Milton.
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Milton.
So true. How anyone with a soul and a brain can describe Shakespeare as obsolete is beyond me. Joyce said that "Shakespeare is the happy hunting ground for all those whose minds have lost their balance" and he really is. The more I read Shakespeare the more I wonder why I bother to read anything else, so often I pick up a novel or poem and think "yes, very true, but Shakespeare has already said this, and more beautifully".
Just saw this video on Milton. Thought that others might be interested in it:
http://www.youtube.com/watch?v=OlUpe1Yblt8
Both are easy on the surface, but to get under Milton you need to really be familiar with his time, as he writes on many different levels of interpretation (deliberately).
As for who is the hardest, well, Spenser is harder than both of them. He is also neglected probably as a result, despite easily being Milton's match in terms of skill, and perhaps even influence.
I found Milton harder than both Shakespeare and Chaucer, which surprised me. I assumed Chaucer would be the most difficult.
Milton is hard to grasp in terms his many allusions and Shakespeare in terms of the many idioms he uses particular to his time period. Otherwise, they're not particularly hard to read.