Shakespeare's works are often considered timeless because his writing examines the human experience in such insightful and elegant ways. Shakespeare's poems and stories are woven together in such a way that people from all walks of life can relate.
As Shakespeare-Online notes, Shakespeare wrote stories in many different genres: comedy, tragedy, romance and adventure, among others. This fact alone makes his work appeal to a wide variety of people. The complexity of his leading characters and his ability to turn a phrase quite well inspires many modern storytellers to continually adapt his work for modern times.
According to Stephen Hollis, director of Farleigh Dickinson University's Theater Arts program, Shakespeare's work stands the test of time more so than other writers because Shakespeare thoroughly and repeatedly considers the question of what it means to be human without ignoring the deeply flawed nature of humanity. His stories don't just put a scenario before the audience and let it play out, but they constantly challenge the observer to think about right, wrong and how to navigate the gray areas in-between. Ultimately, Shakespeare wants to explore the question of whether people should live and allow themselves to be driven by reason or by passion.