Pennywise is about to share Derry with bank robbers. Season 2 of IT: Welcome to Derry drops the show into 1935, and showrunner Brad Caleb Kane gave Deadline the pitch: “It’s a Warner Bros. gangster movie. It’s bank robbers and Hoovervilles and street urchins.”

Kane, who is running the HBO prequel alone now that Jason Fuchs has stepped back, said the writers’ room is well into it. “We’re writing the scripts. We’re about halfway through the writing of the scripts,” he said. “We have a production schedule, we’re greenlit for...