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SYFY WIRE Pennywise

Stephen King stirs the pot on whether Pennywise and Randall Flagg are the same entity

The master of literary horror seemed to suggest on Twitter that both iconic villains are one and the same.

By Josh Weiss
(L-R) Pennywise from It (2017) and Randall Flagg from The Stand.

Stephen King, the unparalleled master of literary horror has stirred up quite the raucous within his own fandom by way of a single tweet that suggests two of the author's most iconic villains — Pennywise (IT) and Randall Flagg (The Stand) — are the same being.

"Screen Rant asks the question America cares about most (not): Who is the greater villain, Randall Flagg or Pennywise," King tweeted, referencing a recent article published by the entertainment website. "Have they not considered the possibility that THEY ARE THE SAME ENTITY?"

Of course, King may have been joking at Screen Rant's expense, but if the post is meant to be dead serious (or in this case, Deadlights), then it adds another fascinating wrinkle to the ever-expanding supernatural mythos contained within King's many works.

Flagg, for instance, has enjoyed a massive presence outside the events of The Stand as the Man in Black of the Dark Tower universe. Pennywise, on the other hand, has cropped up in other books and stories over the years via tangential references intended to serve as subtle fan service rather than major plot points. If Flagg is indeed the same cosmic horror lurking beneath the streets of Derry, Maine...well one must come to the conclusion that The Walkin' Dude (another nickname for the Vegas-ruling despot) is one of the most — if not the most — powerful and omnipresent entities throughout the entire Stephen King-Verse.

On the surface, the similarities are uncanny: Pennywise and Flagg have a talent for using otherworldly abilities to mess with — and in some cases, destroy — the human mind. Perhaps unintentionally furthering the kinship between the antagonists is the fact that both were recently played onscreen by a pair of brothers: Bill Skarsgård (Pennywise in Andy Muschietti's IT films) and Alexander Skarsgård (Flagg in The Stand miniseries on CBS All Access). The former may be returning to Maine in an IT prequel series currently in active development at HBO Max.

“Writers must be fair and remember even bad guys (most of them, anyway) see themselves as good — they are the heroes of their own lives," King told Writer's Digest back in 2009. "Giving them a fair chance as characters can create some interesting shades of gray — and shades of gray are also a part of life."