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What do the shadows represent in Plato's Allegory of the Cave?
The shadows on the wall represent an illusion of reality that the people viewing the wall try to interpret without understanding the truth; that the shadows are only shadows. The viewers of the wall have never genuinely seen what the objects which cause those shadows look like. To the viewer of the wall, all of reality is represented by shadows. The allegory is a social commentary about understanding what the true nature of the world is, and how many people never see it because of the beliefs of the society they are raised in. If you had been raised in the thirteenth century your culture's world view (your cave) would have had shadows which led you to believe that the Earth was flat and that it was the center of the Universe.
When Plato speaks of being blinded by the light of the fire, or the sun upon leaving the cave; he is discussing the way in which some people will react violently when their cultural world view is challenged to the core of their fundamental belief system. Some people would rather retreat back into the cave than have to first acknowledge, then adapt to the fact that everything they knew was wrong.
The shadows represent a false vision of the truth, an illusion about reality. Because the prisoners have never seen the true objects that exist in the world, the objects which are casting those shadows, they believe the shadows are all that is. Plato represents the philosopher with the brave prisoner who climbs out of the cave to discover the real world, and who wants so badly for his fellow prisoners to know the truth, that he voluntarily climbs back into the cave to tell them. But they kill him for this because they don't want to have to change, to adapt to a higher truth. The shadows represent false ideas that people live by in this world, or materialism, or whatever, and the objects represent the pure forms that Plato speaks of in the Republic. The form of the good, the form of beauty, truth and goodness. The prisoners are so used to the false world they have come to live in, that they can't handle the truth.
If you've seen the shawshank redemption you will remember how the prisoner who gets let free at the end is so unsure of what to do with his newfound freedom, so used to life inside the prison walls, that he hangs himself. Something like this is going on analogously in Plato's Allegory of the Cave