Alastair (Supernatural)

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Supernatural character
Alastair Supernatural.jpg
Mark Rolston as Alastair
First appearance "I Know What You Did Last Summer"
Last appearance "When the Levee Breaks"
Created by Eric Kripke
Portrayed by Mark Rolston
Andrew Wheeler
Christopher Heyerdahl
Species Demon
Gender Male
Abilities Demonic possession
Superhuman strength
Occult knowledge

Alastair is a fictional character on The CW Television Network's drama and horror television series Supernatural, appearing in its fourth season. A particularly infamous torturer in Hell, he is portrayed in succession by actors Mark Rolston, Andrew Wheeler, and Christopher Heyerdahl due to his demonic ability to possess human hosts. The writers created the character to explore series protagonist Dean Winchester's experiences while in Hell, particularly Alastair's tutelage of Dean in torturing other souls. The character received generally favorable reviews from critics, with fans at the time considering him one of the series' best villains.


Described by the character Ruby as "Picasso with a razor", Alastair is a white-eyed demon who tortures souls in Hell.[1] When Dean Winchester is sent to Hell at the end of the third season,[2] he is tortured daily by Alastair, who stops only when he eventually convinces Dean to torture other souls himself.[1] In the fourth season premiere, Dean is rescued from Hell off-screen by angels,[3] who claim to want his assistance in stopping the demon Lilith from breaking the mystical seals on Lucifer's prison.[4]

Alastair debuts on-screen in the episode "I Know What You Did Last Summer", possessing a pediatrician portrayed by Mark Rolston. He seeks to capture Anna Milton, a fallen angel who can hear the conversations of other angels. Dean Winchester and his brother Sam interfere, but Alastair is shown to be highly resistant to Sam's demonic abilities and to Ruby's demon-killing knife. The brothers nevertheless escape with Anna.[5] Alastair is later tricked by the Winchesters into a confrontation with the angels Castiel and Uriel in the episode "Heaven and Hell". He proves to be more powerful, but his host is destroyed in the blast generated by Anna being restored to her angelic true form.[1]

He returns in "Death Takes a Holiday", seeking to kill Reapers to break another seal. He now inhabits a man portrayed by Andrew Wheeler, but a confrontation with Sam forces him to switch to a host portrayed by Christopher Heyerdahl. Though Alastair places sigils preventing angels from interfering, he is stopped by the Winchesters and captured by Castiel.[6] Dean tortures him on Castiel's orders in "On The Head of A Pin" for information about a string of angel murders. Having no knowledge of that, the demon instead reveals that Dean's decision to torture souls in Hell broke the first seal. Uriel, who committed the angel murders because he wants Lucifer freed, later secretly releases Alastair with the hope that he will kill the Winchesters. Alastair incapacitates Dean and begins to exorcise Castiel to Heaven, but is stopped by Sam with his growing demonic abilities. Sam tortures the truth about the demons lack of responsibility in the angel murders and then kills him with his powers rather than exorcise him as Alastair dares him to do.[7]

During "When the Levee Breaks," Sam hallucinates Alastair torturing him among other things.


The original breakdown released to the media described Alastair as a "calm and composed demon with a placid smile that belies his simmering sadism and evil."[8] Actor Christopher Heyerdahl deemed Alastair's lack of any goodness to be "what makes him so much fun", stating, "He just unabashedly loves creating havoc and pain and thinks it's the greatest thing."[9] The breakdown also called him "one of the top demons in Hell" and "electrifyingly powerful".[8] Writer Sera Gamble supported this characterization by explaining that he, unlike other demons who have no experience with angels, is "exceptionally old and powerful, so he knows a trick or two".[10] Likewise, actor Mark Rolston called him the "John Gotti of demons".[11]

Regarding Alastair's relationship with Dean, Rolston found the demon to be a "mentor" who "really took Dean under [his] wing".[11][11] The actor explained, "I wanted him to be something great. When he split, you feel kind of spurned or left out of the loop. Even though I exact a beating on him in my first episode because he did me wrong, in the second one, I'm hoping he might come back into the fold."[12] Gamble noted that this relationship helps reveal the "pertinent details of Dean's Hell story".[13] Although Alastair works with Lilith, Gamble feels he would "rather be back in Hell, sticking bamboo shoots under fingernails", than starting the apocalypse. "He's not a politician. He's a torture artist," Gamble elaborated, "and he'd just as soon stick with what he loves. He's only topside because duty calls."[10]


A man with long hair speaking into a microphone.
Christopher Heyerdahl portrayed the third incarnation of Alastair.

Rolston had previously auditioned for the series, and joked that "maybe they were just saving me for this particular role because [Alastair] was so wicked!". The idea that a "badass demon" could be possessing an ordinary man helped inspire the voice he developed the character around. Rolston described it as "particular, odd, and [sometimes] wicked, but at the same time, very believable".[14] The actor also collaborated with the hairdresser to create a "weird style that looked normal and bookish".[11] Director J. Miller Tobin gave Rolston free rein over the character in "Heaven and Hell", but did "[reel him] back on occasion".[11] Overall, Rolston thoroughly enjoyed his time on the series, explaining, "Actors that play bad guys get to explore the other side of their personalities, things that you wouldn't normally have the opportunity or inclination to do."[15] In particular, he loved the character's "big run of juicy dialogue", which was "quite a bit to sink your teeth into".[15]

Around that time, Heyerdahl viewed actor Jensen Ackles' humorous performance of the song "Eye of the Tiger" that was originally shown in the end-credits of the episode "Yellow Fever". Heyerdahl felt that he would "really love to work on that show [because] that guy looks like a lot of fun", and coincidentally was asked to audition for the role just days later.[16] Although he auditioned without having seen Rolston's episodes, his eventual viewing of those "fantastic" performances "made [him] even more excited" to portray the character.[15] To honor the "music that [Rolston] brought",[16] Heyerdahl developed what he describes as a "a lovely three-way between what Mark had done, my own vision of the character, and the way director Steve Boyum played with the nuances".[15] Unlike Rolston, Heyerdahl insisted that he roll his eyes for Alastair's transition to fully white eyes—the visual effects department usually adds this in during post-production—because he "just thought it was kind of fun".[17]


Rolston's performance received praise from critics, with Diana Steenbergen of IGN calling him a "formidable new foe" in his first appearance.[18][19] She deemed Rolston "perfectly menacing" in the episode "Heaven and Hell", and named his performance as one that helped "save this episode from being more of a waste".[19] Likewise, Tina Charles of TV Guide called him a "a force to be reckoned with", writing, "Here's to hoping Mark Rolston is around for a while."[20] However, Karla Peterson of The San Diego Union-Tribune criticized Rolston's performance in the torture scene of "Heaven and Hell", suggesting that he was "possessed by the ghost of Dinner Theater Marlon Brando". In her opinion, "He is so awful and amateurish, it's distracting."[21]

Charles deemed Heyerdahl "simply awesome" and "hated to see him go".[22] Steenbergen agreed that Heyerdahl did "an excellent job carrying on what Rolston started"—she found him "just as menacing and might even be a little creepier"[23]—but was ultimately happy to see the character die because she found his voice "fine in short scenes, but too over the top the more time that was spent with him".[24] Like with Rolston, Peterson called Heyerdahl's incarnation a "bargain-basement Brando". Heyerdahl's performance in the torture scenes of "On the Head of a Pin" was "campy to the point of being laughable" and "seriously undercut their dramatic power".[25]

In a poll conducted by BuddyTV in 2009, fans voted Alastair as one of the series' top villains.[26] Likewise, readers of The Official Supernatural Magazine voted the character "Best Villain" in an online poll, as well as "Best Demon/Monster/Ghost" in its Readers' Awards.[27]


  1. Cairns, Bryan (June–July 2009). "Hell Breaks Loose". Supernatural Magazine (Titan Magazines) (10). 
  2. Knight, Nicholas (2010). Supernatural: The Official Companion Season 4. Titan Books. ISBN 1-84856-738-3. 
  3. Lloyd, Kate (January–February 2010). "Pit Boss". Supernatural Magazine (Titan Magazines) (14).