Castle Rock Season 2: The Return of Annie Wilkes

Annie Wilkes is making her terrifying return in Castle Rock season 2. It’s been a longtime coming for one of Stephen King‘s most beloved villains, who until now has only existed through the point of view of her victim, Paul Sheldon. In the book and in the brilliant movie starring Kathy Bates, Annie is an obsessive stalker bent on torturing her favorite novelist until he gives her what she wants: a new beginning for his most famous character, Misery. The story is shocking, gruesome, and a deft examination of fandom taken too far (and it still works as a scathing commentary on the toxic fandom that pervades the internet today).

But Castle Rock season 2 isn’t rehashing that story. The second season picks up earlier in Annie’s life. She’s on the road, running from a mysterious past that may not be what you expect. When she gets stuck in Castle Rock through unforeseen circumstances, Annie’s life is changed forever, and a new wave of violence washes through the cursed town.

In the role of this younger Annie is Lizzy Caplan (Masters of Sex), who completely transforms for a portrayal that lands somewhere between Bates’ legendary turn and something wholly original. As we said in our spoiler-free review of the first episode, Caplan is at her very best as the neurotic Annie, exposing a different side of the character that will surprisingly make you sympathize with her. Watching her nervously shuffle from scene to “cockadoodie” scene, it seems that no one else could have played this role but Caplan. 

The actor wasn’t so sure about taking the role at first, though.

“My knee-jerk reaction was, ‘This is totally terrifying. Nobody could touch [Bates’] performance. I love it so much. Who do I think I am to even attempt to do this?’ And usually when I feel that way it means I have to do it. Because it’s a scary, daunting proposition.”

Caplan, who is a big fan of the book and movie, understands the weight of the role and worried about doing the character justice, but she found comfort in the fact that Castle Rock wasn’t treading familiar territory. 

“Luckily, our story, we see our Annie in so many different scenarios that it’s not an exact carbon copy, but I’m hoping that they can eventually, in the future, be seen as companion pieces or at least will be the bratty little sister to the epic masterpiece that is the Misery movie.”

You can tell from speaking to her that Caplan has a real love for the character, especially when it comes to the different sides of Annie’s personality. She sees a softer, tragic side to Annie that informed her portrayal.

“One of the things that I love the most about the film, even more so than the book, is that yes she’s the villain of that story but there are so many sides to her. And what makes her so menacing and unpredictable, terrifying is that there really is a warm softness to her as well as a super aggro maniac version. And she vacillates between the two of those.”

Caplan “watched clips of [Bates’ perfomance] regularly” during the “very, very long stretch in rural Massachusetts.” Filming for Castle Rock season 2 took a grueling seven months, according to the actor, so there was a lot of time to study. Caplan had wrapped only a week before we spoke. 

Despite taking on the role, Caplan has yet to meet her predecessor, whose influence is still felt across all of King lore. If the novel didn’t solidify Annie’s position as a top-tier King villain, Bates’ untouchable performance absolutely did. 

“I have not spoken to Kathy Bates about the role at all. I would love to. I fantasize about the occurring the future if all goes well,” Caplan says. “If all doesn’t go well then I will just hide from her if I ever see her out anywhere. But apparently she’s very lovely.”

Whether Caplan sticks the landing or not, one thing is for sure: her take on the character will be welcome by fans hoping to learn more about Annie’s life before Paul Sheldon, the typewriter, and the cabin. And for the first time, Annie’s life is being told through her own perspective. We see her pain, her fears, and the goodness she’s trying to hold on to despite her demons. There’s a real sense that Annie is reclaiming her narrative in Castle Rock.

“I don’t think you could make a long form show like this, a long form story like this, without at least trying to give her enough of a story that makes you feel anything other then purely afraid of this person. Because even when I watch the film I’m not purely afraid of her…She does all this stuff, but she also saves [Paul’s] life.”

Caplan teases that Annie’s youth, which is told in flashbacks throughout the season, is a key to understanding this other side of the character. 

“We want Annie to be a full three dimensional human being. So we delve deeply into her backstory, her childhood, why she is the way she is. But also in our show she is very much out and about in the world, interacting with other people, while in the film and the book she’s already very isolated and alienated.”

Even if Annie were to turn out to be the hero of this particular story, Caplan suggests that the end result might tragically still be the same. This winding road may still lead to Misery and Paul Sheldon. There are even hints of this inevitability in the first episode, as we watch Annie listening attentively to a Misery audiobook.

“Enough shit happens in Castle Rock that you believe that she would want to get a house in the middle of nowhere and not speak to anybody.” 

Mr. Sheldon should be worried.

Castle Rock season 2 premieres on Wednesday exclusively on Hulu. 

John Saavedra is an associate editor at Den of Geek. Read more of his work here. Follow him on Twitter @johnsjr9.