First, I can't recommend an edition because I'm unable to read Shakespeare and understand it. I don't try anymore. I just go to the plays and let the actors/director do the work of interpretation for me.
Some of the plays that I like the best are the ones that everyone else hates. I think Troilus and Cressida is the ultimate date play because Cressida vows eternal love and then transfers her affections when expedient. Coriolanus is good for your Ph.D. friends because the main character is so very like the average academic (Coriolanus is a patrician who can't believe how useless the average plebian is and isn't shy about saying so; he runs for political office but is eventually hounded from Rome because he is unwilling to pander to popular taste). Timon of Athens is great for the Age of the Microsoft Monopoly because it shows how people worship wealth and ignore character and personal quality.
N.B.: I told an MIT friend that I'd been to see Kenneth Branagh's 70mm movie version of Hamlet (done without any cuts). He asked "was it good?" I never know what to say in situations like this because I can't imagine that a binary opinion is useful. So I just said "the cinematography was great but the script was a little weak" :-)