The poster case is classic copyright and is about what almost all copyright cases are about; money and credit. It’s not whether a head angle can be copyrighted, copyright only prevents copying not independent creation. It’s whether the artist infringed the right of the photograph owner by copying the photo and/0r preparing a derivative work (another right granted to owners). The artist’s defense was originally that he didn’t copy (that appears to be a lie) but his better and more interesting defense is fair use. It’s actually a fairly close case and very interesting case.

The trademark case above, has nothing to do with trademark law but rather someone using trademark law to sustain an otherwise unsuccessful action intended to silence critics.

You are wrong on the Wind Done Gone. The 11th circuit found that it was parodic in nature and that the publisher was entitled to a fair use defense.