Geoffrey Chaucer was born into the growing English middle class, in London, most likely in 1343. His father was a prosperous wine merchant, and in the normal course of things Chaucer might have been expected to follow a similar life. But while still a young teenager he was sent to work as a page in the household of Lionel of Antwerp, son of the current king, Edward III, and brother of John of Gaunt. Thus began his distinguished service, which would last for the rest of his life, to the ruling English nobility. Much of what we know of his life comes from the governmental record. He served in positions of increasing responsibility until, as a young man, he was a trusted diplomat carrying out foreign missions of considerable importance and sensitivity. He married a woman, Philippa, who belonged to the household of Edward's queen. Everything in the record suggests that he was highly esteemed by his royal employers. He was the recipient of a succession of grants and annuities, which, upon the succession of a new king, were always confirmed.
When I think of what is known of his life, and put it next to what I know of his poetry, I think of Chekhov, the son of a serf who went to medical school and worked as a doctor while writing some of the best stories and plays of the 19th century. Chaucer started higher, and crossed a boundary higher up the stratum, but the circumstances of their lives made both men intimate with a wide range of humanity. One may detect in Chekhov's fictions the bedside manner of a good physician--intelligent, sympathetic, but sufficiently detached to guard against false judgments; and in Chaucer very similar qualities of mind and character might be associated with the sensibility of an accomplished diplomat.
His two greatest works are Troilus and Criseide, a narrative poem of some 8000 lines that he completed in about 1385, and the Canterbury Tales, the composition of which seems to have consumed his leisure time beginning in about 1386 until 1400, when he died. The completed portion reveals a plan to compose well over a hundred tales--two for each of the 29 pilgrims on the way to Canterbury and two more for each of them on the return trip to London. We have 22 completed tales and two unfinished fragments. If we work out the ratio of finished to projected, it comes to only about one-fifth, but the universal judgment has been that in the Canterbury Tales "there is God's plenty."
Some day I will read the Troilus, which is often regarded as a forerunner of the modern psychological novel. Now, Chaucer obviously did not think of himself as a medieval writer endeavoring to give us a foretaste of modern masterpieces. Nevertheless one recognizes why it's tempting to say such arguably silly stuff. For example, in the Canterbury Tales, the Pardoner, a lost soul who is aware of his own depravity, will put some readers in mind of Dostoevski's anti-heroes. But there is in Chaucer no hand-waving; the almost unbearably affecting portrait of a villain is achieved by means of a detached restraint that I tried to suggest by invoking Chekhov. Here is E. Talbot Donaldson doing a better job of it in a single sentence:
He understands both the high and the low, but he remains curiously detached from both, and it is detachment, perfectly balanced in his poetry by sympathy, which distinguishes Chaucer's art.
And the Pardoner is just one of 29 pilgrims. Even in its one-fifth finished form, the Canterbury Tales stand as a sprawling human comedy wherein all stations and aspects of life receive vivid, entertaining treatment. Donaldson, again, on the characterization of one of the Pardoner's 28 fellows, the Prioress:
Chaucer shows us clearly her inability to be what she professes to be, a nun; shows also the inadequacy of what she thinks a nun ought to be, a lady; and shows the great human charm of what she is, a woman.
So we have the Pardoner and the Prioress. I've written recently about Chaucer and the fabliau, here. Kittredge, one of the great Chaucerians, was the first to point out that a series of tales--most memorably those of the Wife of Bath, the Clerk, and the Franklin--form a "marriage group" in which pilgrims advance, criticize, and rebut, by the stories they tell, each others' views on proper matrimonial relations. As free-standing fictions, the individual tales are brilliant, but in their relation to teller and auditor they also build up the gallery of complex psychological characters. In his artistic powers and many-minded mastery of the whole human scene, Chaucer reminds us of the only English poet greater than he. Kittredge, at one point pausing in his explication, says that here is an instance of Chaucer "touching the garment of Shakespeare": it's hard to remember the particular occasion.