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Chaucer is probably the earliest English poet you're likely to read. A first glance at the original Middle English of the Canterbury Tales, with all those strange-looking words, might be enough to tempt you to slam the book shut, either in disgust or in terror at having to learn it all. But take a closer look and examine some of the words. You'll see that many aren't any harder to understand than when some people, trying to be "olde"-fashioned, write shoppe instead of shop. (Chaucer's English is in fact where this idea originated.)
Try to get a dual-language edition of the Canterbury Tales, in which the Middle English original is printed on one side of the page and modern English on the other. When you've gotten some practice reading the original words and checking against the modern English, you'll find that the rhythm of Chaucer's poetry gets easier to understand.
Why is it called "Middle English"? Simply because it's at the midpoint between the ancient language spoken by the Anglo-Saxons of England and the English we speak today. In fact, you might feel grateful that you're reading Chaucer instead of the poetry of some of his fellow fourteenth- century poets, because Chaucer's dialect-the Middle English spoken in London-is the language that evolved into our English, while the dialects the other poets used died out. Imagine trying to read something written in a hillbilly drawl or in a Scottish brogue; standard English, even if it's not what we speak all the time, is easier to read.
Even if Chaucer had never written a word, it makes sense that the speech of London, the hub of English society, should develop into the standard English that eventually came over on the Mayflower. But Chaucer gave a great boost to the prestige of English, as Shakespeare did later on. It's partly because of Chaucer's terrific (though unintentional) public relations job that the poet John Dryden, three hundred years later, called him "the father of English literature."
There is a robust flavor to Chaucer's language that we can't get in a translation, no matter how good it is. You won't be able to get the nuances of all the old words. But after a while you'll almost be able to hear the pilgrims chatting away.