Every Stephen King Book With Randall Flagg, Ranked

Image via Marvel Comics Published Aug 29, 2026, 5:14 PM EDT Jeremy has more than 2700 published articles on Collider to his name, and has been writing for the site since February 2022. He's an omnivore when it comes to his movie-watching diet, so will gladly watch and write about almost anything, from old Godzilla films to gangster flicks to samurai movies to classic musicals to the French New Wave to the MCU... well, maybe not the Disney+ shows. His favorite directors include Martin Scorsese, Sergio Leone, Akira Kurosawa, Quentin Tarantino, Werner Herzog, John Woo, Bob Fosse, Fritz Lang, Guillermo del Toro, and Yoji Yamada. He's also very proud of the fact that he's seen every single Nicolas Cage movie released before 2022, even though doing so often felt like a tremendous waste of time. He's plagued by the question of whether or not The Room is genuinely terrible or some kind of accidental masterpiece, and has been for more than 12 years (and a similar number of viewings). When he's not writing lists - and the occasional feature article - for Collider, he also likes to upload film reviews to his Letterboxd profile (username: Jeremy Urquhart) and Instagram account. He has achieved his 2025 goal of reading all 13,467 novels written by Stephen King, and plans to spend the next year or two getting through the author's 82,756 short stories and 105,433 novellas. Sign in to your Collider account Randall Flagg has some tough competition if you're talking about the scariest or most iconic villain in any Stephen King story. Like, the titular villain from IT (sometimes referred to as Pennywise) might well be more frightening, and then Annie Wilkes from Misery is also highly memorable, considering she doesn’t have any otherworldly or supernatural powers. It also helps that those villains have been made more iconic thanks to TV and film performances, with Tim Curry and Bill Skarsgård both being great in different adaptations of IT, and Kathy Bates giving an absolute all-timer of a performance as Annie in Misery (1990). Flagg’s also been portrayed on screen, by Jamey Sheridan, Matthew McConaughey, and Alexander Skarsgård, all in different adaptations, but the character’s never really been in a great movie or TV series, unfortunately. He dominates on the page, though, and he has both IT and Annie Wilkes beat in terms of appearances, since he shows up, in one way or another, in nine novels by Stephen King. There are other times he’s mentioned, and a few characters in other stories who are sometimes theorized to be Flagg (he’s a man who goes by many names and all), but these are the books he’s definitely in, and those nine are ranked below. 9 'The Dark Tower: The Wind Through the Keyhole' (2012) Image via Scribner Book Company The main The Dark Tower series is made up of seven main books, and The Wind Through the Keyhole isn't one of them. Instead, it’s more of an interquel, with it taking place between books #4 and #5. Roland tells his ka-tet a story, and then within one of those stories, there’s another story. It’s a story about storytelling, and the stuff with Roland and the other familiar characters is more there as a framing device. You don’t get a ton of Roland, Jake, Eddie, Susannah, or Oy here, and you also don’t get a ton of Randall Flagg in The Wind Through the Keyhole. He is a figure within the story Roland initially tells, though (going by one of his aliases: Marten Broadcloak), so with that story within the overall story being important, this interquel does still count as a novel with a Flagg appearance… mostly. Look, it felt more sensible to include it than not include it. 8 'The Dark Tower VI: Song of Susannah' (2004) Image via Donald M. Grant, Publisher The Dark Tower VI: Song of Susannah stands as the weakest of the books in the mainline The Dark Tower series, so long as you're not including The Wind Through the Keyhole. It at least feels a bit more impactful on a narrative front than that one, even if it’s pretty set-up heavy, and with only a few moderately dramatic moments. The big dramatic moments, on the other hand, come through heavily in book #7, largely thanks to Song of Susannah putting all the pieces in order first. As for Randall Flagg, his appearance here is brief, and in a flashback, but it is important, since that flashback helps establish how the horrifying Mordred Deschain (with his two fathers and two mothers) came about. And Mordred, for better or worse, is significant to that final book, too, and has some scenes in that finale with Flagg that could be called “interesting.” 7 'The Dark Tower: The Gunslinger' (1982) Image via Donald M. Grant, Publisher No one’s going to mistake The Dark Tower: The Gunslinger as hard science fiction or anything, but there is some sci-fi here, alongside various other genres, and it was the first book in the series, so the blending of genres feels particularly surprising here (naturally). This first book is also perhaps the one where Flagg plays the biggest role, and he’s even in the novel’s famous opening line: “The man in black fled across the desert, and the gunslinger followed.” That’s more or less the plot, too, with the man in black sometimes going by that name, and sometimes going by Walter O'Dim, while the gunslinger referred to is, of course, Roland. Randall/Walter is important at the start, significant throughout, and then definitely essential for the final sequence of the book, which sets up book #2 and seems to have Randall/Walter dying… but it turns out he faked his death. Hey, how else would he still be important for Song of Susannah, which was already mentioned? 6 'The Dark Tower III: The Waste Lands' (1991) Image via Donald M. Grant, Publisher So, The Drawing of the Three was skipped over, because that’s the only book in the series that Randall Flagg doesn’t really appear in, even briefly. He is mentioned, though, for what that’s worth, in another flashback, because Roland mentions how he remembers meeting two people who were pursuing Flagg (this ties into The Eyes of the Dragon, and the way that book ends, but more on that one later). He goes by Richard Fannin, and appears near the end of The Waste Lands in a way that’s surprising, given what happened to him at the end of The Gunslinger. That means The Waste Lands is the next time Flagg properly appears, and as for this book, it also happens to be slightly better than the previously-mentioned Dark Tower books (albeit not as great as the ones to come). He goes by Richard Fannin, and appears near the end of The Waste Lands in a way that’s surprising, given what happened to him at the end of The Gunslinger. But it’s definitely Flagg, and he allies with an enemy of Roland’s ka-tet named Andrew Quick… again, near the book’s end, so all this is important for book #4 in the series. Speaking of… 5 'The Dark Tower IV: Wizard and Glass' (1997) Image via Donald M. Grant, Publisher This is all going to sound a bit gonzo if you've not read Wizard and Glass, but that stuff with Randall Flagg and Andrew Quick? It’s developed in the final few chapters of this fourth book, and it all happens within what looks like part of The Wizard of Oz. You just have to roll with it, especially since book #5 will see the references to other stories intensify. Randall Flagg is confident about going by that name in Wizard and Glass, and his confrontation here with Roland is their first proper one since The Gunslinger, so that does ensure the book ends on an appropriately dramatic note. The rest of Wizard and Glass, though, is a bit more laidback, or at least slower-paced, with Roland telling the ka-tet an extended story about his past... but Flagg as Walter O'Dim also had some role in certain tragic events that take place within Roland’s past. 4 'The Dark Tower V: Wolves of the Calla' (2003) Image via Donald M. Grant, Publisher When you take out The Drawing of the Three, The Dark Tower really is a series that gets better from book #1 to #3 to #4 to #5, so here’s book #5, conveniently in (relative) order. The Drawing of the Three is probably superior to those other books, though, so if you're doing a whole ranking of The Dark Tower, it wouldn’t be quite as simple. Anyway, Wolves of the Calla. Book #5. This one’s also a bit weird. Stories matter in this one a lot, but not necessarily Roland’s stories, like with Wizard and Glass and The Wind Through the Keyhole. Other stories, like Harry Potter and Seven Samurai, invade into Wolves of the Calla. There are also Doctor Doom masks there in a big way, which is funny now, with hype building (at the time of writing) for Avengers: Doomsday. As for Flagg, he’s not in this much, outside an interaction with Father Callahan, who appears here (and in the next two Dark Tower books) after being a significant character in King’s Salem’s Lot (1975). The multiverse expands. 3 'The Eyes of the Dragon' (1984) Image via Viking Press While it’s not an outright comedic book by any means, The Eyes of the Dragon is a fair bit lighter than the other books being mentioned here. It’s King almost tackling the young adult genre, making it teenager-friendly, or maybe even for some older kids. Randall Flagg only goes by Flagg in this one, but he’s pursued by some characters post-The Eyes of the Dragon, as The Drawing of the Three showed, so it’s the same Flagg. But King Roland, in The Eyes of the Dragon, is not the same Roland as the gunslinger, since King Roland’s death kicks off the main plot of The Eyes of the Dragon, which involves Flagg trying to rule the kingdom by manipulating one of Roland’s children and imprisoning another. It takes place in the realm of Delain, which is another place Flagg wanted to cause chaos and destruction alongside Roland’s realm and Earth (the latter being where Randall Flagg does a lot of damage in a certain novel published in 1978… and then republished in 1990, in an uncut version). 2 'The Dark Tower VII: The Dark Tower' (2004) Stephen King books don’t get too much more important than The Dark Tower VII: The Dark Tower, since this concludes the author’s biggest and most ambitious series. Randall Flagg is one of many characters who does prove important here, but Flagg might not be as vital as you'd expect, since this final book is an opportunity for the Crimson King to come into focus as, more or less, the final antagonist. “More or less” because he also might not have the role you'd expect. Also, the Crimson King is mentioned very often throughout The Dark Tower, and plays roles in some other Stephen King books, but Flagg probably has more direct appearances, or “does more” actively, while the Crimson King often remains shrouded in mystery. There’s still a lot not known about him, but The Dark Tower VII does give those villains some time to shine, while also giving the previously mentioned Mordred a surprising amount of time to shine. It’s all very strange and oftentimes subversive, but in ways that mostly work (and this is easily one of King’s most emotional novels, too). 1 'The Stand' (1978/1990) Image via Doubleday The first appearance of Randall Flagg was in The Stand, and it remains his most memorable performance. And The Stand happens to be the best book that Flagg’s a part of, or even right up there as one of the best Stephen King novels, if not the best Stephen King novel. So, The Stand going in the #1 spot here is an easy choice on every front. It is a quintessential post-apocalyptic book, and the most epic-in-scale single book of King’s (The Dark Tower is more sprawling, but it also has multiple books to tell that larger story). Randall Flagg is at his most intimidating in The Stand, too. He’s a solid antagonist in The Dark Tower and The Eyes of the Dragon, but he seems a bit more vulnerable – and not quite as powerful – in those books. He’s got his shortcomings and things that threaten to undo him in The Stand, too, but when he’s loose in a world where more than 99% of the population has been killed, and about half of those who remain seem willing to follow him as some kind of messiah, then he’s suddenly more of a threat. He’s arguably a little more disturbing in the uncut version of The Stand, too, thanks to the implication of that 1990 edition’s epilogue. The Stand Release Date 1994 - 1994-00-00 Directors Mick Garris