he was bound in through water dripping from a pipe and washing away a portion of the symbol.

"You should talk to your plumber about the pipes" -- Alastair to Dean before disfiguring his face with a single punch

Alastair's death.

He quickly beat up Dean and nearly banished Castiel to Heaven until Sam arrived and pinned Alastair against a wall using telekinesis. He tortured Alastair until the demon revealed that the demons were not behind the angel killings. Alastair then challenged Sam to exorcise him, but Sam, now being more advanced with his powers, simply used his abilities to kill Alastair in a similar fashion to what the Colt or Ruby's knife would do. It was later shown that Uriel  was behind the angel killings. He also appears when Sam is hallucinating from his detox of demon blood. In this hallucination, Alastair is torturing Sam.

Appearances

• Season 4
  • I Know What You Did Last Summer
  • Heaven and Hell
  • Death Takes a Holiday
  • On the Head of a Pin
  • When the Levee Breaks (Appears as hallucination)

• Season 6
  • Caged Heat (Mentioned only)
  • The Man Who Would Be King (Mentioned only)

Notes

• Perhaps the reason why creator Eric Kripke decided that Dean should stay in Hell for 40 years is because, in Christianity, the number "40", represents death (Noah's ark being the most famous example).
• The name Alastair might come from the famous occultist Aleister Crowley. Another likely possibility is that it came from the name Alastor, a demon name used in Christian demonology, fitting more with the overall Angels vs Demons theme of Season 4.
• In the entire series, Alastair, Lilith and Ruby were the only demons to have more than two bodies in one season.
• Mark Rolston portrayed Alastair for his first two appearances, Andrew Wheeler for the third, and Christopher Heyerdahl for the next three.
• The way that Alistair speaks, as portrayed by both Rolston and Heyerdahl, seems to be an imitation of Hollywood star Marlon Brando.
• As of yet, Alastair is the only demon shown to not only enjoy hell, but actually prefer it. When Anna took back her grace and became an angel again, he deliberately walked his host into her body so it would be obliterated and he could "return home to his studies". He later laments to the brothers that Lilith planned to keep sending him "back to this arctic craphole" until the angel business was taken care of.
• It seems Alastair's comment about being fond of Dean and his potential may have been true. Once Dean shed the first drop of blood in Hell and broke the seal, Alastair could have thrown him back on the rack for the rest of eternity. Instead he allowed Dean to study under his "tutelage" for ten years, which may have continued forever had the angels not harrowed him from Hell. Admittedly, this might not have been kindness so much as another form of torture. Ruby described Hell as a place where people forget their humanity and become something else—and Dean was certainly becoming something else.
• He is the first of three main antagonists Sam defeats.
• As stated in The Essential Supernatural, Alastair was possibly the second demon ever created.
• Alastair was the fourth demon of the Lore to appear in the show, the first was Azazel, the second was Astaroth and the third was Lilith.
• Alastair implies he had a hand in the creation of the extermination camps in Nazi Germany.