1984 by George Orwell.
Who didn't see that one coming. I'd talk more about it, but I'm going to use this title again for this challenge where I will go into why it is important to me. For now you will have to settle for this...
It's a dystopian novel set in the future (?) where an authoritarian government under the personality cult of "Big Brother" has taken control. Adapted by George Orwell from a similar novel We by Yevgeny Zamyatin (it's not as good as 1984), the story takes us into the life of Winston Smith, a silent resistor of Big Brother. Winston and his rebel love interest Julia, eventually join a group bent on the destruction of Big Brother and....well, if I tell you anymore, the excitement will be lost.
Did I mention this was a dystopian novel? It's not a pleasant read, but for it's time and in certain ways for our time, it's an important book. Which is why I have read it over three times. I'm not going to tell you how many times I've actually read it, but I'll tell you this: My test for whether or not I'd read particular books of the bible enough times (think Lamentations or Leviticus or Numbers) was by comparing the number of times I'd read them with the number of times I've read 1984. Yes, that's a little depressing to admit, but since you ought to know that the Bible is the most important book in my life, you now know how important 1984 is to me as well.
I was a little annoyed though that there wasn't a second runner up. I don't re-read enough. C.S. Lewis would be ashamed. There are books I've read twice, but not three and over. It's really just The Bible and 1984. I guess this is something I'll have to work on then.
What books have you read more than three times?