First thing that comes to mind…
A Tree Grows In Brooklyn
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The Lord of the Rings. Certainly the one I’ve reread the most, though not as much recently. (The last time I reread it I remember thinking it wasn’t the best book in the world.)
For current rereading probably A Civil Campaign by Lois McMasters Bujold. As always, both thoughtful and great characters combined with a great rom-com storyline.
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Mentioned already, but Gone with the Wind (favorite movie, too) and A Prayer for Owen Meany (I think John Irving is our greatest living author). The Cider House Rules is #3.
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I have two.
The World According to Garp
The Paper Bag Princess
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That used to be my favorite book, but the last time I read it, I thought man, this writer is so pretentious and overly wordy.
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The Abandoned by Paul Gallico
@sherpa The Paper Bag Princess is my favorite children’s book.
No way can I choose one.
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Middlesex by Jeffrey Eugenides
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The Miraculous Journey of Edward Tulane by Kate DiCamillo.
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Outlander by Diana Gabaldon
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One Hundred Years of Solitude by Gabriel Garcia Marquez
The Namesake by Jhumpa Lahiri
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The Pearl by John Steinbeck
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Michener – Texas
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I adore The Paper Bag Princess!
Persuasion
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Winnie the Pooh.
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Cry, The Beloved Country (by Alan Paton).
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A Thousand Splendid Suns.
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Another vote for Gone with the Wind. I first read it when I was in 7th grade. I checked it out of the school library on a Friday in January. Then it started snowing and snowing and snowing. We had two weeks of snow days off of school, after having been back in school for just a week or two after Christmas. It was the same time Roots was airing on TV. I spent the days in my room reading GWTW and the evenings watching Roots with my family.
Jane Eyre and To Kill a Mockingbird are tied for second. 
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I have a similar Gone With the Wind Reading experience. As a kid, I picked it up at the library on a summer day. Brought it home and read it all day into the late night. Could not put it down. I was crying at like 1 in the morning when her mother died and didn’t stop through the rest of the book. So, I basically read it in one very long sitting.
I reread it about 20 years ago as an adult for a book club. Most books I have returned to as an adult have not held up, But, Gone With The Wind did.
I also saw it in the movies as a young teen with my parents. A rare time when it was rereleased in theaters (before it was ever shown on TV). I again cried though about the last hour worth. I still never tire of watching the movie.
Note, I usually never cry at movies or when I read books, so my emotional reaction at the time was unusual for me.
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