The Great Gatsby is the one that comes to my mind. How exactly is a modern high school student supposed to relate to any of the characters in this book? Even wh

The Great Gatsby is the one that comes to my mind. How exactly is a modern high school student supposed to relate to any of the characters in this book? Even when I was reading it in school I kept stopping and questioning just what these characters even were. It felt like reading about aliens, totally disconnected from reality. I not only lacked the historical context, I didn't have enough social context to grasp the character motivations or actions. The whole book was like the allegory of the cave. Steinbeck is a close second, though. I had to read three of the man's books (The Pearl, Of Mice and Men, and Grapes of Wrath) and I don't think I enjoyed a single page of it. I remember finding a copy of The Pearl as an adult and being shocked it was less than 100 pages. We somehow extracted 18 weeks of discussion and essays and tests on that book. No wonder I hated it. We tortured every word of it.