Alastair (Supernatural)

Plot

When Dean Winchester is sent to Hell at the end of the third season, the demon Alastair tortures him until Dean agrees to torture other souls himself. Alastair trains Dean as one of his apprentices until the fourth season premiere Lazarus Rising, in which Dean is rescued by the angel Castiel. It is later revealed that while the man Alastair was possessing was vaporized, the demon survived. Alastair debuts in I Know What You Did Last Summer, seeking to capture the fallen angel Anna Milton.

Dean and his brother Sam interfere, but Sam's demonic powers are too weak to harm Alastair. They accidentally stab him with Ruby's demon-killing knife, and Alastair claims the knife as the brothers flee. In Heaven and Hell, Alastair is tricked into a confrontation with the angels Castiel and Uriel after torturing Ruby for Anna's location. Alastair proves more powerful than the angels and gains the upper hand on Castiel, but is seemingly vaporized when Anna is restored to her angelic true form, leaving only the demon-killing knife behind.

Characterization

The original breakdown described Alastair as a calm and composed demon with a placid smile that belies his simmering sadism and evil. Christopher Heyerdahl deemed Alastair's lack of any goodness to be what makes him so much fun, stating that he unabashedly loves creating havoc and pain. The breakdown also called him one of the top demons in Hell and electrifyingly powerful. Nicholas Knight classified Alastair as a demon chief of staff at the top of the hierarchy of Hell, suggesting he might be the second-oldest demon ever created in the show's mythos.

Writer Sera Gamble explained that Alastair, unlike other demons, is exceptionally old and powerful, so he knows a trick or two. Mark Rolston called him the John Gotti of demons. Regarding his relationship with Dean, Rolston found the demon to be a mentor who really took Dean under his wing, wanting Dean to be something great. When Dean was rescued, Alastair felt spurned.

In I Know What You Did Last Summer, Alastair seeks retribution against Dean, hoping Dean might come back into the fold in Heaven and Hell. Although Alastair works with Lilith, Gamble felt he would rather be back in Hell sticking bamboo shoots under fingernails than starting the apocalypse, describing him as a torture artist who is only topside because duty calls.

Development

Rolston had previously auditioned for the series and joked that maybe they were saving him for this role because Alastair was so wicked. The idea that a badass demon could possess an ordinary man helped inspire the voice he developed, which he described as particular, odd, and sometimes wicked, but very believable. He collaborated with the hairdresser to create a weird style that looked normal and bookish. Director J. Miller Tobin gave Rolston free rein over the character in Heaven and Hell but did reel him back on occasion.

Rolston thoroughly enjoyed his time on the series, explaining that actors playing bad guys get to explore the other side of their personalities. He loved the character's big run of juicy dialogue. Gamble revealed that the writers planned for Alastair to reappear after his introduction, stating there was more to come about Dean's time in Hell. Heyerdahl saw Jensen Ackles' humorous performance of Eye of the Tiger and thought working on Supernatural would be enjoyable.

He was asked to audition for Alastair days later. Although he auditioned without seeing Rolston's episodes, his eventual viewing of those fantastic performances made him even more excited. To honor the music that Rolston brought, Heyerdahl developed a three-way between what Mark had done, his own vision, and director Steve Boyum's nuances. Unlike Rolston, Heyerdahl insisted on rolling his eyes for Alastair's transition to fully white eyes, which the visual effects department usually added in post-production, because he thought it was fun.

Reception

Rolston's performance mostly received praise from critics. Diana Steenbergen of IGN called Alastair a formidable new foe and was interested to find out more. Tina Charles of TV Guide saw the character as a force to be reckoned with, hoping Rolston would be around for a while. Steenbergen noted Rolston's perfectly menacing portrayal in Heaven and Hell helped save the episode from being more of a waste, and she was intrigued by his invulnerability and Dean's connection to him.

However, Karla Peterson of The San Diego Union-Tribune was negative toward Rolston's performance in the torture scene with Ruby, observing that he appeared to have been possessed by the ghost of Dinner Theater Marlon Brando, a similarity John Kubicek of BuddyTV also noted. Peterson wrote that Rolston was so awful and amateurish it was distracting. Charles praised Heyerdahl as simply awesome in the role and hated to see him go. Steenbergen agreed that Heyerdahl did an excellent job carrying on what Rolston started, finding him just as menacing and maybe a little creepier, but was ultimately happy to see the character killed off because his voice was fine in short scenes but too over the top with more time.

Peterson disliked Heyerdahl's voice as Alastair, calling his portrayal a bargain-basement Brando. She believed his performance was damaging in the torture scenes of On the Head of a Pin, as they were campy to the point of being laughable, seriously undercutting their dramatic power, and were only salvaged by Ackles' acting. In contrast, Kubicek praised Heyerdahl's casting, describing him as someone who would give Hannibal Lecter the willies, and did not feel the voice detracted from the character's effectiveness.