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I think that the copyright battle is being fought more over movie and music copyright than over book copyright. Steamboat Willie came out in 1928, so we still have a few years before Disney gets worried.
From a movie, music point of view, I don't think we will see any big movement until the movies from the mid to late 30's come up (especially 1939). From a book point of view, I'm trying to think of a book that is worth enough money to fight over. The Hobbit came out in 1937. Maybe Gone With the Wind or some of the Agatha Christie books.
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