In the sketch that mimics the paper sailboat scene from the box office-shattering horror movie, Alex Moffat’s Anderson Cooper chases his news program rundown down a New York City sewer drain, where he spots McKinnon’s Conway with Pennywise makeup.
“Kellywise the Dancing Clown” then attempts to lure Cooper into the sewer – or convince him to put her on TV – with the promise of “crazy, crazy quote” like “Okay, Puerto Rico was actually was worse before Hurricane Maria and the hurricane actually did blow some buildings back together.”
Kenan Thompson’s police officer then warns Cooper that “everyday she drags someone into that sewer, down there where the doodies are.” A moment later, Cicily Strong’s Rachel Maddow is shown in the sewer with Kellywise. “You’ll float too, Anderson,” Maddow tells Cooper.
After Kellywise shows Cooper his greatest fears – headlines reading “Trump Re-Elected for Second Term” and “Anderson Cooper Fat” – the clown morphs into Clinton, who tricks the newscaster into reaching into the sewer for a copy of her book What Happened.
Like the movie, the scene comes to a gory conclusion before Cooper wakes up on the CNN set, only to be horrified that his guest is Conway.