I never had a strong desire to read Shakespeare (1564-1616), the only work I read in high school was Romeo and Juliet. I found him abstruse, esoteric, inaccessible and I could not appreciate his language. I thought that anyone who expressed pleasure or appreciation in reading Shakespeare was more refined than myself, or merely pretentious.
Living in England for two years, and visiting Stratford-upon-Avon, was transformative for me. Being in the home of the Bard, and experiencing the reverence he was shown in the UK, made me want to give him a second chance. During my time in England I read Henry IV Part One, Macbeth and Julius Caesar and watched the The Merchant of Venice, The Tempest and Henry V. I also read a humorous biography by Bill Bryson, "Shakespeare: The World as Stage".
More recently I finished the more critical biography "Will in the World" written by Harvard professor Stephen Greenblatt. This was an excellent resource for understanding Shakespeare, not only detailing how the events of his life shaped his writing, but also explaining hidden messages behind many of his most famous plays. Although there are great gaps in Shakespeare's life we do know where he was and what he was doing at some very specific dates and places. It is also possible to see how the spirit of the times in Elizabethan and Jacobean England influenced his works.
I do not subscribe to the theory that Shakespeare's works were ghost written by another author since we can clearly see how many of his greatest works were drawn from events in Will's own life. I agree that it is remarkable that an relatively uneducated, unrefined man from the boondocks could become the apotheosized master of the English language. However such success from obscurity to greatness could be said about many people in history: Lincoln, Napoleon, Einstein, Buffet, etc..
I could not appreciate nor understand Shakespeare in my youth. However, life's lessons and experiences have significantly improved my ability to relate to his words and enjoy them. Still, I find reading "Cliff Notes" before I tackle a piece invaluable, since the vocabulary and context of many words and phrases is concealed by the 400 years that have past since they were first recorded.