I may have to do this in segments, but…
First pick? The annotated Milton’s Paradise Lost.
Mine would be:
Complete works of George Orwell
Invisible Man - Ralph Ellison
It - Stephen King
Complete works of Dickens
Complete works of Shakespeare
Money - Martin Amis
Confederacy of Dunces - John Kennedy Toole
Don Quixote - Cervantes
Homicide: A Year on the Killing Streets - David Simon
Encyclopedia Britannica
I’m going to be pedantic again…* in a single volume?*
Ok, I think I’d chose a few Stephen King or Tom Clancy novels since they average like 2,487 pages each and I don’t wanna be bored!.
- re read “The Stand” for the 4th time
- “IT” for the 3rd time, but might creep me out too much reading it alone!
- “Hunt for Red October”
- “Patriot Games”
- “The Ultimate Hitchikers guide to the Galaxy” 'cuz I’d need a chuckle after reading the above 4. (It has ALL of the series in one book.)
- “World War Z”
- “War and Peace” . Never read it…always wanted to.
- “The Lord of the Rings”
- “The Hobbit”
- Vonnegut’s “Breakfast of Champions”
Not to mention the Encyclopedia Britannica.
I worked on finding single volume books for my original list. But if multi-volume series are allowed:
The Complete Idiot’s Guide series
The Encyclopedia Britannica
Everyman’s Library Contemporary Classics Set
the complete For Dummies series
Great Books of the Western World
The Harvard Classics
The Library of America Collection
The Penguin Classics Library Complete Collection
The Story of Civilization
The Year’s Best Science Fiction
Last me a winter? Heck, this would last me a few decades.
I believe he rule is multiple books…if bound in a single volume.
edited to add: I need to borrow a few million dollars. I’ve got this great idea of putting the entire Library of Congress into a ten-volume set.
That’s the rule I followed in my original list.
Ah but that is three books (or is it just one) 
And I would include those. I have read through them twice and I am sure I will read through them again.
Neal Stephenson’s last two books (Anathem and Reamde), over 1000 pages each, ought to do me for nine months. Add LOTR (3 books), William Gibson’s Bigend books (3 more) and maybe Cryptonomicon and Necromancer and I will be happy.
Got it on my Kindle 
I admit, imagining a print version may require a little suspension of disbelief, but I know it exists in theory, and that’s good enough for me
But if it’s not allowed I’d replace it with Midnight’s Children by Salman Rushdie.