Like Ichabod Crane of Washington Irving's other famous story, "The Legend of Sleepy Hollow," Rip van Winkle is a would-be hero. While he resembles somewhat the Romantic hero who is greatly involved with nature and the enjoyment of its beauty as he loves to wander away from the town, Rip is flawed because he is lazy and immature and unable to deal with reality. In Irving's America, it seems that there is little room for the imagination. For, when Rip returns to town after his twenty-year sleep, he cannot relate to anyone. In his essay "Rip Van Winkle: Rip, Ichabod, and the American Imagination," Terrence Martin writes or Irving's heroes,
They defeat themselves. It would appear that for Irving there is no place, or a very limited place, for the hero of the imagination.....A nation of Rips and Ichabods, Americans might reason, would soon be no nation at all.
Martin further argues that Rip and Ichabod fail as heroes because they do not recognize
‘‘fact and doctrine,’’ which are at once the prerequisite for and the evidence of personal and cultural maturity.
When Rip returns after twenty years, he seeks no "fact and doctrine"; instead his nostalgia for the "drowsy tranquility" of the past overtakes him and he feels as though he has lost his identity:
"I was myself last night; but I fell asleep on the mountain--and they've changed my gun--and everything's changed--and I'm changed--and I can't tell what's my name, or who I am!"
In becoming a new nation, the old colonies as represented by Rip van Winkle and his friends have lost their romantic charm with tales of fantasy and the supernatural. Instead they are replaced with a "bustling disputatious" populace who pass out handbills and harangue arout the rights of citizens.