Get ready to head back to Derry.
Six years after the last time Pennywise appeared on-screen in the film It Chapter Two (2019), the dancing clown is returning in the new series IT: Welcome to Derry.
The fresh cast for the HBO Max show includes Taylour Paige, Jovan Adepo, Blake Cameron James, Chris Chalk, James Remar, Stephen Rider, Madeleine Stowe and Rudy Mancuso, with Bill Skarsgård reprising the role of Pennywise.
Set 27 years before the events of It (2017), the series is set to explore a new side of Pennywise, Skarsgård said.
“It was fun,” the actor told Happy Sad Confused podcast host Josh Horowitz in December 2024. “I enjoyed it more than I thought I would, actually, and there’s parts of it where we got to explore sides of old Pennywise that we haven’t seen. And that’s fun.”
Ready to watch the films and new prequel series? Here’s everything you need to know about how to watch the It movies in order.
It: Welcome to Derry (2025)
Courtesy of HBO
The new series will be set in Derry in 1962, 27 years before the first film takes place.
Andy Muschietti, who directed the original films and is a co-developer of the new series, told a crowd during New York Comic Con in October 2025, as reported by The Hollywood Reporter, how he turned to the interludes in Stephen King’s horror novel as the source of inspiration for the series.
“This has a function in the book, obviously. It told me about a puzzle that was intentionally unfinished in the book. Stephen King creates all these enigmas and big question marks to create tension, but for me, it was like, what if this is a blueprint for a different story,” Muschietti explained.
In the novel’s interludes, Mike Hanlon is told by his father about the early sightings of “It,” which prompts him to learn and research the history through interviews with the older residents of Derry.
“He wrote all this. The interviews are documented. That is a product of his investigation, which is a very fragmented document where he compiles all the experiences of people in the past and where he tries to basically figure out what ‘It’ is, but it’s inconclusive,” he continued. “We are left with more questions than answers.”
Muschietti described the show as telling “a hidden story, a story that is not told forward but a story that is told backward and has a final conclusion — the events in which ‘It’ becomes Pennywise.”
Watch IT: Welcome to Derry on HBO Max
It (2017)
Brooke Palmer/Warner Bros.
It takes place in the summer of 1989 and centers around a group of outcast kids less than a year after the tragic disappearance of Georgie Denbrough. Still haunted by his younger brother’s disappearance, Bill Denbrough and his friends, who name themselves the Losers Club, attempt to investigate things, only for them to each soon be tormented by various versions of Pennywise.
After some research, they determine that “It” is playing on their worst fears, and reappears every 27 years to feed on the children of Derry before going back into hibernation in the sewers.
The film stars Jaeden Lieberher (Bill), Jeremy Ray Taylor (Ben Hanscom), Sophia Lillis (Beverly Marsh), Finn Wolfhard (Richie Tozier), Chosen Jacobs (Mike Hanlon), Jack Dylan Grazer (Eddie Kaspbrak) and Wyatt Olef (Stan Uris).
Watch It on HBO Max
It Chapter Two (2019)
Brooke Palmer/Warner Bros.
After leading separate lives, the Losers are reunited in Derry 27 years after the fateful summer of 1989 in It Chapter Two when Pennywise makes a comeback. Although they are grown up, the return of Pennywise brings back painful trauma from their past that they have to fight through to defeat him for good.
Once again, the Losers are forced to confront their fears being manifested by Pennywise. The film stars James McAvoy (Bill), Jay Ryan (Ben), Jessica Chastain (Beverly), Bill Hader (Richie), Isaiah Mustafa (Mike), James Ransone (Eddie) and Andy Bean (Stan).
Watch It Chapter Two on HBO Max
