It's been very interesting reading this thread. So many great points.
I have acted in a lot of Shakespeare's plays, and as a theater teacher, I have directed students several Shakespeare productions, as well as countless Shakespeare scenes. For what it's worth, here are my thoughts on this subject based on my experience:
English has changed so much since Elizabethan times, and SO many of the words Shakespeare uses have either changed meaning or are not used at all anymore, and some of the imagery in his poetry is SO dense that even smart, well-educated kids have a hard time understanding it. Now having "a hard time" is often a good thing in education, as that is how deeper learning frequently occurs, but if we don't approach Shakespeare's plays the right way with kids (or adults), they will end up hating them because they make them feel stupid and bored.
I teach students in grades 6 through 12, and my attempts at having 6th graders read or perform Shakespeare has been disastrous. They are simply too young. I'd say that for middle school kids, SEEING a Shakespeare play done well is the only proper introduction. AFTER seeing a production, it can be valuable to then go back and analyze the text, but having young kids read a Shakespeare play that they have not yet seen performed is a waste of time, and is likely only going to turn most of them off to the Bard.
With high schoolers, you will have much more success getting them to understand and appreciate the plays on a textual level, but still, having them see the play and then read it will result in more engagement and understanding.
Shakespeare is like music in that you aren't supposed to understand every word and phrase the first time you hear/see it performed. Understanding every aspect of the plot and every single idea the characters are trying to communicate is not the point. The overall effect is the point. They are plays, and are meant to be consumed in one sitting and then thought about.
All of that said, I do think that we need to stop using phrases like "the greatest playwright in the English language." He was certainly the greatest playwright of his time, and hugely historically significant, but comparing his work to those of modern playwrights is like comparing apples and oranges, and telling kids that no playwright has ever achieved what he did over 400 years ago is not only untrue, it is basically the equivalent of telling them that non-musical theater is dead.
From my observation, Shakespeare's plays are loved not only because (many) of them are indeed great and timeless, but also because the Western world has been taught that they are "supposed" to like his plays, and therefore, when someone actually does, they receive the cognitive reward of feeling they are worthy of praise. Conversely, when someone doesn't like one of his plays, they have been trained to see that as "bad," and their intelligence and taste in storytelling subsequently inadequate. We as a society see Shakespeare as "high art" that only a select few are worthy of truly appreciating.
This is ridiculous. These plays are over 400 years old. They are written in an early form of modern English using and avalanche of words and phrases that don't exist anymore, and reference things that were common knowledge in 16th century England but which that no modern reader or audience member could possibly know about. If you add on the fact that tragedy ages WAY better than comedy, and that many of the comedies are barely comprehensible (and not even remotely funny without great actors and gimmicky staging), then it's no wonder that so many people hate Shakespeare - especially those who had it shoved down their throats as pieces of literature, when really, they were never meant to be treated as literature in the first place.
Because of this, I have to wonder: why is it that we as educators need to make kids enjoy Shakespeare? Because English colonialism treated him like the Jesus of theatre and created a religion out of his plays that was proselytized to the masses, and members of the Church of Shakespeare are still ringing doorbells, book in hand?
I think it's time for us to take him off his pedestal. Yes, we should expose our students to Shakespeare's plays (the best ones, anyway). It's part of being a well-educated person. But if we really want the next generation - and generations to follow - to appreciate the man and his work, we need to stop the bardolatry. Field trips to productions of his plays are ideal, but if that is not possible, there are TONS of great film versions of his plays out there. Theatrical productions filmed in front of a live audience are vastly preferable - National Theatre, Globe Theatre, Stratford Festival - all of these are available online for a relatively low cost.
Helen Mirren is right. Students need to SEE Shakespeare. And if we want them to like Shakespeare or at least appreciate him and his work, we need to treat and acknowledge his plays for what they are: historically significant and often still enjoyable and meaningful to watch, but not the be-all end-all of the theatre. That point of view - especially as taught to our children - is simply dangerous to the mission of keeping non-musical theatre alive in the 21st century.