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The answer to your question is fairly complex and depends on the state in question. So let me start with an introduction.
People (including celebrities) have a legal right called 'right of publicity'. Right of publicity is a hybrid between the right to privacy and trademark / property right. This right is based on the concept that a person has the exclusive rights to control and benefit from his/her image and likeness.
The right of publicity protects the pecuniary interest in the commercial exploitation of a person's identity
However this right also has to be balanced with the first amendment rights of artistic free expression.
Every state law is different in how it applies the pecuniary rights a person may have with the first amendment rights therefore there is no one sweeping bright line answer. In California a number of courts have determined that the First Amendment protects the unauthorized use of a trademark in an artistic work when the mark has artistic relevance to the work and does not explicitly mislead the public as to the source or content of the work. When this test was applied, the court found that as long as long there is no implied endorsement there is no infringement of the right of publicity.
What do you mean by "implied endorsement?"
implied endorsement is when the image of the celebrity is used to endorse a commercial product making it as if the celebrity is the one who made that endorsement (e.g drawing Marilyn Monroe on an ad for your company)
typo: "in an ad"
If you're doing an art piece then you should be in the clear
So if I did a drawing of Marilyn Monroe in a T shirt I'm selling and it was in a video?
interesting enough, there is a case with Marilyn Monroe. She was domiciled in NY when she died and NY does not recognize deceased celebrities rights of publicity
so that means the image of her in the white dress standing over a subway grate is public domain?
the image is not because that photo is copyrighted but you can draw her in other settings (drawing her in a similar setting brings up issues of derivative work)
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