Transformation Of English Language

In 1066, William of Normandy conquered England, forever changing the English language. Before the conquest, English was a Germanic language full of complex grammar. After, French became the language of nobility and government.
Over the next 400 years, English absorbed thousands of French words while dramatically simplifying its grammar. By 1400, the language had transformed from Old English (which modern English speakers can't understand at all) to Middle English (which is difficult but somewhat comprehensible).
The final evolution came with the Great Vowel Shift around 1500, when pronunciation changed dramatically. By Shakespeare's time in the late 1500s, English was becoming recognizable to modern ears, though accents would have sounded strange - more like a "pirate" accent than today's speech.
Time traveling to chat with Shakespeare? You'd manage, though his accent might throw you. Meeting Chaucer in 1390? You'd struggle badly. And forget about King Alfred in 890 - you wouldn't understand a word.
[Sources: Cambridge History of the English Language, History of English (Crystal), Canterbury Tales manuscript studies]

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