I watched the first season of Castle Rock back when it aired, a lifetime ago in 2018. Outside of the truly stellar seventh episode “The Queen,” I felt pretty medium on the show. It was a cool idea with a great cast but so incredibly slow moving and often felt like they were constantly winking at Stephen King super fans — like an inside joke I was missing out on, as a more casual King fan myself.
I spent a lot of time at the end of 2025 compiling my year end lists, so come Jan. 1, 2026, I felt like I had nothing new to watch. I randomly came across Castle Rock as a suggested watch on Hulu — I’d heard the show’s second season was better than the first and I love Lizzy Caplan. The display image for the series had her bloodied and brandishing an axe, so sure why the hell not. I turned the show on.
I enjoyed the season for what it was, but wouldn’t say I loved it exactly. The plot has a slow burn background supernatural story that seems to have nothing to do with Annie until it does, when it fully becomes her problem in the last few episodes. It brings back only two characters from the first season, in quick cameos, yet it takes place in the same town and time period as the first season. It underutilizes Barkhad Abdi and Yusra Warsama who had a great brother/sistser dynamic — and overall I’m still not even sure of a lot of the whats and whys of the season.
But you know what I did love? Lizzy Caplan as Misery’s Annie Wilkes. I was unclear if this was Annie pre-Misery or just an alternate universe version of her until the very end (spoiler: she was a pre-Misery Annie). But my god was she truly phenomenal.
Lizzy Caplan had some big Oscar-Winner-Kathy-Bates sized shoes to fill—but she made the shoes into her own. She avoided doing Kathy Bates drag and somehow made the character feel familiar yet new. We knew this was a woman who was mentally ill and dangerous even before we saw her do on-screen murders, yet this story of Annie was a new one. She creates such an unease with her pitch perfect performance and constant, unblinking wide-eyed stare and peculiar cadence. It’s almost a shame her Annie was wasted on the final season of a Stephen King show that wouldn’t be talked about enough.
It’s weird to say, but I found myself rooting for Annie. I wanted her fate to be different than her fate in Misery. Caplan brought a lot of heart to the role—she seemed to genuinely love her daughter, Joy (Elsie Fisher), and just want some semblance of a regular life that could never ever happen. She self-medicated, she murdered, and she had quite a few breakdowns all while trying to be a good parent, something she was most definitely not. Her fits of rage often lead to murder — but she also was almost murdered by her mother as a kid and then later, as a teen, murdered her own father, albeit kinda-sorta accidentally so ... ya know, cycle of trauma blah blah.
We eventually even learn that Joy is not her daughter but her step-sister, whom she kidnapped after murdering their parents, and eventually had genuine love for. Joy, as a baby, laughed as Annie was about to do a murder-suicide, and it gave Annie a change of heart. It made her feel love — both from and for the baby. It’s an oddly touching flashback moment considering everyone involved in the scene is covered in blood and fleeing a murder scene. I’d often forget Annie was a murderer, even with the shows countless brutal reminders, and just want things to work out for her.
Castle Rock’s second season also gave Annie her hero moment—she was one of the few in the town not to be possessed by the spirits of a long-dead cult that worshipped Bill Skarsgård’s Not-Pennywise-But-Maybe-Pennywise-But-Also-Maybe-The-Devil character (another underutilized actor, cast just to confuse the audience since the first of the new It movies had just come out). Every plot point is wildly convoluted and I couldn’t even tell you why she wasn’t possessed. But we do get Annie Wilkes brandishing a pistol and fighting alongside the remaining townsfolk with free will to help save her daughter and take down a town possessed by a long dead cult—or whatever. She also stabs someone in the eyes with syringes during a fit of rage, so there’s that. Even typing that out, I realize it reads like fan fic, but like, so what who cares?
In the end, Annie and Joy make it out of the town of Castle Rock fairly unscathed. But only for Annie’s psychosis to take over and make her think her daughter did indeed get possessed — so she, of course, drowns her. It’s heartbreaking — made even worse by the fake out of her saving her daughter with mouth-to-mouth, which we quickly learn was a delusion. The season ends on a sad note with Annie fully delusional, thinking Joy survived her drowning and is next to her at Paul Sheldon’s book signing.
We know where that cockadoodie story goes.
With that being said, there’s a new, way more popular Stephen King mashup show that just ended its debut season—It: Welcome to Derry. The town of Derry is name dropped in Castle Rock and both shows mention the Shawshank Redemption’s titular prison, so like, why not throw Caplan’s Annie Wilkes in there? We ended Season 1 on a flash forward cliffhanger. It wouldn’t even need to carry-over from Castle Rock. it could be a new Annie that’s just also played by Caplan in the same way she played her previously. Not unlike how the Tom Holland Spider-Man movies cast J.K. Simmons as J. Jonah Jameson once again, after having played that same character years earlier in the Tobey Maguire Spider-Man movies.
I’d love to see Annie encounter Pennywise — or even just existing in this weird supernatural town where she’s the biggest non-supernatural threat. Would Pennywise get a kick out of her? Would he eat her? Would she protect the children from him or feed them to him? Would the deadlights have no effect on her because she’s already insane?
Who knows! But I’d love to find out. Caplan’s Annie was just so well-done and dynamic, she deserves to be seen again. And maybe this time around, we get Caplan an award for her incredible performance.
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