Actor(s): Mark Rolston, Christopher Heyerdahl
Appearances (In chronological order):"I Know What You Did Last Summer"
"Heaven and Hell"
"Death Takes a Holiday"
"On The Head Of A Pin"
"When the Levee Breaks" (Sam's Hallucination)
Species: Upper level, white-eyed demon.
Powers/Strengths: . Standard Demon super-strength, durability, and ability to possess humans. Especially gifted in torture, Alistair's job in hell is to 'break' people. Superior against Sam's abilities, and resistant to Ruby's demon-killing knife.
"I'll see you in class, bright and early, Monday morning."
We are first introduced to Alistair in "I Know What You Did Last Summer" (4x9). He busts in with his creepy smile, totally intent on capturing the red-headed Angel-Radio, Anna, for himself.
He vanishes when Anna is restored to her angelic state, only to return in Death Takes A Holiday, snatching up Reapers to break more seals, and wearing a brand new people-suit. He draws the attention of Sam and Dean, who draw the attention of our favored Angel, Castiel, who brings the smack down on his demon-ass.
In 'On A Head Of A Pin' the student masters the teacher and we see without seeing, Alistair beneath Deans blade on the orders of Castiel. He proves to much for Dean, as often the teacher does, and refuses to break, though he does brag loudly just how much Dean delighted him in Hell.
Escaping his Devils Trap with the surprising help of Uriel, he goes for the kill on Dean and Castiel, and this time it's our beloved little Boy King who puts the kibosh on his plans. Sam steps in, full of fury and demon-blood power, demanding that Alistair tell him who is behind the angel-murders.
With his gift, Sam tortures him in ways Dean never could, only to learn that Alistair knew nothing all along. He kills him without flinching, but it isn't the last time Sam will see Alistair. No, he reappears in "When The Levee Breaks" as a hallucination, and the torture lives on.
Alistair is probably best known for his affiliation with our Dear Dean. Rarely have we seen an oogie-boogie who could get beneath Dean's skin. Alistair, having actually been under his skin at the tip of a blade, seems to be the exception. He preys of Deans weaknesses and makes him doubt, a dangerous thing when they are fighting a war of faith. Alistairs words linger with Dean, long after the demon is gone. We can only hope one day Dean will know just how evil he is not.