Alastair (Supernatural)

''' "You know, it was supposed to be your father. He was supposed to bring it on. But, in the end, it was you. [...] Oh, every night, the same offer, remember? Same as your father. And finally you said, "Sign me up." Oh, the first time you picked up my razor, the first time you sliced into that weeping bitch...that was the first seal. [...] And it is written that the first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break. We had to break the first seal before any others. Only way to get the dominoes to fall, right? Topple the one at the front of the line. When we win, when we bring on the Apocalypse and burn this earth down, we'll owe it all to you, Dean Winchester."

- Revealing Dean's part in freeing Lucifer from Hell, "On the Head of a Pin"

Alastair was a demon appearing on the TV series Supernatural. He served as the tertiary antagonist of the show's fourth season.

He was played by Mark Ralston in his first two appearances, and later by Christopher Heyerdahl in his last three.

Biography
Alastair was once Hell's Grand Torturer. He tortured Dean Winchester every day for thirty years (in Hell time; the Earth equivalent was three months) and repeatedly offered to spare Dean from torture if Dean agreed to torture souls himself. For thirty years, Dean rejected Alastair's offer but eventually broke and took to torturing other souls in Hell, unwittingly breaking the first of the 66 seals keeping Lucifer from escaping.

In "I Know What You Did Last Summer," Alastair is sent by Lilith to capture Anna Milton, a fallen angel reborn as a human with no memories of her life as an angel. He proves to be incredibly strong, and is immune to Sam Winchester's psychic powers as well as Ruby's demon-killing knife. With great effort, the Winchesters and Ruby manage to escape from Alastair.

In the following episode "Heaven and Hell," Anna learns of her true nature and, along with the Winchesters and Ruby, goes to reclaim her grace (the part that made her an angel), but Alastair, Castiel, and Uriel are in hot pursuit. It then turns out that Uriel already has Anna's grace. Alastair then kidnaps Ruby and tortures her until she reveals where the Winchesters and Anna are hiding. Alastair, with Ruby and a couple of demon lackeys in tow, arrives in time to meet the angels, who have also found Anna, and a skirmish breaks out between the two sides. Although his henchmen are quickly killed by the angels, Alastair proves tougher and is able to beat Castiel to the ground. He then tries to send Castiel back to Heaven, but is stopped when Anna recovers her grace from Uriel and creates a blast of energy that destroys Alastair's host.

Alastair resurfaces in "Death Takes a Holiday," trying to break another seal by kidnapping Reapers and killing them on the last night of the harvest. Sam, having grown stronger in his demonic powers, is able to fight back against Alastair, but he flees. Later, after the Winchesters journey to the astral plane, Alastair catches them and mocks them about how they normally do the same thing to ghosts (which they have basically become, only they're still alive); however, they manage to break Tessa, one of the Reapers that Alastair has captured, free with telekinesis, and she in turn frees them. Alastair then confronts Dean, but is ambushed by the angels and imprisoned.

In "On the Head of a Pin," Castiel and Uriel recruit Dean to torture Alastair to get information as to who is killing angels. However, Alastair enjoys the suffering, and he taunts Dean, revealing that he also tortured John Winchester, Dean's father, and that Dean broke the first of the 66 Seals by torturing souls in Hell. He eventually breaks free (secretly helped by Uriel) and proceeds to beat Dean to within an inch of his life, then savagely beats Castiel and prepares to send him back to Heaven but is stopped by Sam, who uses his increased powers to kill the demon.

In "When the Levee Breaks," Sam, while detoxing from demon blood, hallucinates Alastair torturing him in Bobby Singer's panic room.

Quotes
"That tickles. You don't have the juice to take me on, Sam."

- Alastair's first lines to Sam after he tries to use his powers on him, "I Know What You Did Last Summer"

"Come on, Dean. Don't you recognize me? Oh, I forgot -- I'm wearing a pediatrician. But we were so close... in Hell."

- To Dean, "I Know What You Did Last Summer"

"You're gonna have to try a whole lot harder than that, son."

- After Sam stabs him with Ruby's knife, "I Know What You Did Last Summer"

"About how a demon is protecting an angel? We really must revoke your membership."

- To Ruby, "Heaven and Hell"

"You know...I'd always heard that you were a devious, cowardly little slut. You don't disappoint."

- To Ruby, "Heaven and Hell"

"You know the problem with your generation? Instant gratification. It's all "now, now, now." No patience, no craftsmanship. But I do have to say...this knife of yours...it's an exquisite piece. You must tell me where you found it. 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. So, the sooner you cooperate, the sooner I can finish up with this ghastly angel business and return home to my studies. But no rush. Let's take our time...relish the moment. Now, I'm going to remove this, but don't you go smoking out of that meat. You won't get very far."

- Torturing Ruby, "Heaven and Hell"

"Don't you touch a hair on that poor girl's head!"

- Suddenly appearing behind the Winchesters, Anna, Castiel, and Uriel, "Heaven and Hell"

"Name-calling. That hurt my feelings...you sanctimonious, fanatical prick."

- To Uriel after he insults him, "Heaven and Hell"

"Sure. Just give us the girl. We'll make sure she gets punished good and proper."

- To Castiel, "Heaven and Hell"

"Sorry, kiddo. Why don't you go run to Daddy?"

- To Castiel after he tries to exorcise him, "Heaven and Hell"

"Dean, Dean, Dean... I am so disappointed. You had such promise."

- To Dean after he attacks him with a crowbar, "Heaven and Hell"

"Nah. Just the pediatrician I was riding. His wife's still looking for him. It's hilarious."

- To the Winchesters, "Death Takes a Holiday"

"No time to chat. Got a hot date with death."

- To the Winchesters, "Death Takes a Holiday"

"You're stronger, Sam. You've been solo-flexing with your little slut?"

- To Sam after his powers have no effect on Sam, "Death Takes a Holiday"

"Boys. Find the place okay?"

- To the Winchesters after they're captured, "Death Takes a Holiday"

"Rock salt's not so much fun anymore, is it?"

- After shooting a ghostly Dean with rock salt, "Death Takes a Holiday"

"Well, go on. Why don't you try some of your mojo on me now, hotshot? It's hard to get it up when you're not wearing your meat, huh?"

- Taunting Sam, "Death Takes a Holiday"

"Ah, if only I could. But they just keep sending me back up to this arctic crap-hole."

- After being told to "go to Hell," "Death Takes a Holiday"

"No, to kill death twice. It takes two to break a seal. I figured another one would show up, though. They're like lemmings."

- To Dean, "Death Takes a Holiday"

"An old friend lent it to me. You know, he doesn't really ride a pale horse? But he does have three amigos. And they're just jonesing for the Apocalypse!"

- Brandishing Death's scythe, "Death Takes a Holiday"

"It pays to have friends in low places."

- "Death Takes a Holiday"

"You can't run, Dean. Not from me. I'm inside that angsty little noggin of yours."

- Cornering Dean in an alley before being captured, "Death Takes a Holiday"

"I'm sorry. This is a very serious, very emotional situation for you. I shouldn't laugh, it's just that—I mean, are they serious? They sent you to torture me?"

- To Dean, "On the Head of a Pin"

"Or what? You'll work me over? But then, maybe you don't want to. Maybe you're, ah, scared to."

- To Dean, "On the Head of a Pin"

"Not entirely. You left part of yourself back in the Pit. Let's see if we can get the two of you back together again, shall we?"

- To Dean, "On the Head of a Pin"

"You have not disappointed me so far. Come on. You gotta want a little payback for everything I did to you. For all the pokes and prods. Hm? No? Um...how about for all the things I did to your daddy?"

- To Dean, "On the Head of a Pin"

"I had your pop on my rack for close to a century. [...] John Winchester--made a good name for himself. A hundred years. After each session, I'd make him the same offer I made you: I'd put down my blade if he picked one up. [...] But he said "Nein" each and every time. Oh, damned if I couldn't break him. Pulled out all the stops, but John, he was, well, made of something unique. The stuff of heroes. And then came Dean. Dean Winchester. I thought I was up against it again. But daddy's little girl, he broke. He broke in thirty. Oh, just not the man your daddy wanted you to be, huh, Dean?"

- Taunting Dean, "On the Head of a Pin"

"Holy water? Come on. Grasshopper, you're gonna have to get creative to impress me."

- To Dean, "On the Head of a Pin"

"Go directly to Hell. Do not pass go, do not collect two hundred dollars."

- To Dean after he starts torturing him, "On the Head of a Pin"

"There's that little pig-poker. I wondered where it went."

- After Dean brandishes Ruby's knife, "On the Head of a Pin"

"Do you really think this is gonna fix you? Give you closure? That is sad. That's really sad. Sad, sad."

- To Dean, "On the Head of a Pin"

"I carved you into a new animal, Dean. There is no going back."

- To Dean, "On the Head of a Pin"

"Now it's your professionalism that I respect."

- To Dean, "On the Head of a Pin"

"You're just not getting deep enough. Well, you lack the resources. Reality is just, I don't know, too concrete up here. Honestly, Dean...you have no idea how bad it really was, and what you really did for us. [...] The whole bloody thing, Dean. The reason Lilith wanted you there in the first place."

- To Dean, "On the Head of a Pin"

"Something caught in my throat. I think it's my throat."

- To Dean, "On the Head of a Pin"

"Believe me, son, I wouldn't lie about this. It's kind of a religious sort of thing with me."

- To Dean, "On the Head of a Pin"

"You should talk to your plumber about the pipes."

- Before attacking Dean after getting free, "On the Head of a Pin"

"You got a lot to learn, boy. So I'll see you back in class, bright and early, Monday morning!"

- Beating Dean, "On the Head of a Pin"

"Well, almost. Looks like God is on my side today."

- After Castiel stabs him with Ruby's knife to no effect, "On the Head of a Pin"

"Well, like roaches, you celestials. Now, I really wish I knew how to kill you. But all I can do is send you back to Heaven."

- To Castiel, "On the Head of a Pin"

"Stupid pet tricks."

- After Sam stops him from killing Castiel using his demon powers, "On the Head of a Pin"

"Lilith is not behind this. She wouldn't kill seven angels. Oh, she'd kill a hundred, a thousand."

- To Sam, "On the Head of a Pin"

"Oh, go ahead. Send me back, if you can."

- Alastair's last words, "On the Head of a Pin"

"Hello, Sam. It's a pleasure to see you again. Looks like I have you all to myself here. Goodness. How will we pass the time?"

- Appearing to Sam as a hallucination, "When the Levee Breaks"

"So polite all of a sudden. Very nice. I appreciate that."

- To a begging Sam, "When the Levee Breaks"