Every Hidden Pennywise From IT Chapter 1 & 2

8. Bob Gray - It Chapter Two

The most obvious of the sightings in the second movie features a callback to a couple of Easter Eggs in the first film and one of It's favourite manifestations from the book.

In the first film, Bob Gray is referenced on the label of the bottle Eddie picks up and breaks inside the Well House and we finally see a picture of him in the sequel when Mrs Kersch tells Bev about her family history. At the same time, Bev looks at an old photograph showing the circus carriage with Pennywise on the side that turns up in the first movie and Bob Gray standing next to it.

It's clearly Pennywise out of makeup, giving away the fact that Mrs Kersch isn't exactly who she claims.