Contact Playboy to find out if they will license the images to you. I expect none are in the public domain and all belong to the publication or its photographers. Moreover the models undoubtedly have rights of publicity in the depictions of their likenesses which would be implicated by the use you contemplate. Expect to get into expensive hot water if you proceed in the course of action you describe without explicit permission from the copyright holders.
Not legal advice as I don't practice law in New York. Consult New York counsel if you need legal advice. I practice in Vermont ONLY.
No. Or at least, highly unlikely. Although pre-1978 published works don't get the life of the author plus 70 year rule, with renewals they can be protected for 95 years. I highly doubt that Hef has let any slip by.
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I agree with my colleagues. Unless Playboy provides you a license to use their images, it is possible that you would be subjecting yourself to a cease-and-desist action one day. Tread carefully and good luck.
Yes copyright applies to items registered before 1978 if, in the situation relevant here, the registration existed in 1978, as the 1978 law extended those registrations to life of author plus 70 years or, in the case of a company (here Playboy Enterprises) or if the date of death is unknown, to 95 years. I think you need to get permission or wait until 2062-2069.
See a copyright lawyer for obtaining permission or to try to find other workarounds.
I am not your lawyer and you are not my client. Free advice here is without recourse and any reliance thereupon is at your sole risk. This is done without compensation as a free public service. I am licensed in IL, MO, TX and I am a Reg. Pat. Atty. so advice in any other jurisdiction is strictly general advice and should be confirmed with an attorney licensed in that jurisdiction.
This is clearly illegal. Copyright law applies to photographs created before 1976 provided the copyright owners complied with various formalities, such as registration and notice. You can be certain that Playboy complied with these formalities and protected its copyrights in these photographs. In addition to violating copyright law, you would almost certainly be violating trademark law and engaging in unfair competition. Your proposal to "alter" the image means that you want to create a derivative work---unless your work is transformational (and your work almost certainly will not be), you need a license to create a derivative work. You are asking for a law suit if you pursue this obviously illegal idea.