Well, Veeky Forums?
>1) He's been done to death.
There is so much other great theater out there. Sure, it's not free to produce. Sure, it's not as familiar. But we're going on 500 years of ubiquitous Shakespeare. I don't think papal indulgences, Aztec virgin sacrifices or burning witches at the stake lasted as long. Remember, every time you produce Shakespeare it means you're preventing your audience from appreciating a different writer. Recall the master's own words, “I wasted time, and now doth time waste me.”
>2) Someone else has already thought of it–and probably did it better.
Richard III in Nazi Germany. Hamlet (or Macbeth) in the Nixon White House. Othello as an Uncle Tom yes-man killing other dark-skinned people for the white man and constantly berated by a black-power Iago who spouts Malcolm X and Eldridge Cleaver. Conceptualizing, updating and generally fucking with Shakespeare is fine. But whether your idea takes place in outer space, the old West or a rectory, it's probably already been done. So why bother? Commit the oldest sins the newest kind of ways.
>3) He's wordy.
Shakespeare never heard–or at least never heeded–the adage that less is more. His plays are filled with unnecessary characters, scenes, jokes and rambling speeches. Case in point: the ridiculously convoluted monologue in Henry V,in which a doddering archbishop rambles about the ancient history and geography of France, is some 60 lines long–nearly twice as long as Hamlet's “to be or not to be” monologue. Shakespeare makes David Foster Wallace read like Confucius; if he'd written the begats the Bible would be a 10-volume set. It takes a long time to read him, but even longer to sit through.
>4) You don't have the meat.
The greatest Shakespeare plays I've seen locally have either featured fantastic ensemble performances (Mark Rucker's Taming of the Shrewat SCR) or towering individual performances (Ron Campbell in Shakespeare Orange County's Richard III, and the Laguna Playhouse's Othello). For the most part, however, inept actors who neither understand nor are able to deliver the words plague most local productions. Unless you have a cast, from top to bottom, that is skilled enough to speak the speech, don't waste my fucking time. “It is not enough to speak,” Shakespeare wrote, “but to speak true.”
>5) He really isn't that good.
It's not just that everyone knows how his plays will end (Romeo kills himself, Hamlet gets stabbed, Othello chokes the white broad). It's also that he stole most of his plots, created so many unnecessary characters, and, if you take away the dick jokes and not-so-veiled homoerotica, really wasn't that funny. And even those who proclaim him an architect of the English language don't realize that a lot of the phrases he's credited with creating–all that glitters is not gold, it's Greek to me–were hackneyed in his day. “Oh, what fools these mortals be.”