Here are 5 reasons why It: Welcome to Derry promises to be the ultimate Halloween binge on OTT. The series transports viewers to Derry, Maine in 1962, years before the events of It and It: Chapter Two. It unravels the town's sinister past. The gloomy streets, eerie whispers and slow-building tension make it the perfect show to watch during the Halloween season. It is ideal for a spooky movie night. Pennywise the Dancing Clown, played once again by Bill Skarsgård, makes a return. This time, the show peels back the layers of his twisted origins.