The thing that made it click for me was introducing Refactoring and Unit Testing. Most of my professional programming career has been in OO Languages, but I spent most of it writing procedural code. You call a function on an instance of class X, and it called a different method on an instance of class Y. I didn't see what the big deal about interfaces was, and thought that inheritance was simply a concept of convenience, and classes were by and large a way of helping us sort and categorize the massive code. If one was masochistic enough, they could have easily go through some of my old projects and inline everything until you get to one massive class. I'm still acutely embarrassed at how bad my code was, how naive my architecture was.
It half-clicked when we went through Martin Fowler's Refactoring book, and then fully clicked when started going through and writing Unit and Fitnesse tests for our code, forcing us to refactor. Start pushing refactoring, dependency injection, and separation of the code into distinct MVC models. Either it will sink in, or their heads will explode.
If someone truly doesn't get it, maybe they aren't cut out for working on OO, but I don't think anyone from our team got completely lost, so hopefully you'll have the same luck.
