Again, getting inspired by some podcasting... yesterday, Bookrageous considered the desert island game with books. As in, "If you were stranded on a desert island, what 5 books would you take with you?"
To my mind there are 4 approaches to this question: the 5 books you would want to take to help you survive; the 5 books that would be best read in the middle of nowhere/a tropical locale; the 5 books you would want with you if you were going to be bored for an indefinite amount of time; or the 5 books that you could reread indefinitely.
I'm going to tackle the last 2, mostly because I'm not that into books about survival or tropical settings. So first, books I would want to read if I was going to be bored for an indefinite amount of time:
Anna Karenina by Leo Tolstoy: This is a freakin' long book that I've always wanted to read and just have never gotten around to. With indefinite time, I could not only finally read this masterwork, but also could analyze the crap out of it, preparing me to rock the face off of any literature professor I should encounter
The Rise and Fall of the Third Reich by William Shirer: I am very, very sllloooowwwllyy getting through this book right now. It's literally one of the most fascinating books I've ever read and I take something away from it everytime I read a chapter. The problem is that it's about 1200 pages of deep thinking, meaning that I can only sip, not slurp. If I had a lot of time, I could read a chapter a day and actually get through it at a reasonable pace.
The Most of P.G. Wodehouse by P.G. Wodehouse: If I'm stranded somewhere, I'm going to need a laugh now and again. This collection of Wodehouse short stories is always a guaranteed way to make me giggle. It's another one that I never seem to be able to finish, but I could read and reread for a long time and still derive pleasure
The Brother Karamazov by Fyodor Dostoevsky: See Anna Karenina... this is another long book that I really want to have read but never seem to get momentum on
Masterpieces in Miniature by Agatha Christie: This is my favorite short story collection from one of my favorite authors. If I just need a flavor burst of intrigue and enjoyment, I often turn to this for a quick story. Perfect for long term boredom mitigation.
And books that I could reread indefinitely:
Jane Eyre by Charlotte Bronte: This book changed my understanding of what fiction can do and how it can talk about big ideas. Aside from pure plot enjoyment, it's a book that makes me feel and think deeply.
The Bible: Kind of obvious, yes, but it's just ideal for indefinitely reread - deep ideas, very long, and practical for coping strategies.
Harry Potter and the Deathly Hallows by J.K. Rowling: It's my favorite book in one of my favorite series and it's all about perseverance through difficult times. Apropos, oui?
The Chronicles of Narnia by C.S. Lewis: Specifically, I'm talking about the gorgeous collected edition of all the books into a single volume with the beautiful original color illustrations (this is what I gave each of my nieces as the day of birth present). I have these on audio and already "reread" them at least twice a year. I don't get tired of them. I don't cease to be moved and changed by them. And I certainly wouldn't want to be stranded without them.
Remains of the Day by Kazuo Ishiguro: I just love this book - it's a downer, so maybe not the best for a dire situation? But I don't care. I love this story and the main character just breaks my heart. I love him so, and I get so involved with what's happening to him every time I reread.
What are your "desert island" picks? Is there another way to look at the question?