While Flagg always has the same flavor in most of his appearances, he is, at his core, a chameleon, which is why it's been so easy to incorporate him into so many works, whether just on the edges or right at the center of the narrative. Through his centuries, he's been a sorcerer and magician, a confidant and betrayer, a demonic figure and a seeming liberator, but one thing is certain: where Randall Flagg goes, death follows in Stephen King's books. The table and article below drive home just how far-reaching and vast the shadow he casts.

1 The Dark Man

1969

Those reading this might be thinking, "What? That's not Randall Flagg's first appearance in Stephen King's books." And in that - his books - you would be correct. However, the Stephen King poem was the earliest iteration and inception of Randall Flagg, though not yet what he would become. According to King, the poem was scribbled on the back of a placemat when he was still a college student at the University of Maine, where it was published in the school's literary journal, Ubris, in 1969 and then in Moth magazine in 1970.

Interestingly, though Flagg was not yet the full villain he was in later stories, certain trademark elements were already fixed in King's mind. King has often said that he had a vision of a man dressed in a denim jacket and cowboy boots, the outfit that became his best-known look from The Stand. The titular "dark man" of the poem was also a malevolent outsider, always traveling and walking the roads - the Walkin' Dude even then - leaving hurt and death in his wake. Later, "The Dark Man" was reprinted in 2004, then again in 2013 with illustrations by Glenn Chadbourne; King also later included it in his 2016 nonfiction book Five to One, One in Five.

2 The Dark Tower: The Gunslinger

1982

While the name Randall Flagg is most associated with The Stand, the character himself is a thread that binds all of King's magnum opus, The Dark Tower series, together. Even though the Crimson King is the villain behind Randall Flagg in The Dark Tower, the latter is the most impactful villain in the series and as important as Roland himself, albeit under different guises.

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Beyond just being Stephen King's best villain, period, the sorcerer specifically proves a worthy adversary for Roland, as wily as the gunslinger is determined. He drives much of the plot of the first book and, thus, the series itself. It's fitting that what ended up becoming King's vast, interconnected universe all began with, "The man in black fled across the desert and the gunslinger followed."

3 The Dark Tower II: The Drawing Of The Three

1987

The man in black continues as the sequel's overarching antagonist, though, unlike in The Gunslinger, he remains unseen in the second book in the present day (though he does appear in a flashback). Despite not appearing directly on the page, it's his tarot reading of Roland's future at the end of the first book that puts the gunslinger on his path and drives the events of the second. In this way, the man in black starts to take on the persona Randall Flagg has often adopted across Stephen King's books - that of a puppetmaster and villain manipulating everyone from behind the scenes.

4 The Dark Tower III: The Waste Lands

1991

Randall Flagg reappears on the page in The Waste Lands, albeit with yet another name and another guise. This time, the identity he takes is Richard Fannin, a supposed dark gunslinger with black hair and cruel looks. In a relationship akin to the manipulative master-servant one he shared with the troubled Trashcan Man in The Stand, Fannin manipulates the Tick-Tock Man, a mentally unstable man once known as Andrew Quick. Fannin takes advantage of Tick-Tock Man's enmity towards Roland and his ka-tet, convincing his new acolyte that it's up to him to stop Roland's crew from reaching the Tower, again illustrating Flagg's knack for finding and preying on the weak.

5 The Dark Tower IV: Wizard And Glass

1997

Wizard and Glass is the one book that really begins to show Randall Flagg's far-reaching and long-running influence on Roland Deschain's life and fated journey to reach the Tower, and thus, Flagg's influence on Stephen King's entire interconnected universe. In the fourth book's story within a story framing, Flagg plays a prominent role in both the past and present.

In the past, he's known as Marten Broadcloak, the untrustworthy advisor of Roland's father and whose betrayal starts Roland on his path to becoming a full gunslinger. In the present, he has another run-in with Roland and his friends, revealing these identities have always been his and that he's been moving the gunslinger like a chess piece all along.

6 The Dark Tower V: Wolves Of The Calla

2003

While he's not the primary antagonist in Wolves of the Calla, Randall Flagg continues to influence the events off the page. The sorcerer pops up in a flashback scene to cross paths with one of Roland's future ka-tet, once again offering a poisoned chalice of a gift, meant to spring a trap in a future only he can see.

This time, it's Donald Callahan of 'Salem's Lot, who reappears in the Dark Tower books. He tells of his life as a vampire hunter after the events of 'Salem's Lot, including his seeming death. Yet he wakes up, still alive, in a Way Station. There, a man named Walter o'Dim - of course, Randall Flagg - gives him the Black Thirteen, a powerful, cursed ball that, unbeknownst to Callahan, Flagg one day hopes will kill Roland and lead to his destruction.

7 The Dark Tower VI: Song Of Susannah

2004

Flagg is again unseen in Song of Susannah, and even pulls back a bit as the primary antagonist, though his influence is still felt. In truth, he doesn't need to appear, as his plan is already set in motion. The Black Thirteen is stolen by Mia, a succubus who takes control of Susannah's body, intending to use her as a vessel to birth the were-spider Mordred Deschain.

In a story ripped straight from Arthurian legend, Mordred is Roland's part-son and destined to kill him. Meanwhile, the Black Thirteen starts working its evil influence, almost causing Jake and Callahan to murder each other when they find it before Callahan's prayers put it to sleep, enabling them to lock it away.

8 The Dark Tower VII: The Dark Tower

2004

The man in black/Walter appears for the final time in the series' chronology in The Dark Tower – at least, the last time that's written on the page. His final gambit is his most audacious of all: trick the incredibly powerful Mordred into opening the Dark Tower's door for him, whereupon Walter would install himself on the top level and become the God of All. But Walter's fatal miscalculation is underestimating how powerful Mordred truly is. The monstrous boy senses Walter's manipulation and psychically enters Walter's mind, forcing the sorcerer to rip out parts of his own body, which Mordred then consumes before killing him.

"He pounced upon Randall Flagg, Walter o’ Dim, Walter Padick that was. There were more screams, but only a few. And then Roland’s old enemy was no more."

– The Dark Tower

In one last twist, however, it's revealed the Dark Tower series is a repeating time loop, so it's entirely possible that Walter survived. Considering his history, he almost certainly did - somehow.

9 The Dark Tower: The Wind Through The Keyhole

2012

There is one more Dark Tower story in which Randall Flagg appears, though it's an out-of-chronology, standalone story that, in the timeline, slots between Wizard and Glass and Wolves of the Calla. The Wind through the Keyhole is another story where a young Roland, early in his career as a gunslinger, does not realize the man in the tale he's relating is actually Walter/Flagg.

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In his story, which is framed as something of a fairy tale, the character, who is obviously Flagg, goes by the name The Covenant Man. Flagg once again plays the puppetmaster by manipulating events throughout. Though the story doesn't even happen to Roland himself, it's another example of the subtle ways that the sorcerer influenced Roland's life from a young age.

10 The Stand

1984

If The Dark Tower series is the one work Randall Flagg is most closely associated with, The Stand is the other. The 1978 post-apocalyptic epic is not only one of Flagg's most well-known appearances, it's also his first. King intended for Randall Flagg to be his version of a Satanic figure, a demonic trickster who influences wayward souls to great acts of evil. He does exactly that in a version of America that has been decimated by the superflu, calling to certain darkly chosen ones to him in Las Vegas to build his new hell on earth. While he's not the devil, his good and righteous counterpart, Mother Abigail, explains he might as well be.

“'He ain't Satan,' she said, 'but he and Satan know of each other and have kept their councils together of old.'”

- The Stand