Why is it legal to buy and sell used books/discs but illegal to buy and sell used digital files?

this contradiction always confused me. either way the official company is "losing a sale" and not getting the money, right?

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If they could, they would. Laws aren't passed because it makes sense, but because they benefit the rich.
- "The law, in its majestic equality, forbids the rich as well as the poor to sleep under bridges, beg in the streets and steal loaves of bread."
  
  -Anatole France

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