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I wrote these suggestions to help out folks on WIG who were having trouble reading Canterbury Tales and Shakespeare. I post them here mostly for reference.

I always suggest reading original Canterbury Tales out loud in a Scottish accent. It is way less work and makes perfect sense that way. Modern Scots accents are much closer to medieval English in pronunciation than modern (post-vowel shift) Oxford or American English. As CT was spelled phonetically, it just reads faster that way.

I learned this trick while reading medieval facsimile manuscripts while getting my Masters in medieval history ages ago.

Shakespeare's generally better out loud too, but it's not as crucial. Which are you reading? Keep in mind that part of what makes shakespeare difficult for modern readers is that it's written in slang and often full of jokes. If you are having trouble, your public library may have the plays on film which can help if you just aren't getting it. They were made to be acted, not read after all.

Remember that Shakespeare needed to play as entertainment as well as art. Most of the plays start with something to grab the attention of the drunks up front. They needed dirty jokes and sword fights to keep those drunks quiet and from throwing things on stage. The plays were for everyone.

I think the Dicaprio romeo+juliet captures the feel of that rather nicely: the bawdy, the tragic, the divine, and the foolish all wrapped up together.

Not all the plays are brilliant either. (Titus Andronicus is particularly flawed, though the Anthony Hopkins/Alan Cumming movie does a wonderful job with the material). Several of the early plays like Two Men from Verona are clearly substandard too. This isn't to take away from the beauty and complexity of something like Hamlet or Winter's Tale, but I find Shakespeare is less intimidating if people remember that he was certainly just a human who learned his craft on the fly and was playing to a wide audience. Putting him up on a pedestal does no one much good and scares people off. Read lightly, laugh at the jokes, and take it as it comes.