WARNING: Spoilers for IT Chapter Two.
Despite Pennywise (Bill Skarsgard) one last time. IT Chapter 2 is definitely more modern than the original film but it's still, technically, a period piece.
In IT Chapter 2, Mike Hanlon (Isaiah Mustafa) summons his old friends back home to honor the vow they made as children after they originally defeated Pennywise. Bill Denbrough (James McAvoy), Stanley Uris (Andy Bean) the lone holdout. Although the IT movies are set decades later than what's depicted in Stephen King's novel, they still adhere to the basic rules that Pennywise returns 27 years after the Losers face him as kids.
Since the original movie's events occurred in the summer of 1989, IT Chapter 2's main story takes place 27 years later in 2016. This year is explicitly established when Richie sees a program of his own funeral that Pennywise taunts him with (a throwback to the missing child posters that are plastered all over Derry in both IT and IT Chapter 2). That a 2019 release is actually set three years ago may seem rather strange, but there's a clear narrative reason. Were the movie set any later, then the 27 years rule would move IT Chapter 1 into the 1990s, hurting the 1980s nostalgia factor of the original film.
IT Chapter 2's many flashbacks to the summer of 1989 can obfuscate the time period a little bit but the film remains very clear about the progression of time. Young Ben (Jeremy Ray Taylor) is in summer school and listening to New Kids on the Block, the biggest boy band of the late 1980s/early 1990s. In IT, the local movie theater was showing Tim Burton's original A Nightmare on Elm Street 5: The Dream Child, which was released on August 11, 1989 (and was from New Line, just like the IT movies).
Curiously, IT Chapter 2 also does things to confuse its own 2016 setting. At the start of the film, when Adrian Mellon (Xavier Dolan) and his boyfriend Don Hagarty (Taylor Frey) are victimized in a hate crime, Adrian taunts his attacker with Meg Ryan jokes, even though the actresses rom-com heyday was in the 1990s. Later, after The Shining (released in 1980) also feels very slipshod in relevance (although it was purposely a nod to Stephen King, who wrote the novel).
Regardless of IT Chapter 2's lack of consistency about its 2016 setting (there is no mention, for example, of the 2016 election in Derry), the sequel's year is locked in to be 27 years after 1989. Ultimately, it means that no matter what, the IT saga occurs in our past. And, since Pennywise was killed by the Losers, if there's another IT movie, it could likely be a prequel about the evil clown's infection of Derry in the 1800s, setting it even further back in the past.
