As you might have noticed quite a few of William Shakespeare's plays have made their way to my Top 100 list of Book You Must Read.
I wouldn't call myself an aficionado of Shakespeare, but I have enjoyed many of his plays and own a complete set (40 books in hardback, including sonnets and a biogprahy), which I got for steal at a used book store years ago.
My first introduction to Shakespeare was in my early teen years when my sister and I read Romeo and Juliet together. Before reading it my only knowledge of Shakespeare was that people groaned when having to read a play, so I assumed they must be terribly hard to read and understand. But somehow, perhaps having read it aloud I found it nothing like I expected and from that moment on I became a reader of Shakespeare.
Not to say they weren't at times still difficult to understand, but in spite of this I really enjoyed reading them.
One thing that did help me in my readings was watching film adaptations of the plays before reading the play. English actor and director Kenneth Brannagh made several of the plays into films and they were excellent. I've not seen all of his work, but I did enjoy Henry V, Much Ado About Nothing, and Hamlet. Of course, not all of the adaptations were... shall we say, "family friendly" and might require a little editing (i.e. DVD scene skipping), but in most cases what is skipped is semi if not completely true to the play, which might be shocking to those who don't completely grasp all that Shakespeare writes.
Another method that proved helpful was reading the plays aloud with someone else, which in my opinion is the best way for them to be read. After all, they were written to be plays! For a few years I read with my older sister and after she moved away I read them with my younger brother. I can still remember the day we opened Hamlet and I suggested he read the title role. He readily agreed... until he turned the page and another page and saw that Hamlet didn't stop talking for three pages! This was his first introduction to a soliloquy... He wasn't too happy, but pressed on. His reading, particularly aloud greatly improved and he soon became a fan of the plays as I was.
To this day on March 15, my brother will call me up and quote me several lines from Julies Caesar. It amazes me he still remember them, but every year I look forward to that call and fondly remember our time together.
If asked which is my favorite play I'd have to say for history, Henry V. For comedy, Much Ado About Nothing, and for tragedy, Macbeth. Although Richard III is also good as are Taming of the Shrew and Hamlet...
With all the attention that Shakespeare has received in the last decade I am still a little surprised at how few people have actually read a play vs. just watching a movie. If you haven't included Shakespeare on your "To Read List" you should give him a chance. If you are concerned about understanding the writing here are a couple suggestions:
1. Read aloud with a friend or family member. The more, the merrier.
2. Find an addition with foot notes, end notes, or side pages of definitions, explanations and details. There are even some editions with a "cheat" page following the original text. What I mean is page 5 might be the original play text, but page 6 is the same text translated into modern English.
3. Start with a comedy or a tragedy, these for some reason are generally easier than a history, perhaps because of the entertainment level, but don't skip the history entirely, they are excellent too.
4. Find a play you are interested in and see if the film adaptation is available. Be warned, not all film adaptations are excellent, so you might want to stick to some of the more famous plays. The movies I mentioned above are pretty good.