1. The Commedia (Dante) – The richest picture ever painted of the metaphysical world, the pilgrim Dante is led through hell, purgatory, and paradise. At once frightening and inspiring, this medieval poem makes Dante’s journey our own, as he explores the biblical the classical, the historical, and the personal. In keeping with Dante’s literary theory, it is simultaneously literal, allegorical, moral, and anagogical. No one reading ever suffices full understanding.

2. Paradise Lost (John Milton) – Cosmic in scope, epic in form, transcendent in spirit. Combining Scripture, philosophy, and aesthetics, Milton transforms the Fall of Man into the story of Satan, God, War, Temptation, and Salvation. In my opinion, only one other literary work is as beautiful and sublime as this.

3. The Merchant of Venice (William Shakespeare)– My deep and abiding affection for the Bard restricts me to reluctantly choose only one play. Other favorites include Macbeth (my first real passionate response to literature), Othello (the tragic injustice of it all), Henry IV (the comic Falstaff and the political Hal) and Julius Caesar (the Roman way). But The Merchant of Venice possesses a complexity that tackles religion, friendship, marriage, economics, and the law all at once. I am always awakened to new ideas with each read.

4. Crime and Punishment (Fyodor Dostoevsky) – After many years of reading popular fiction, I first developed a deep respect for literature because of this book. Raskolnikov kills out of poverty, and desire, and is shrewdly hunted by the detective, Porfiry. A long game of chess occurs between the two, and Raskolnikov finds the meaning of forgiveness in the prostitute Sonya. The ultimate in existential redemption.

6. East of Eden (John Steinbeck) – A modern retelling of the Genesis story set in the post-war Salinas Valley. Adam Trask falls in love with Cathy Ames, with whom he has twin boys. Perennially unhappy, she abandons Adam and her sons, preferring life as a prostitute in a brothel. Adam endures to raise his sons with the help of his neighbor and servant, with whom he has several philosophical discussions. These discussions are deep and thoughtful, centered largely around properly teaching the boys who, unfortunately, grow up into Cain and Abel figures. The central philosophy of the novel and character motivation hinges on the Hebrew “Timshel” (“Thou Mayest”).

7. 1984 (George Orwell) – A political prognostication of the dangers of socialism and totalitarianism, Orwell’s tale of Winston’s awakening is as true as it is horrifying. All language, meaning, and value are reversed. We know what is wrong with the world, and yet we ignore it, and retrain our minds not to acknowledge it. Winston rebels, however subtly; his time spent in the Ministry of Love is appalling and gruesome, made worse by his ultimate escape from it. 1984 makes up everything that is sickeningly “Orwellian.”

8. Le Morte D’arthur (Sir Thomas Malory) – This fifteenth-century tale has remained the definitive text of Arthuriana for the last five hundred years. Covering his career from birth to death, all the major aspects of the legend are here: the Lancelot-Guinevere affair, the Holy Grail, and, of course, Arthur’s passage to Avalon. A fitting story for the end of Arthur and the end of the Middle Ages.

9. The Symposium (Plato) – The definitive voice on Truth, Goodness, and Beauty, Plato shows through a short, but infinitely complex Socratic dialogue what is the genuine nature of Love. At once humorous, tragic, and profound, Socrates reveals through logic what Love looks like, and through the missteps of his fellows and the dissipation of Alcibiades reveals what it is not. The true expression of Love, Plato argues, will order our spirits, our lives, and society as well.

10. I’m always on the lookout for more, so send your recommendations.