How to legally use a celebrity likeness

I don't know the answer to this, but I imagine that this guy would:

http://www.strebecklaw.com/

He does a lot of different blog posts related to board games and legality, and seems pretty happy to help. You may get a sales pitch, but I think it's worth dropping a line.

This should help: https://www.fenwick.com/publications/Pages/Litigation-Alert-Transforming...

The key point is "media can appropriate aspects of a celebrity's likeness so long as they are sufficiently combined with new and different characteristics." Personally, I do not think that your caricatures meet this criteria. Even as someone disinterested in wresting, I could readily identify each likeness. Their signature characteristics are intact without any recombination. So, for example, give Steve Austin a koala and an outback hat, and call him Steve Aussie.

Yet. Numerous kickstarters have appropriated all sorts of likenesses without permission or consequence, probably because this is such a penny-ante industry that such misappropriations remain below the radar. You could do the same. However, you don't want that axe hanging above your head. The more successful your game is, the more likely that axe will fall, and litigation is a bitch. Even a victory in court can leave your company bankrupted by legal fees. Personally, I'm waiting on the KS that proves to be the straw that breaks the camel's back, unleashing a torrent of litigation against all of these companies that thought it was okay to steal a likeness if they switched up the name a little. What I've seen in other industries is that it is more cost effective to drop the hammer of god with multiple lawsuits to set an example than to pursue individual suits on a case-by-case basis as they arise. However, if you aren't sued within six years of publication then you at least have laches as an equitable defense against injunction, and a strong case against damages since a reasonable amount of time would have passed. I'm anxiously waiting to see if Zombicide can pass that hurdle.