I have read two books more than a 100 times, for different motives and with different consequences. Hamlet I read a 100 times for my dissertation, The Inimitable Jeeves by PG Wodehouse a 100 times for comfort. The experience is distinct from all other kinds of reading. I’m calling it centireading.
I read Hamlet a 100 times because of Anthony Hopkins. He once mentioned, in an interview with Backstage magazine, that he typically reads his scripts over a 100 times, which gives him “a tremendous sense of ease and the power of confidence” over the material. I was writing a good chunk of my doctoral dissertation on Hamlet and I needed all the sense of ease and power of confidence I could muster.
It’s not necessarily the quality. The Inimitable Jeeves does not contain the best Wodehouse story. That is either Lord Emsworth and the Girl Friend, which Rudyard Kipling called “the perfect short story” or Uncle Fred Flits By collected in Young Men in Spats. But there are no dull moments in The Inimitable Jeeves, no bad parts. Each plot is a novelty, without a trace of laziness. There is not a single weak verb in the entire book.
Interesting. I wonder what my friend Hoade would have to say about this?
For me, I don't think I've read any book a hundred times, although I might be in the upper two digits for a few books.
One book I've read so many times my copy is falling apart is Hackers: Heros of the Computer Revolution. It's about three groups of iconic programmers, the MIT graduate students in the 60s (Greenblatt, Gosper, Tom Knight, etc.); the Homebrew Computer Club group from the 70s (Woz, Felsenstein, Captain Crunch, etc.), and the scores of teenagers banging out computer video games in the 80s (John Harris—all of this is from memory and I'll stop now before I post the entire book from memory). I can certainly say it had an effect on me and heavily influenced my views on programming.
Another book I've read dozens of times is Have Space Suit, Will Travel, the first science fiction book I read (so it's heavy with nostalgia), and one that doomed me to reading science fiction almost exclusively. My favorite part of the book is when Kip (the main protagonist) is imprisoned on Pluto and he spends his time figuring out how fast he travelled to Pluto by knowing both the time (five days) and distance (30 AU), while upset that he doesn't have his slipstick to help with the calculations (and I now have a few slipsticks of my own because of this book).
I'm not sure what that says about me, though.
Another book I've read uncountable times is Snow Crash, a wild science-fiction cyberpunk romp of the near future where the United States Government is just another franchise, and the main villain is a cross between H. Ross Perot and L. Ron Hubbard whose hired hand, an Aleut harpoonist, has been declared a sovereign nation unto himself (for he has his own tactical nuclear weapon).
Yes, it sounds insane describing it, but it is really good, really funny, and again, I'm not sure what it says about me that my favorite bits are the exposition-heavy bits about neurolinguistic hacking.
There aren't many other books I've read quite as often as those, but if you include comic books, then there are about a dozen or so Uncle Scrooge comic books I probably have read a hundred times or so …