Hi Kyro,
Restating your question - is it possible for a creator or commissioned seller of caricature/parody-type images of political or non-political public figures infringe on someone’s legal right or get into criminal issues.
These are the possible minefields:
1. Copyright issue - It is possible for a created work to contain elements of something that is copyrighted by another.
2. Trademark issue - unless it is sufficiently altered a mark as long as it is recognisable may be a problem.
3. Privacy law, child protection, child sex offences - any depiction of a anyone in private setting (and definition of private can be complicated) any child (e.g. children of famous people) especially with sexual connotation - just no. Possible criminal issue.
4. Defamation issue - especially with work to politicians it is possible for them to try to sue for such images. Will the suit be successful - would depends on a number of complex legal issues but generally the defences would be for example - there is no defaming of character because it is real, or it is a fair representation, or that it is sufficiently trivial.
Practically, 1-3 are pretty straight-forward to avoid but whether or not a product is defamatory - it is probably something that needs a private solicitor to assess.
Good luck!
-Nighthelyn
This post contains general information about legal matters. The information provided is not advice, and should not be treated as such. This answer does not create a solicitor-client relationship, nor is it a solicitation to offer legal advice. The information is provided “as is” without any representations or warranties, express or implied. The information should not be relied upon in place of professional legal advice.