1. "The Republic" by Plato. So much of the most profound thought in the West is a serious wrestling with issues raised by this book.
2. "The Three Sisters" by Anton Chekhov. In his great-est play, Chekhov makes deep disappointment our constant companion, yet we prevail.
3. "Beloved" by Toni Morrison. The author looks unflinchingly at the catastrophic with grace and dignity.
4. "The Prophets" by Abraham Joshua Heschel. He lays bare the roles of righteous indignation and indifference in justice.
5. "In Praise of Folly" by Erasmus. He shows how we all, particularly Christians, should try to laugh at ourselves and love others.
A classic that, upon revisiting, disappointed: The poems of Philip Larkin. He's renowned for his comic sensibility, but I found mere wit and iciness.
A book you hope parents read to their children: "The Fire Next Time" by James Baldwin. His letter to his nephew is wise advice to love and serve.