Telling you about the great depression in Steinbeck's work is a lot different from living a few years out in the world and struggling to pay rent. Even if that's still a far cry from what actually happened 80-90 years ago. I think those are the key sensations that are missing that made me resonate with a lot more classic literature post-college rather than bumbling through English class in high school.

I think you really need to spend a few years fighting your politics to really capture the politics depicted in literature. And many US grade schoolers simply don't do that.