Let's say that there's a work B, which under U.S. law seems to count clearly as a transformative use (parody, satire or the like) of another work A, and thus subject to fair use. So what about a work C that is a (licensed) derivative work of B? Would it also need to count as a transformative use of A for it to be fair use?
The analysis is always with respect to the work that the owner is claiming infringement of. Work C would be compared to work A.
The copyright owner would have to prove copying happened (even via an intermediary, like work B). The copyright owner would also have to prove that work C included a substantial taking of the original work in A.
The owner of work C could raise a fair use defense, and work C would be subject to the 4-factor fair use test in relation to work A.