Apple TV+’s ‘The Off Weeks’ Builds Star-Studded Cast: Annaleigh Ashford Joins Ben Stiller and Jessica Chastain in New Limited Series

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Apple TV+ is ramping up its lineup of premium limited series with fresh casting announcements for The Off Weeks, the eight-episode thriller starring and executive produced by Ben Stiller and Jessica Chastain.

The project, which has been generating buzz since its greenlight in September 2025, continues to attract top talent as it moves through pre-production.

On January 16, 2026, Deadline exclusively reported that Annaleigh Ashford (Tony Award winner for Kinky Boots, recent standout in Happy Face on Paramount+ and Impeachment: American Crime Story) has been cast as a series regular.

She’ll play Jade, the next-door neighbor to Stiller’s character, Gus Adler. Ashford brings her signature blend of charm, depth, and Broadway-honed versatility to the role, following her Emmy-nominated turn in Welcome to Chippendales and acclaimed stage work in revivals like Sweeney Todd opposite Josh Groban.

This announcement follows closely on the heels of another key addition: Arian Moayed (Emmy-nominated for Succession as Stewy Hosseini, seen recently in Nobody Wants This Season 2 and Guy Ritchie’s Fountain of Youth) joined as a series regular on January 14-15, 2026.

Moayed will portray Angelo, Gus Adler’s boss. The casting reunites him with Chastain, his co-star from the 2023 Broadway revival of A Doll’s House at the Hudson Theatre, adding layers of proven chemistry to the ensemble.

From showrunner and executive producer Alissa Nutting (Made for Love) and directed by Michael Showalter (The Idea of You, The Dropout), The Off Weeks centers on Gus Adler (Stiller), a writing professor whose life unravels after a divorce.

He barely keeps it together during his “on weeks” with custody of his kids, but his “off weeks” take a dangerous turn when he falls intensely for the enigmatic Stella West (Chastain). Her mysterious arrival creates a high-stakes clash between his parental responsibilities and personal desires, blending thriller tension with emotional complexity.

The series is produced for Apple TV+ by global independent studio wiip, in association with Apple Studios. Executive producers include Nutting, Stiller (via Red Hour, with John Lesher), Chastain (via Freckle Films, with Kelly Carmichael), Showalter, and others like Jordana Mollick (Semi-Formal Productions) and Dean Bakopoulos.

With no filming start date or premiere window confirmed yet, the project remains in the casting and pre-production phase—meaning more exciting additions could be on the way.

Stiller’s ongoing Apple collaboration (following the Emmy-winning Severance) and Chastain’s upcoming Apple thriller The Savant make this a natural fit for the streamer’s high-quality originals slate.

Fans of character-driven dramas, sharp writing, and powerhouse performances have plenty to look forward to. As the cast solidifies, The Off Weeks is shaping up as one of Apple TV+’s most intriguing upcoming limited series.