‘It: Welcome to Derry’ Season 2 gets a major update as showrunner teases new Pennywise

Season 2 of the HBO Stephen King prequel jumps back to 1935 and a gang of bank robbers
A still from ‘It: Welcome to Derry’ (Cover Image Source: Prime Video)
A still from ‘It: Welcome to Derry’ (Cover Image Source: Prime Video)

Showrunner Brad Caleb Kane has shared that ‘It: Welcome to Derry’ Season 2 will feature the Pennywise monster in a previously unseen variation, and shared with Deadline that Bill Skarsgård is “a different kind of Pennywise.” Kane also remarked that the upcoming chapter is “a bigger season” than the first one, and likened its atmosphere to a “Warner Bros. gangster movie,” featuring “bank robbers and Hoovervilles and street urchins riding the rails religious fundamentalism.” He was promoting his ‘Friday the 13th’ prequel series, which dropped on Peacock October 15.

A still from ‘It: Welcome to Derry’ (Image Source: Hotstar)

Scripts for the season are reportedly about halfway written, and a production schedule has already been established. Director Andy Muschietti is in the midst of hiring new characters, and HBO has yet to formally announce its Season 2 cast. The new setting certainly contributes to the change, as ‘It: Welcome to Derry’ Season 2 will take place in 1935, in the middle of the Great Depression. The story follows the Bradley Gang, a gang of bank robbers who stop in Derry to reload their arsenal, only to encounter something far more terrifying. HBO officially announced the renewal in August 2026, with Kane promoted as sole showrunner after sharing production duties with Jason Fuchs on Season 1. Andy and Barbara Muschietti retain executive producer positions via their Double Dream production banner, alongside Kane, Roy Lee, Dan Lin, Jamie Travis, and Dhana Gilbert. 

Season 1 was set in 1962, and each subsequent chapter will leap back another 27 years, corresponding to the interval between Pennywise appearances in Stephen King’s novel. Viewers have already caught a glimpse of this era, as the Season 1 opening credits show the Bradley Gang massacre with the burning Black Spot and Kitchener Iron Works explosion. The gang members, whose decaying bodies were exhumed by the US Air Force in Operation Precept, featured in the second episode of the first season. In the book, the gang echoes the real Brady Gang, whose members were gunned down in Bangor, Maine.

A still from ‘It: Welcome to Derry’ (Image Source: Hotstar)

Skarsgård previously portrayed the infamous clown in ‘It’ (2017) and ‘It Chapter Two’ (2019), before donning the makeup for the first time in six years for ‘It: Welcome to Derry’ Season 1. The actor also depicted another denizen of Derry, Bob Gray, a human carnival performer who initially gave the Pennywise the Dancing Clown his name in 1908. Skarsgård is also one of the show’s executive producers. The eight-episode first season launched October 26, 2025, starring Jovan Adepo, Taylor Paige, James Remar, and Madeleine Stowe in a star-studded ensemble. Notably, the season’s finale was the first to depict that Pennywise experiences time differently from humans, even though the clown was killed in ‘It Chapter Two.’ Kane also revealed to the New York Post that the upcoming season will feature ”new kids, new characters, maybe some old characters.” The production is set to begin in Summer 2027.

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