Kitt, because it's all about The Voice

There needs to be an episode where a Klingon, a Romulan, a Gorn, and Harry Mudd sit around a table and recount the time they almost killed Captain Kirk.

Edit: Replaced Tholian with Gorn, more appropo.

Nope. That's the CBS Paramount boardroom.

I think that’s Lee Meriwether as Catwoman in this shot. It looks to be from Batman: The Movie.

Eartha Kitt was better in the role, but censorious suits forced them to tone down the romantic attraction between her and Batman. So Newmar had better material, which might mean she wins by default, depending how you make your judgement.