Both stories ultimately have much in common with folktales, both in their basic plotlines and stylistic aesthetic. The plots are different of course, but they are recognizable all the same: secret deals with the devil or supernaturally long periods of slumber, after all, both make for common folktale motifs. Both stories also carry with them a very strong sense of place, whether it be the swamp outside of Boston in "The Devil and Tom Walker" or the Catskill Mountains in "Rip Van Winkle," and Irving's writing can get veryimagery intensive in trying to paint a picture of these locales. Finally, both stories employ the same omniscient third-person narration (a fact which should not be surprising, given that this is the point of view that most replicates the experience of a storyteller telling a story).

Both stories also employ the use of archetypes and stock characters. Neither Rip nor Tom Walker are particularly complex or three-dimensional: Rip Van Winkle is largely characterized in terms of being a henpecked husband beleaguered by a domineering wife, whereas Tom Walker is chiefly defined by his greed and pettiness (traits that are mirrored in his own wife).

However, even if neither character is particularly complex, the fact remains that Rip Van Winkle is well intentioned and harmless, whereas the same cannot be said about Tom. This difference also heightens the stark difference in tone and themes between the stories they feature in.

"Rip Van Winkle" is primarily about the transition from colonization to independence and the creation of the United States (a moment which Rip has slept through). "The Devil and Tom Walker," on the other hand, is much more focused on the idea of evil, a theme which is perhaps most strongly reflected in the devil's own centrality within the story, as well as in Tom's own road to damnation.