Totally agree on Catcher. You know, I never had to read that in high school — I read it on my own, in part because my dad suggested it to me (excellent fathering moment there, heck of an example).
And yes, there is something a little more esoteric about On The Road, especially with its likeness to Jazz. I kind of think the meandering nature of it, and the music, adds to its appeal to a young boy. Or, at least it did for me. Teenage boys aren’t the most focused, and it’s cool to see an arena where there’s a freedom to indulge that kind of thinking.
Gatsby: not my favorite novel. I find it a little heavy handed. Or maybe it’s that the symbolism was beat into me by my high school teacher. I agree, it’s not the best book for teenagers to read, there’s no way for kids to empathize with it.