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If the captive is inside one the areas behind the door with little black tentacles coming out of the edges, then once you exit it, it cannot be went back in. It's been a while and I don't remember if any are behind those doors, but if one is and you missed it, the only way to get them is to restart.
It unlocked for me on my 4th hat creation. The backwards green ball cap hat; 3rd over from the bottom (Crocodile/Alligator hat, I think it was?)
For getting all achievements, there is no point. A true completionist I guess would want to get them all, but there is no steam achievement for it.