Hi Heather,
As long as your artwork is entirely derivative rather than copied you should be fine. But you need to be constantly on the lookout for unconscious copying. However, you mention logos (and by extension I assume you will also want to use advertising slogans), which in addition to being covered by copyright, may also be registered as trade marks. That said registration of old marks lapses after 10 years if not renewed and in any case lack of use in the course of trade for a continuous period of 5 years is usually sufficient for a current registration to be revoked
Using images under licence from picture agencies such as Shutterstock would be much safer, but make sure that you get the right sort of licence for your proposed usage. You can end up paying far more than you need to for a licence which is too broad, so if in doubt ask the agency for advice.
The words 'We'll meet again' are not protected by copyright even though they form part of a famous song, the lyrics of which are still in copyright (and will be until 2066). This is because this short phrase falls into the
de minimis category - too trivial for the courts to be bothered with. Also there is only one registered trade mark containing these words, but unless you intend to use the words
in connection with clothing, that will not present any problems. Similar constraints may apply to other song titles and advertising slogans, although if only a few words are involved (especially if they are the title of the song), the problem of copyright infringement can usually be ignored.
Since I assume that you will be dealing mainly with well-known and iconic images etc from the past, the task of finding current owners of any copyright in them should be somewhat easier as these will tend to be among the better documented items. Specialist museums (such as the
Museum of Brands, the V&A and so on) may be able to help, and you will find that there are many collectors groups (eg
Poster Collectors) with a wealth of knowledge on extremely esoteric subjects - you just need to google the right phrases to find them. If you can track down the current owners of the assets of a long defunct company, getting permission to use their old material for this purpose shouldn't be too difficult.
