Teaching The Classics

I've often wondered about the necessity of teaching the classics like Othello in the modern classroom. For many of my students, the strangely constructed sentences and healthy vocabulary of William Shakespeare can seem too challenging. But I am confident that teaching plays like Othello have a place in the modern classroom because of the emotional connection possible between the reader and the text. The only question is, how do we make Shakespear accessible to today's students.
For Othello, I assigned nightly readings. The next day, we would quickly summarize and then discuss the characters, their emotions, their thoughts, their decisions. I tried to relate the jealousy, the lack of confidence, the importance of reputation, and the idea that not all is what it seems to their experiences. Most students have something to say about those themes once they can understand the events of the play. My struggle is getting them to that point.
We are currently reading The Tempest. For this play, we are reading it in class with appointed readers and one appointed translator. Sparknotes has a fun modern translation in their No Fear Shakespeare editions.
But this method has issues as well. One is that not all readers are fluent. This makes the reading lengthy and difficult to follow.
Well, that is not what I was going to post about, but the following three quotes are. In a recent essay, my students were attempting to write a reader response showing how Othello meets certain criteria for being great literature. The criteria was that the literature should create a healthy confusion of pleasure and disquietude in the reader. Here are three interesting thoughts:
"...the characters bring pleasure to each other."
"This book was a play that was hard to follow, but a book you had to understand to get all of the critical thinking." HUH?
"In order to insure that he got Othello back..."