Irving chose for his setting the twenty years that embrace the Revolutionary War because the numerous social and political changes that took place then enabled him to bring Rip back after his sleep into a “world not realized.”  You will appreciate much better the art of this time-setting if you will try your hand on a somewhat similar story and place it between 1820 and 1840, when railroads, telegraph lines, and transatlantic steamers made a new world out of the old; or, if your story takes place in the South, you might make your background include the interval between 1855 and 1875, when slavery was abolished, when the old plantation system was changed, when the names of new heroes emerged, and when new social and political and industrial problems had to be grappled with.

Plot.  The plot is divided into two almost equal parts, which we may call “before and after taking.”  A recent critic has said:  “The actual forward movement of the plot does not begin until the sentence, ’In a long ramble of the kind on a fine autumnal day, Rip had unconsciously scrambled to one of the highest parts of the Kaatskill Mountains.’” The critic has missed, I think, the main structural excellence of the story.  Dame Van Winkle, the children who hung around Rip, his own children, his dog, the social club at the inn with the portrait of George the Third, Van Bummel, and Nicholas Vedder, all had to be mentioned before Rip began the ascent of the mountain.  Otherwise, when he returned, we should have had no means of measuring the swift passage of time during his sleep.  Each is a skillfully set timepiece or milepost which, on Rip’s return, misleads the poor fellow at every turn and thus produces the exact kind of “totality of effect” that Irving intended.  The forward movement of the plot begins with this careful planning of the route that Rip is to take on his return trip, when twenty years shall have done their work.  Cut out these points de repere and see how effectively the forward movement of the plot is retarded.

Characters.  Rip was the first character in American fiction to be known far beyond our own borders, and he remains one of the best known.  In the class with him belong James Fenimore Cooper’s Leatherstocking (or Natty Bumppo), Harriet Beecher Stowe’s Uncle Tom, Joel Chandler Harris’s Uncle Remus, and Mark Twain’s Huckleberry Finn and Tom Sawyer.  He has been called un-American, and so he is, and so Irving plainly intended him to be.  If one insists on finding a bit of distinctive Americanism somewhere in the story, he will find it not in Rip but in the number and rapidity of the changes that American life underwent during the twenty years that serve as background to the story.  George William Curtis calls Rip “the constant and unconscious satirist of American life,” but surely Irving would have smiled at finding so purposeful a mission laid upon the stooping shoulders of his vagabond ne’er-do-well hero.  Rip is no satirist, conscious or unconscious.