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At the end of The Eyes of the Dragon, there's a line about how Dennis and Thomas meet Flagg again...I always assumed that happened in the Dark Tower series, but I'm still reading the Gunslinger.
There's also a bit about how Flagg is pretty much immortal, so I think it's not a huge jump to say Flagg the Wizard, Randall Flagg, and the "dark man" are all the same person (or creature, which might be more appropriate.)
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"...for though she was ordinary, she possessed health, wit, courage, charm, and cheerfulness. But because she was not beautiful, no one ever seemed to notice these other qualities, which is so often the way of the world."
"Tell me, what is it you plan to do with your one wild and precious life?"
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