I have Mr. William's freshman World History class to thank for my all-consuming passion for "Three Minute Philosophy" videos on Youtube. Lucky for us, there's a video on Plato. The video describes everything from The Allegory of the Cave to Plato's views on Democracy to Plato's theory of Forms. Specifically, I think the video does a really great job of relating Plato's work with the modern world. Whereas we tend to laugh at the thought of majoring in Philosophy, Philosophers were essentially the Morgan Freemans of Ancient Greece. Meaning, everyone loved them and everyone listened to them.
I also found a rather, for lack of a better word, modern interpretation of The Allegory of The Cave. Beware, this video will either make you laugh or kill off a significant number of your brain cells. Or both. Surprisingly though, it does do a good job of visually connecting the physical interpretation of the cave to its metaphorical interpretation.