My awkward title comes from the fact that The Hobbit is one of those special books I've read over and over again since first encountering it as a college freshman. I read a lot, but through the years only a relatively small number of books have been significant enough to me that I have read them many times, and hope to continue reading them again and again as long as I am able. Along with The Hobbit and Tolkien's Lord of the Rings trilogy, a few other titles in this select group include Dante's Commedia, Joyce's A Portrait of the Artist as a Young Man, Augustine's Confessions, the Narnia books of C.S. Lewis, the works of Saint Patrick, and of course the Bible.
Why The Hobbit, and why do I suspect that it would appear on the re-read list of many other readers? I thought about that the past few days as I prepared for the release of Peter Jackson's first hobbit movie by again reading the story of Bilbo, Gandalf, the dwarves, Smaug, and the rest. I don't have a final answer for the book's appeal, though I surely felt it again. I can only mention a few factors that I find meaningful and wonder if they are part of the book's broad attraction to others.
One key factor is the clear sense of right and wrong, of good and evil, that comes through in Tolkien's writings. Even though his characters and the landscape they inhabit are fantasy, we have no trouble knowing that there is a right and a wrong in Middle Earth, that evil represents the absence of good, and that it matters greatly whether good will triumph. For someone who believes that this is true in the real world, but is so often confronted with evidence that many others do not, reading Tolkien is a refreshing encounter with another place where this fundamental point is not confused.
Another appealing factor is the sheer inventiveness of Tolkien. Anyone who has read far into his works or knows much of his biography is aware that The Hobbit only represents the beginning of his creativity. He invented orcs and hobbits and numerous fictional nations with lengthy histories and viable languages. He not only wrote The Hobbit, he illustrated it. In the academic world he had a great impact on our understanding of Beowulf. But there are many inventive writers and scholars out there, and I am not sure that this factor alone would be enough without the quality of the worlds he created.
Also greatly attractive to me is the apparent reality and goodness of the natural setting of The Hobbit. Middle Earth may not be real in a scientific sense, but Tolkien's descriptions of it feel real. What's more, the naturalness of Middle Earth comes through as a given good in his writing. When the natural world grows dark and oppressive in The Hobbit (and LOTR as well), we can be sure that some personal evil is ultimately to blame. When sentient beings are found living in harmony with the world, they are generally good, and when they are twisted by evil, they abuse the land. Elves, dwarves, and humans are never portrayed as perfect by Tolkien, but when they are living as they should, their relationships with the earth are harmonious. The Shire is one example of this, Rivendell another, and the lands of Beorn yet another in The Hobbit.
Finally, even without the more fundamental points already mentioned, Tolkien might have won me over simply by making birds so significant as heroes in his story. Eagles rescue the party when they are about to be killed by goblins and Wargs, and they appear again at a climactic point in the Battle of Five Armies. A wise thrush shows the way to open the back door into Smaug's lair, returns to reveal the dragon's vulnerable spot so that he can be slain in battle, and serves yet again as a liaison between Thorin and the ravens. The ravens themselves play a part in gathering the dwarven armies and spying for the dwarves. While the birds of The Hobbit might not mean as much to others as they do to me, I would have a soft spot for Tolkien because of them even if his writing were not great for many other reasons.
Alan Lee's image of Roäc and the Thrush