in creating a digital composite of new original digital illustrations of 1000 historical events--including iconic faces, recreated scenes, paintings, photos--how not to infringe on copyrights by referring to existing online images (not scanning and manipulating them in photoshop as in ap vs fairey--rather drawing new images)?
This question is extremely broad. First, is there any copyright in the original image? Something from the 19th century or earlier is almost certainly in the public domain, as the copyright (if any existed) has expired.
Assuming that a work is still subject to copyright, the principles of fair use are almost impossible to apply without seeing the original work and the proposed use of the work. As a guideline, you can see the statute that implements fair use, but it is somewhat sterile unless you have the original work and the proposed use.
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I agree with my colleague. Your question will require a proper analysis and I suggest you hire a lawyer to have that done before making any investment here. It is always wise to remember that fair use is a defense and will not prevent you from being sued if your endeavor does not sit will with the copyright owners you allude to.
Most of us here, including myself, offer a free phone consult.
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When you knowingly utilize copyrighted images without proper permission from the copyright holder, you risk being sued and "Fair Use" does not prevent such a lawsuit. Rather, "Fair Use" is a defense that your lawyers would claim AFTER you are sued.
Moreover, even if you said you just want to reduce the chance that you will be sued, there are no bright line guidelines that we can give you to follow. Whether you would get sued due to any particular image of the 1,000 images that you utilize in your composite would depend on many, many factors, including, but not limited to, the likeness between your image and the original one that "inspired" you. And, even if you don't think there is "enough" of a likeness between your work and the original to deem it a copy of the original versus a work inspired by the original, the author/owner of the work may not agree. For a current case in point, check out the lawsuit brought by Roger Dean triggered by the film AVATAR (link below).
Bottom line: Learn about each event, and create your own, new image to represent it.
Any answer or other information posted above is general in nature and is not intended, nor should it be construed, as legal advice. This posting does not create an attorney-client relationship between you and the posting attorney, and you are urged to engage a qualified attorney who is licensed to practice in the relevant jurisdiction.