I read lots of things multiple times.
For fiction it does tend to be lots of SF. I just finished Steve Perry’s Matadora trilogy for the umteenth time, and started rereading Harry Harrison’s Stainless Steel Rat series for maybe the tenth time. I’ve probably read Glen Cook’s Black Company series or Barry Hughart’s Bridge of Birds the most.
For non-fiction, Machiavelli’s the prince stands out - 5 times for different university classes (political science major, concentrating on political philosophy) plus several times for fun.
However, the book I’ve probably read the most is the English conversation textbook *Streamline *, which I taught from for more than 7 years for 8 lessons a day. I can quote entire lessons from memory. 
Since I’m stuck here in Taiwan, where nearly all the libraries are stocked solely with Chinese books (bleargh), I’ve reread every book I’ve owned at least twice, if not more times. The ones that I’ve read the most:
All the Tolkien books I own: The Hobbit, the LOTR trilogy, the Silmarillion, and two books from the History of Middle Earth (I’ve forgotten their titles)
1984, by George Orwell
Fahrenheit 451, by Ray Bradbury
The Robot series, by Isaac Asimov (borrowed from the only library around here with decent English books)
The Book of Words series, by J. V. Jones
I can go on and on and on, but those are the ones I’ve read the most (read: they’re dog-eared and about to fall apart)
I also read every book I own more than once. The ones I have read the most have to be my Terry Pratchet books, closely followed by The Great and Secret Show, Everville and Weaveworld.
Add an extra t to the end of Pratchet please! I’m having a ‘dizzy’ day.
Non-fiction:
Cosmos by Carl Sagan. I keep it on my nightstand and read it when I can’t sleep. It’s the closest thing I have to a “bible”. I’ve probably read it 5 or 6 times over by now.
A Man on the Moon by Andrew Chaikin. The book that HBO’s From the Earth to the Moon was based on. It’s a tome, but I’ll re-read individual chapters over and over.
In Cold Blood by Truman Capote. Just the pick-me-up needed when I’m feelin’ blue.
Fiction:
Satan: His Psychotherapy and Subsequent Cure By the Unfortunate Dr. Sy Kassler, J.S.P.S. by Jeremy Levin. Gets funnier every time I read it (which is 5 or 6 times now).
The Stand by Stephen King. Seems to have made a lot of people’s lists.
Any and everything by Mark Twain.
Reference:
The Straight Dope compendia by Unca Ceece, of course, tucked into the water closet’s library.
Whoops!
Forgot to add Carl Sagan’s Contact in my fiction list.
Joining the Crowd:
The Stand Stephen King.
Joining others:
John D. McDonald’s Travis McGee series
Dick Francis stuff- multiple times, but he has so much stuff available.
Joining the realm of questionable taste (or Guilty Pleasures 101):
Red Storm Rising by Tom Clancy.
-me
The Consolation of Philosophy by Boethius.
Am I the only one who re-reads (dare I say it?) mysteries? I have read all the Dorothy Sayers mysteries uncountable times. Ditto for:
Tolkein
Narnia
Prydain
Hitchiker’s Guide
Stranger in a Strange Land
(mildly) Because it seems like a very long soap opera, and it’s not very well-written. I got tired of descriptions like, “And then they entered another village. In this village, the people dressed in wool, which differentiates them from the last village, where the people dressed in silk.” And I hate all the characters except for Egwene. They’ve gradually turned into complete jerks. Sorry. I can’t stand them.
I forgot:
Robin McKinley, especially Deerskin
The Cloister Walk, Kathleen Norris
Holy The Firm, Annie Dillard
Outlaw Cook, John Thorne
Dicey’s Song, Cynthia Voigt
I’m… um… memorising the Four Quartets. They work very well as the World’s Longest Mantra…
QUOTE]One series I’m not going to reread is The Wheel Of Time. I’d be shot first
[/QUOTE]
(mildly) Because it seems like a very long soap opera, and it’s not very well-written. I got tired of descriptions like, “And then they entered another village. In this village, the people dressed in wool, which differentiates them from the last village, where the people dressed in silk.” And I hate all the characters except for Egwene. They’ve gradually turned into complete jerks. Sorry. I can’t stand them.
I forgot:
Robin McKinley, especially Deerskin
The Cloister Walk, Kathleen Norris
Holy The Firm, Annie Dillard
Outlaw Cook, John Thorne
Dicey’s Song, Cynthia Voigt
I’m… um… memorising the Four Quartets. They work very well as the World’s Longest Mantra…
The Phantom Tollbooth, at least once every six months since I was seven. (I’m currently 19)
Catch 22, only twice, but I’ve read my favorite chapters at least ten times.
The entire Chronicles of Narnia, at least four times.
The Hobbit, six times.
I re-read a lot when I was a child, but less and less now. I guess I’m running out of time to get everything read at least once.
101 Dalmations by Dodie Smith, 21 times. Nineteen times to myself, and two times out loud to my younger brothers and sisters.
I used to read The Voyages of Doctor Doolittle by Hugh Lofting every Christmas vacation, while sucking on the candy cane I got from the official town Santa Claus after the Christmas parade. I don’t remember how many years I did that; probably five.
Everything by Lucy Maud Montgomery multiple times, especially The Blue Castle, my favorite, which I’ve probably read ten times.
All of the Travis McGee books by John D. MacDonald twice each, and all of Dick Francis prior to 1993 twice each. Many Agatha Christies twice each, but by no means all of them. Many Robert Heinleins, but not the ones in which he’s in Dirty-Old-Man mode (e.g., Glory Road). Really, I couldn’t begin to list all the books I’ve read twice. And I don’t think I listed all the ones I’ve read more than twice. Definitely, 101 Dalmations has the record, though.
I’m going to look like a total idiot here, but I’ve read the Flowers in the attic series (5 books) at least six times in my lifetime.
Also Pet Semetary by Stephen King. I have read that book about 4 times.
My favorite book would have to be The Lord of the Flies by William Golding though. I first read the book when I was 11 years old and I have read it at least once every year since.
My dog eared books are lying all over the house, most of them covered in mould from dropping them in the bathtub!
I’ve been enjoying this thread so much! And taking notes, since if there is a book beloved enough to be read multiple times, chances are I’ll at least like it once!
To answer the question – I fall into The Stand crowd. Why is this book so appealing? King himself has the answer in the forward to the unabridged version: we take the characters into our hearts and we want to visit them now and again. I really do wish he got postcards. I’d like to know how Frannie and Stu’s baby is.
Other favorite re-reads have shown up here. Lonesome Dove, by Larry McMurtry, for one. This is one of my favorite books and it always surprises me when I realize this. I’d guess I’ve read it 6 or 7 times. I cry every time SPOILER ALERT Gus dies. Every time I read it I think I understand something new about one of the characters. It’s a very sad book, though. It questions whether we ever do understand one another.
Further, I have read Midnight in the Garden of Good and Evil 10 times at least. This is the funniest, most tragic and entertaining true story ever written, in my humble estimation. I simply love it. I’ve read it so much I’m almost, but not quite, sick of it. I live to use the phrase “walking streak of sex” in casual conversation.
The first book I ever read incessantly was The World According to Garp. The very first time I read it, I was transfixed to the point of having a hard time returning to reality. (Think maybe I was an impressionable teen? LOL) Anyway, I loved it and it gave me a glimmer of the future the world held for me: I became a writer.
One funky little book that I re-read to the point of tatters is Addie Pray by Joe David Brown. The movie Paper Moon was based on it, but it’s infinitely funnier. A light read, yes, but it’s so much fun I find myself pulling it off the shelf if I’m in the hideous wasteland, the Land Without A Current Book.
Other I love and re-read frequently include To Kill a Mockingbird, Angela’s Ashes, Gone with the Wind (though not as much in adulthood), Anne of Green Gables (enjoying a resurgence as I’ve read it now to my children), Roots, Woman on the Edge of Time, Jurassic Park and Bonfire of the Vanities.
And forgive me, but I forget who mentioned Gravity’s Rainbow. It’s been impressed upon me for years by various people that this is a book I MUST read. I must. Yet I’ve tried a couple times and it fails to do anything but bore me. Am I not giving it enough of a chance? I’d say last time I only read about 50 pages and put it aside. Give me a clue why it’s so great and I would love to try it again.
I’m a slow reader, and haven’t read many books more than once (although a lot of books once). Guess I’m slow because I like to read aloud. I like the sound of the words.
Books I have read at least twice include:
Cannery Row, its sequel Sweet Thursday and Travels With Charley by John Steinbeck (plus most of his other books once); 1984, by George Orwell; Mark Twain’s Tom Sawyer and Huckleberry Finn, as well as Letters from the Earth several times; City Boy by Herman Wouk; The Best of Robert Ingersoll edited by Roger E. Greeley (so many times it’s coming apart), plus, once, the complete works of Robert G. Ingersoll in ten hardbound volumes that I actually found in the La Cañada, CA library (a surprise, because Ingersoll is deliberately “ignored” by many library systems); Unpopular Essays of Bertrand Russell; all of Robert Fulghum’s and Andy Rooney’s books many times each.
Over the years I have preferred nonfiction, but I like the fiction of Steinbeck, Clavell, Clancey and Follett, to name a few. I have never read a book by Stephen King, but, since so many Dopers seem to rate him so highly, I may start with The Stand soon.
I’m slow, but steady.
“Hello, I must be going.” --Groucho Marx
My re-reads haven’t been mentioned:
Jane Eyre
East of Eden
and the On Language series by William Safire.
Reading your lists of re-reads has made me nostalgic for many books that I read long ago. Specifically I think I’ll re-read Stranger in a Strange Land, Atlas Shrugged, and Lonesome Dove in the near future.