Shakespeare is an adept poet and master of the language. He layers on jokes, puns, and references everywhere. He has a massive output of work, and a number of different plots. When we compare him to other authors, it is difficult to find anyone who stacks up--but then, we're often comparing him to the wrong people.
Shakespeare didn't write books or pamphlets or epics, he wrote plays: short pieces of drama that were meant to be fast-paced and exciting. That they are mainly experienced today as bound books and not theatrical productions does not change their origins. If one wants to look at the achievements of Shakespeare, he should be compared to someone of a similar bent.
He should be compared with prolific writers known for catchy jokes and phrases. Writers who reuse old plots, making fun of their traditions. Writers of work meant to be performed. Writers who aim for the lowest common denominator, while still including the occasional high-minded political commentary. He should be compared to the writers of South Park; or the Simpsons; or MAD Magazine.
Shakespeare was meant to be lowbrow and political, but now it only reads that way to those who are well-educated enough to understand his language, reference, and the political scene of the time. If you do know the period lingo, then his plays are just as filthy
as any episode of South Park.
For example, the word 'wit' refers to a fellow's manhood (this one comes up a lot), here's an example from Much Ado About Nothing
Don Pedro: I said that thou hadst a great wit. Yay, said she, a great gross one. Nay, say I, a fine wit. Yay, said she, a fine little one. Nay, said I, a good wit. Just, said she, it hurts nobody.
Plus there's the title of that play, which references the fact that 'nothing' was slang for a woman's maidenhead, which occurs also in Hamlet:
Hamlet: That's a fair thought to lie between a maid's legs.
Ophelia: What is, my lord?
He was also not one to pass up a good cunt joke
Shakespeare often refers to mythology because that was the standard pool of reference for authors at the time. Family Guy references 1980's pop culture. Is that any less esoteric? How esoteric will Mr. T be after 400 years (assuming he doesn't find his way into the latest testament of the bible anytime soon)?
Additionally, all of Shakespeare's magnificent plots were lifted, sometimes whole cloth, from other books and histories, just like how sit coms reuse 'episode types' or borrow plots from popular movies. Shakespeare was not quite as visionary or deep as he is often given credit for. Rather, he was always so indistinct with the motives and thoughts of his characters that two critics could assign two completely different and conflicting motives, but find both equally well-supported.
Is Shylock evil because he's a Jew, evil despite the fact, or evil because of the effects of racism on him? You can make a case for all three. Marlowe (the more practised and precise writer) never left interpretation to chance, and where has it gotten him?
Shakespeare was an inspired and prolific author, and his effect on writing and talent for aphorism cannot be overstated. I think he probably wrote the King James version because it is so pretty. However, he is not the be-all and end-all of writing.
His popularity and central position in the canon comes mainly from the fact that you can write anything you like about his plays. Critics and professors don't have to scramble, or even leave their comfort zone. Shakespeare's work is opaque enough that it rejects no particular interpretation. No matter your opinions, you can find them reflected in Shakespeare; or at least, not outright refuted.
His is a grey world, and his lack of agenda leaves us pondering what he could possibly have been like as a person. His indirect approach makes his writing the perfect representation of an unsure, unjust world. No one is really right or wrong, and even if they were, there would be no way to prove it.
I don't know whether this makes him the most or least poignant of writers. Is the author's absence from the stories the most rarefied example of the craft, or is it just lighthearted pandering? Either way, he's still a clever, amusing, insightful, and helplessly dirty fellow.