You might begin exploring "Rip Van Winkle" through the "reader response" approach. Ask students which characters are sympathetic and why. Some students will see Rip's flexibility as admirable and his oppression by Dame Van Winkle as pitiable, while others will see Rip as a good-for-nothing. Explore how these different points of view change interpretations of the story: is it good or bad to sleep through catastrophic historical change? To what extent should the masses actively be involved in the construction of society?
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