CASTLE ROCK Boss on Annie’s ‘Demons,’ Ties to Season 1, and What Might Come Next

[Warning: This post contains spoilers for the season 2 finale of CASTLE ROCK.]

As CASTLE ROCK ended its second season, Annie Wilkes (Lizzy Caplan) was able to escape the cursed town…at a price.

Though Annie was able to help take down the Marsten house—thanks to Pop’s (Tim Robbins) foresight to drug himself before his murder, so he was able to help Abdi (Barkhad Abdi) and Nadia (Yusra Warsama) blow the place up from the inside—Joy’s (Elsie Fisher) time with the beings unnerved her mother/sister. When Joy started lying, Annie was convinced her daughter was possessed…and drowned her.

Unfortunately for Annie, she discovered a letter from Joy, expressing her regret over misleading her, but expressing a desire to get away for a bit—and Annie was horrified to realize she had killed her daughter.

Though it initially seemed like Annie was able to revive Joy, and the duo were able to get their happily ever after in the Laughing Place, Annie’s visit to a reading of her new favorite author, Paul Sheldon, revealed that Annie was now hallucinating her still-dead daughter.

CASTLE ROCK showrunner Dustin Thomason breaks down the heartbreaking ending, the bigger ties to season 1, and much more…

The ending felt very full-circle: the season started with a young Annie being on the cusp of drowning Joy to now actually, accidentally, going through with it. But given Annie had to get to a place where MISERY could plausibly happen, I imagine there were a number of other options the writers’ room had before landing on this. How did you ultimately end up with the ending that was chosen?
When you start to tell a story about Annie Wilkes, and you start to think about, well, what is what is the character of Annie Wilkes? That was something that I spent a lot of time with the writers sort of trying to imagine and get to the heart of.

What we came to was this notion, and I believe that Stephen had this in mind, as well, that she is not just a super fan, but somebody who is fatally obsessive. Somebody who has held a grip on the things that she loves too tightly, until she squeezes the life out of them. And so we wanted to make that metaphor literal, in a way.

You can imagine writing MISERY-inspired season of CASTLE ROCK where she was obsessed with some composer or artist. But it felt, to us, the more interesting choice was what does the broader obsession mean? And how can that be related to a person? And so, when we began, the idea was always that Joy, whose name is the opposite of misery, would would eventually be replaced by Misery.

As you say, Joy couldn’t outlive the season. And the question of Annie’s struggles with her mental state, and the demons inside of her, it felt like the final act of it had to come out in the form of loving and trying to control and obsessing over the thing that she loves most.

As you point out with the river question, the water motif, that came a little later, but it was all sort of linked together. Her mother tried to drown her, she tried to drown the baby in the water, the first song is “Let the River Run.” That motif has been building all season long. And so it felt sort of inevitable that it needed to end in a in a river or lake and that it was going to end in a in a place that felt like it could be the utopia we know that she’ll never achieve.

Just to clarify, at what point is it when Annie kind of breaks and imagines a better life? Is the letter real and the inability to revive Joy is when she snaps, or does it happen when she actually kills Joy?
I think that the letter is real. Basically, she realizes that she has done this thing and harmed the thing that she loves most in the world. She has lost her grip on reality to an extent that she has, and that forces her to think about a life and integrate Joy—just as she has, kind of more painfully over the course of the season, integrated her mother and father into her daily life. So she’s integrated the ghost and memory of Joy into her daily life.

The season ends with Annie at a reading of Paul Sheldon’s—who is at the center of the MISERY story with Annie—but we never see his face. Was there ever any discussion about trying to cast someone in that role? Or did you want to just kind of leave it focused on Annie—and the reveal that Joy was in her mind—in that moment?
We had a lot of conversations about it, as you can imagine. We actually had a very, very serious and significant actor playing him. But we never filmed his face, because, to me…it needed to be Annie’s story. And as soon as you showed Paul, it suddenly became Paul’s story. If we had suddenly showed you James Caan [who portrayed Paul in the film] there, then it suddenly becomes James Caan’s story. And it was really important to me and to Lizzie and all the writers that we made sure that MISERY was the next chapter, not the end of this chapter. Joy is the end of this chapter; we wanted to give Annie and Joy’s emotional questions the center stage.

I had a moment when we saw Paul’s body where I wondered, “Are they going to have a digitally de-aged James Caan? Or will it be one of his sons?”
The James Caan IRISHMAN trick! [Laughs.]

In terms of who you did cast as Paul, can you say if it was someone who’s already been in the CASTLE ROCK world or was it an entirely new person?
It’s a new person. And who knows, maybe we’ll see that person again.

In addition to the season being about Annie’s backstory, ‘SALEM’S LOT played a big role. What was the balance in trying to also close out that chapter in the finale? Was there ever a version where we checked back in with Castle Rock post-Annie leaving to see how the town was after the Marsten house was destroyed?
You never know who might pop up again come a later season, as we proven. Episode 9, to me, was sort of the culmination of the emotional side of the story of Pop and Nadia and Abdi. There’s some great, we hope, twists and turns in the first half of this [episode]. It was always in our mind that this final half [of the episode] would be this dread-filled journey back to where we started. We started in this strange, tiny world of Annie and Joy in the first five minutes of the season, and that we would come back to that singular relationship and focus on it for not just the final few moments, but really the sort of final statement of the show for the season.

‘SALEM’S LOT is a fairly dense story, and I imagine, if you wanted, you could have done an entire season around that. In bringing it to Annie’s story, what were the discussions within the room, and potentially with Hulu and Stephen, about not going full-on vampires?
When you look at this ending and you think about sort of the the guiding metaphor of a teenager becoming someone else…adolescence and vampirism [could be] linked as well. But I think that what felt interesting to me was building a story where ultimately Annie wouldn’t be able to tell whether Joy was really the Joy that she knew and loved, or the Joy that had been taken over by some other being. That was sort of a guiding principle in a way in terms of the magic and the mythology of the season. Because, ultimately, the sort of metaphor of an adolescent turning into someone else felt really, really interesting and really like something that Annie wouldn’t be able to stomach.

And the truth is that ‘SALEM’S LOT, when you look at the book and the short stories, vampires are not the only baddies. ‘SALEM’S LOTt has been hit by by mayhem and murder things before. So it felt like instead of diving directly into the lore of the book, why not use it as kind of a springboard and have our own kind of vampires, if you will?

To look at the larger, series-wide mythology, the finale also confirmed a bit more about The Kid (Bill Skarsgård) and how he’s connected to these stories and Castle Rock Lake’s overall purpose. Is Bill now the linchpin to the series, where you will bring him in every season to explain how everything fits into Castle Rock as a whole?
Well, I will always try, in every project, to get Bill to come in for a few days. [Laughs.] He’s great and I do think this season suggests that he is the or a linchpin of the overarching mythology. And so, without making any promises, I can tell you that that Bill returning certainly is very much in my mind.

There was also a missing poster in the finale for Henry Deaver (Andre Holland). We’ve had other tidbits throughout the season tying things into the characters we met in season 1, including the fact that The Kid was held in Shawshank, Dale’s letters, etc. So are these a different universe’s version of these characters or is the Henry we watched in season 1 now missing?
Well, I think that there are a lot of signposts along the way; I tried to not be heavy-handed with them, but I would hope it would imply that we were dipping in the universe that we were in in season 1.

There was a lot of ambiguity in season 1. The question of whether The Kid’s story was even true becomes very central to the reveals of this season. I think that, ultimately, what we’ve learned this season is that there are other dimensions and other other heres, other nows, as they say. But the question of what exists in those other heres and now, whether they are a parallel universe that looks just like this Castle Rock or the wild west of the gunslinger universe is yet to be seen.

But just to clarify, we saw another timeline/universe last season, when The Kid was telling the story of where he came from, correct?
We saw The Kid describing to Molly that universe. Now one starts to wonder whether the details of that story, in a season that was very much about storytelling, were to be believed, given that he appears to be some sort of interdimensional God or demon.

Last season ended with a mid-credits tag that hinted at Jackie (Jane Levy) going to The Overlook. This season, there wasn’t one. Was that move done so people didn’t misinterpret where the show might go in season 3?
To be clear, nobody told me we couldn’t play with last season’s tag. One of the things that I love so much about MINDHUNTER was the way that they put those little teasers into every episode, and the story wasn’t paid off until later.

I find there be something, I hope, rewarding about patience. [Joking.] Jane Levy, if you’re listening let’s talk. [Seriously.] We plant seeds, and and then the flowers grow; you just don’t maybe know exactly when they’re going to grow. So I hope that that’s actually a pleasure for constant viewers if they continue to watch the show and sort of, “Wow, I didn’t know that that was going to sort of bump up against that piece of the story again.” And there are reasons and a map for why we’re doing some of these things this way. But the funny thing is that there was so much—and I understand why—reaction last season to the idea that we were obviously going right to The Overlook. And I was smiling to myself a little bit during that period, because I knew that it was going to have to be a longer term relationship if people wanted to see that.

And just as a part of the larger King universe, it might have been difficult to do a SHINING-influenced season when DOCTOR SLEEP was in theaters.
And, to be honest, Castle Rock as the town is really, really important to the connective tissue of what the show is, I think. It felt important to me not to depart from Castle Rock too quickly…with the understanding that I certainly know that the show can and will go to those more far-flung places eventually.

CASTLE ROCK: Sam Shaw and Dustin Thomason on Getting the Tone Right in a Stephen King Adaptation

At this point, is there anything you can tease about a potential third season?
I can tell you that the soft anthology that is CASTLE ROCK will continue and the mythology will continue to grow. But I do think that there’s a real opportunity to explore far flung places in connection that still have a grounding to the town.

Do you anticipate bringing in an iconic character like Annie and centering it around them, or would you go back to season 1 where it was mostly original characters, with a few King characters in supporting roles?
If Lizzie will ever come back, I will have her. I feel like we told Annie’s story in this show and we know where that story goes next.

But I feel like part of the exciting proposition of this [series] is the anthology format and being able to embrace and to rub elbows with some of these great King characters. And there are so many of them; the truth is there is an embarrassment of riches. And so it’s about trying to narrow it down to what is the right story to tell for each season.

I think both [ways] are interesting in different ways. And, on a writing level, they’re certainly challenging in different ways. The challenge of writing characters that are supposed to exist in the King canon that don’t is that your baseline, your bar, is the master. That’s a great challenge, but a fun one. And then the challenge of taking canonical characters and adapting them is also significant, because you feel like you want to do justice to the world and the character that he created and so many people love.

That was certainly one of the hardest challenges with Annie. There’s no question that I was nervous taking on Annie, and I hope we did Stephen and Annie justice in a way that would be rewarding to fans and to people who also haven’t seen the movie or read the book.

What would you like to see in a third season of CASTLE ROCK?

RELATED:

• CASTLE ROCK Boss on Crafting ‘The Laughing Place’—and Its Twists
• CASTLE ROCK: Paul Sparks on the Very Memorable Season Premiere Scene
• CASTLE ROCK Post-Mortem: Dustin Thomason on That Supernatural Twist
• CASTLE ROCK Team Teases Bringing (New) MISERY Into Season 2
• CASTLE ROCK Season 2 Trailer: Lizzy Caplan’s Annie Wilkes Goes to Drastic Measures
• CASTLE ROCK: Lizzy Caplan, Elsie Fisher, Tim Robbins, Garrett Hedlund, and More Join MISERY-Inspired Season 2
• CASTLE ROCK Season 1 Finale: Dustin Thomason on That Mysterious Smile, Timelines, and Season 2
• Did CASTLE ROCK’s Finale Tease the Season 2 Theme?
• CASTLE ROCK: Sam Shaw and Dustin Thomason on Getting the Tone Right in a Stephen King Adaptation
• CASTLE ROCK: Bill Skarsgård on Diving Back into the Stephen King Universe

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