The Man in Black: 5 Memorable Appearances of Stephen King’s Most Reliable Boogeyman

The Stand
While he was alluded to in earlier works by King, The Stand marks Flagg’s coming-out party. He appears even as Captain Trips, a devastating flu virus, reduces the world’s population to a small number of survivors. Flagg, sporting jeans, cowboy boots, and a denim jacket, tempts the weak and evil to journey to Las Vegas in preparation for a Biblical good versus evil battle involving a nuclear warhead and many, many pages of text. Even when he’s ultimately defeated by his opposites in the flock of a good-hearted 108-year-old woman named Mother Abagail, it’s not the end for Flagg, who, in an epilogue added to the 1990 extended edition, reemerges as one “Russell Faraday” on a tropical beach somewhere and begins to assemble a new band of followers.

The Eyes of the Dragon
Known here as just “Flagg,” he’s an evil magician providing untrustworthy counsel to the doomed King Roland. It is Flagg’s betrayal that sets in motion the story of this 1986 novel, whoch offers King’s kid-friendly (ish) take on the epic fantasy genre. He murders the queen, poisons the king, and frames the heir to the throne, Prince Peter, for the deed. Trading his jeans for wizard’s robe, Flagg is portrayed as a more traditional, mustache-twirling fantasy villain. At the story’s end, Flagg is defeated, but not killed; he disappears and is pursued by Prince Thomas and his servant Dennis, only to show up many more times in King’s other series of fantasy books…

The Dark Tower series
Flagg is a big presence in the many books, comic-book adaptations, and even the film version of King’s sprawling epic fantasy saga, appearing in multiple guises. As Walter, he is the man who has an affair with Roland the Gunslinger’s mother, setting in motion the downfall of the capital city Gilead. The series literally begins with Roland in pursuit of Flagg, hell-bent on a mission of revenge from the very first line: “The man in Black fled across the Desert, and the Gunslinger followed.” Roland will lose his soul and maybe even his sanity in this pursuit for Walter/Flagg, whom he hopes will lead him to the Dark Tower, the nexus of all universes. Over many individual pieces of fiction set in King’s Mid-World, Flagg has appeared as multiple characters, all serving the Crimson King (though originally they weren’t all intended to be the same character, King clarified matters in a revised edition of The Gunslinger published in 2003). As Walter O’Dim, he appears to be killed before he can take over the highest level of The Tower, but it doesn’t stick.

Hearts in Atlantis
A minor appearance to be sure, but in King’s collection of interconnected Boomer Generation novellas, Randall Flagg is mentioned as Raymond Fielger, the leader of a cult responsible for a bombing at a military recruitment office. Chunks of the book—particularly the first story, “Low Men in Yellow Coats”—are closely connected to the Dark Tower universe, to a degree that plot elements of book seven, The Dark Tower, will prove confusing to readers who’ve never read it; it provides essential backstory on the schemes of the saga’s overarching adversary the Crimson King, whom Flagg serves as a loyal (until he isn’t) lieutenant.

Gwendy’s Button Box
Is Randall Flagg getting soft in his old age? As portrayed in this story of a young girl in possession of a gifted box that can change world events, Flagg appears as Richard Farris, who seems less of an evil monster than simply a representative of elusive forces young Gwendy Peterson couldn’t hope to understand. In the ways that Farris advises, helps, and even seems to admire Gwendy’s innocence, Farris shows King (and co-author Richard Chizmar) imbuing Flagg with the most sympathetic and nuanced portrayal yet. Has Flagg simply been working to maintain the balance of good and evil in the world all this time—a necessary force of nature in a stew of predetermination? We might get more answers in the follow-up, Gwendy’s Magic Feather, a sequel due out from Chizmar in November.
What’s your favorite incarnation of the Man in Black?