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Tuesday, November 18, 2025

‘It: Welcome to Derry’ Debuts Midseason Trailer Promising Long-Awaited Return of Pennywise [Watch]

Welcome to Derry
Courtesy of HBO

If you’ve been watching It: Welcome to Derry, you’ve probably noticed that Pennywise has been noticeably absent from the proceedings. The malevolent force known as “It” has, of course, been featured in various forms throughout, but the most famous incarnation has taken a backseat thus far. That’s all about to change. With four episodes currently available and four still to air, HBO has debuted a midseason trailer that teases the return of Pennywise. 

The trailer, which you can scope below, prominently features Bill Skarsgård as the dancing clown. He pops up several times throughout, and you can hear him ominously murmuring to core character Lily (Clara Stack) that he’s always wondered how she’d taste. 

While it hasn’t been officially confirmed exactly which future episodes Pennywise will appear in, it’s very likely that the character will pop up in episode five and recur through episode eight. Episode five is slated to premiere Sunday, November 23rd, with new installments dropping weekly on HBO and Max until the season finale airs on Sunday, December 14th. 

The series, which functions as an origin story for It and It Chapter Two, is planned for a grand total of three seasons. The current season takes place in 1962 and begins with the shocking disappearance of a young boy. Season two will jump back to 1935, and season three will unfold in 1908. 

Jason Fuchs and Brad Caleb Kane serve as showrunners on the series. Andy Muschietti, Barbara Muschietti, and Fuchs developed the series for HBO.

A still from the upcoming HBO Max series It: Welcome to Derry
Courtesy of HBO

How are you liking Welcome to Derry so far? Make sure to let us know in the comments section below.




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