What do Shakespeare's plays tell us about his view of the world?
This question likely has an infinite number of answers, as Shakespeare's plays propose a variety of different interpretations of the world. Some plays (the comedies) are more uplifting, while others (the tragedies) offer a truly gloomy world view. It helps to look at a few plays in each category to understand the different ways Shakespeare developed a philosophical expression of human existence.
In A Midsummer Night's Dream, Shakespeare creates a mystical, fanciful, comedic, and overall magical environment. His vision of Ancient Greece is populated by mischievous fairies, witless actors, and hapless lovers. It's impossible to leave a production of this play without a considerably improved attitude, as its hilarious story has a happy resolution in which all the main characters live happily ever after. All in all, in a Midsummer Night's Dream Shakespeare conceives of a dreamlike world governed by magical fairies and comedic good fortune.
The tragedies, on the other hand, present a very different worldview. King Lear, for instance, suggests that humans live in a world devoid of God or destinies. Lear often rails against the unfeeling cruelty of nature, despairing at the overall lack of meaning in life. In contrast to comedies like Dream, Lear suggests that existence is ultimately meaningless and bleak, and that humans live in a world in which happy endings are a fairy tale, rather than reality.