Reddit reviews Shakespeare's Words: A Glossary and Language Companion

Firstly, you have to approach the texts as works meant to be performed, so you have to imagine the expressions, actions, gestures, props, backdrops, etc. I have my students perform small sections of each scene to truly grasp that idea, and then we compare our performances to film adaptations. Secondly, to understand Shakespeare you have to attune your ear to the language, just as you would with a new hip hop artist with a unique style, which also might mean reading the glosses. I suggest first reading and analyzing "chunks" of Shakespeare through his sonnets before tackling the plays. As for the performance aspect, if you can't attend a professionally-staged Shakespeare play in your area, Looking for Richard is a film I typically show to students to introduce the magic of performing Shakespeare. It features Al Pacino and several other actors behind the scenes as they work out how to perform Richard III in Central Park. PM me if you can't find it. Finally, to answer your question about supplementary texts, as my school hasn't purchased access to the OED, I use Shakespeare's Words: A Glossary and Language more than anything.

David and Ben Crystal's book on Shakespeare is a thorough but accessible introduction to his language.

Though in my opinion Shakespeare's use of rhetoric is more important to understanding his craft than the nitty gritty of Early modern spelling. I'd check out Mark Forsyth's The Elements of Eloquence, which is a good primer and a bloody fun read.

http://www.amazon.com/Shakespeares-Words-Glossary-Language-Companion/dp/0140291172/