So, there are some really weird cases that lead to very interesting lawsuits. Sherlock Holmes was involved in one: A derivative was made based on early books be

So, there are some really weird cases that lead to very interesting lawsuits. Sherlock Holmes was involved in one: A derivative was made based on early books becoming public domain, and the estate sued them because they felt aspects of his character shown in the derivative work wasn't actually added until a later book which was not yet in the public domain. https://www.theverge.com/2020/6/25/21302942/netflix-enola-holmes-sherlock-arthur-conan-doyle-estate-lawsuit-copyright-infringement https://www.theverge.com/2020/6/25/21302942/netflix-enola-ho... Which is to say, if you happen to put a red shirt on your Pooh rip-off, it's very likely Disney can, and will, sue you. This alone means that if you want to adapt Pooh (or Steamboat Willie), you probably need to go a very different direction than Disney has, such that the character is not likely to be recognizable as the same.