Season Two of the television series aired on Castle Rock Hulu from October 23rd, 2019 to December 11th, 2019, for a total of ten episodes. Like season one, stories from this season are inspired by or based on concepts developed by famed horror author Stephen King, by bringing different elements from King's exhaustive oeuvre of work into a single shared continuity. The central focus of this season is a re-imagining of the back-story of Annie Wilkes, who had previously been showcased as the oogie dirty-bird antagonist of King's 1987 novel , as well as the Misery 1990 film adaptation, , by director Misery Rob Reiner. Taking the lead role this season is Lizzy Caplan as Annie Wilkes (or Annie Ingalls as she calls herself) with John Hoogenakker as the mysterious "Tall Man", Tim Robbins as Reginald "Pop" Merrill, Elsie Fisher as Joy Wilkes, Paul Sparks as John "Ace" Merrill, Barkhad Abdi as Abdi Howlwaqdaag, Abby Corrigan as Chance, Matthew Alan as Chris Merrill, and Yusra Warsama as Doctor Nadia Howlwadaag.
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The tagline for this season is "Misery comes to Wednesdays".
Each season of is a self-contained story, though they all take place within the same continuity.
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