I decided to read all of Shakespeare because of how much George loves the history plays, and to understand all the Shakespeare references in the text, and also because of this excellent post (and for other more noble reasons, but I can't lie and pretend ASOIAF isn't a big factor)
Anyway, if you like these books and want to read a Shakespeare play, here's a quick cheatsheet from my reading so far:
If you like prophecies, witches (especially Maggy the Frog), and Cersei's relationship with self-fulfilling prophecies, read Macbeth.
If you are interested in how Littlefinger's formative rejection and pain over being looked down on by virtue of his birth propelled him into creating an elaborate, tragic scheme to take down those who have wronged him, read Othello. You're gonna love Iago!!!
If you like the general ambiance of the Riverlands plot where people are running around kind of confusedly in the woods with fun banter (I'm specifically thinking of Lady Smallwood and the Brotherhood), read A Midsummer Night's Dream.
If you're interested in the lead up to Robert's Rebellion, Aerys's reign, and kingship in ASOIAF, read Richard II.
If you like when Jaime and Brienne argue with each other romantically, try Much Ado About Nothing.
If you like Arya's Braavos plotline (well, not the assassin parts, but the ambiance of Braavos) and how Jaime and Cersei pretended to be each other as children, read Twelfth Night.
If you like Dunk and Egg and want to explore the idea of a prince being raised outside of court among the common people AND/OR you like any how George deals with honor thematically, read Henry IV parts 1 & 2.
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