I was in my hometown over the holidays and heard some teachers at a table near where my wife and I were eating breakfast. One of them was discussing choosing reading assignments for a charter school they were starting. They asked for recommendations from the table of what they enjoyed while in High School. Suggestions went around the table with some popular hits (Gaiman, Prachett, Tolkien, Adams, etc) and some classics (Steinbeck, Austen, Shakespeare, etc).

The teacher responded to the former suggestions by stating "Those are all good books but I can't teach them. Those are books the kids will read without me introducing them in class." As someone who loves reading but hated English it finally clicked.

So my question is: what books should be taught in High School (ages 15-18) that aren't books kids will pick up but will love? And what books should be recognized as modern classics?