It: Welcome to Derry season 2 is officially making progress – but it sounds like certain scenes may prove a difficult watch. Season 2 will focus on one of the interludes in King's novel, the Bradley Gang Massacre, and will take place in 1935, 27 years before season 1. Bill Skarsgård plays Pennywise in IT: Welcome to Derry. It: Welcome to Derry season 1 is available to stream now on HBO Max and NOW. Add It: Welcome to Derry to your watchlist on the Radio Times: What to Watch app – download now for daily TV recommendations, features and more.