As a teacher, I have had students ask me what the best book is I have ever read. Others--those so deluded they think I must know something--ask me simply what the very best book is. I sometimes take the easy route and tell them Ezra Pound writes that the very greatest work of literature is The Iliad, a poem unmatched for its depiction of movement, beauty and human heroism. (I also suspect it jibes with Pound's theory of history to place the very best work in the dawn of western civilization and, like Nestor, to see everything which follows as being less than what was created in the golden age.) Now, while I can read Koine Greek, my Homeric Greek is so poor I cannot hack my way through Homer without the heavy use of a dictionary, and thus I have read The Iliad only in translation, and as brilliant as the translations are, I have to confess I cannot be as moved by the blow by blow descriptions of battle in front of the high towers of Troy as Pound was. Language stands in the way of my full appreciation.
Among the great books I can read in its original language is The Divine Comedy, and Dante's grand verse narrative would be my nomination for greatest book of all time. Like all interesting works, it is the product of a man born between eras and is many ways a monument to the Middle Ages at the moment they are coming to an end. No other book that I know of presents so many varieties of humanity and no other dares to judge the world as severely as Dante does. I say Dante judges because though he is traveling through the three layers of the afterlife God has fashioned, what we see is clearly seen through his eyes, and the residents of hell, purgatory and heaven are assigned the fates Dante thinks they deserve. The poem is his final word upon the world he has known before it passes away, and like everything doomed to die, his world is full of tears. I am a little disappointed he stocks the ninth cycle of hell with traitors (Is disloyalty to a nation really the worst a human can do? Only a man who has only lived within weak city-states could be so patriotic.) and I wish his meeting with his beloved in paradise were nearly as moving as the suffering he has witnessed down below. But then even a great poet will understand more of depravity and of the suffering and remorse human frailty creates than he will of divine serenity.
A second book I would mention is the collected poems of Catullus, who in fact wrote of the universe of private thought more than fifteen centuries before Shakespeare. (Dr. Bloom in his book upon Shakespeare avers the Bard of Avon created the private universe; I do not claim Catullus invented this sphere, but I will claim that people have been writing of the private human world for as long as they have been writing. Shakespeare merely wrote upon the matter extremely well.) Catullus lives in a time when it was unseemly for a man to express romantic love for a woman, especially for an unobtainable, underserving woman like Catullus' "Lesbia," so the troubled Roman invents a language to express what he is feeling, and the results are moving--though extremely painful--to behold.
To salve any pain Catullus inflicts, I would advise a reader to turn to P.G. Wodehouse, a writer I will speak of tomorrow when I continue on this subject of great books.