March 10, 2025, 2:49pm

For our Villains Bracket week, a few Lit Hub staffers wrote a little bit on their favorite villain from our initial group of 64. Here’s Drew on Randall Flagg from Stephen King’s work.

“The man in black fled across the desert, and the gunslinger followed.” Say thankee, there are few sentences, opening or otherwise, that will live as strongly in my mind until the end of time as that one. The gunslinger, of course, is Roland Deschain—but who is the man in black? Walter o’Dim, they call him, or Marten Broadcloak, but really he is Randall Flagg (or any number of RF permutations) and he is Stephen King’s great villain.

More than that, he’s the lynchpin across King’s multiverse, perhaps even more so than the Dark Tower itself. He is the primary antagonist of The Stand, the central evil of that book and a repellent one for certain, but it is his turn across The Dark Tower series that makes him truly memorable. Willing for a conversation, always with a trick or three in mind, a schemer and a dreamer and a villain through a through. A wizard, a necromancer, the chief agent of the Crimson King, an entity somehow encapsulating aspects of villains from Moriarty to Blofeld but walking in a distinctly American shape regardless of the time or place.

The way King describes first thinking of him, “this guy in cowboy boots who moved around on the roads, mostly hitchhiking at night, always wore jeans and a denim jacket,” has been splashed across American speculative fiction ever since—and though good often triumphs in King’s work, Flagg’s own eternal recurrence reminds the reader (as so many of the best villains do) that the darkness keeps coming back in new and different forms. After all, ka is a wheel.

And here’s Drew’s entire bracket: