• The Divine Comedy - Dante Alighieri, 1472
    • There's nothing I can say about Dante's Divine Comedy that hasn't already been said a thousand times over and a thousand times again, so I just want to stress here the importance of finding a translation that works for you. It really does make all the difference. If you're reading purely for the poetry and are willing to sacrifice some of the textual integrity, Clive James is an excellent option; for a more accurate and academic approach, your best option will probably be the Hollander translation, which is available in three separate volumes with extensive notes. For an elegant balance between accuracy and poetry, I have always preferred the John Ciardi translation, who infuses the Comedy with such flair and flavor that it becomes impossible to resist. Ciardi, though, stays closer than James to Dante's original text. 
  • Sir Gawain and the Green Knight - Anonymous, 14th century
    • Sir Gawain and the Green Knight is a text which I had trouble understanding until I studied it in an academic setting; it's an absurd, confounding, anticlimatic work that can easily come across as irrelevant and self-indulgent to modern readers unfamiliar with its context. Do your research, though, and you will be rewarded. Deftly dancing through allegory and symbolism, Sir Gawain navigates the troubled waters between pagan mythology and Christian ideology in an attempt to reconcile the two through the lens of an Arthurian fable, and the result is one of the strangest and most strangely compelling pieces of literature you'll ever read. Sir Gawain never fails to amaze and entertain. 
  • The Canterbury Tales - Geoffrey Chaucer, 1478
    • The Canterbury Tales always makes me feel bad; I know that the original Middle English is the only proper way to read it, the only way to fully experience Chaucer's humor and wordplay, but I typically end up settling for a modernized translation. So I am being entirely hypocritical when I encourage readers to opt for the challenge and choose an untranslated edition. But if it's what gets you reading, a translated version is better than nothing (and perhaps it will encourage you to go untranslated once you are familiar with the text). The Canterbury Tales is full of delightfully crude humor, engaging characters, and compelling stories that span a variety of genres. Literature doesn't get much better.
  • Samson Agonistes - John Milton, 1671
    • Milton's meditation on gender, religion, disability, and mass murder, inspired by the Biblical story of Samson and Delilah, becomes chillingly relevant every time another act of terrorism is committed. Our ostensible hero, Samson, has slaughtered his enemies en masse in the name of religion, a motif which echoes uncomfortably across the years; this, though, is precisely why Samson Agonistes remains such a difficult and fascinating text. There is a lot to unpack in this relatively short closet drama. 
  • Paradise Lost - John Milton, 1667
    • I mean...it's Paradise Lost. Am I supposed to tell you that it's the greatest poem ever written in the English (heck, the greatest anything ever written in English)? Because it is. It really is. Milton's magnum opus is no doubt a challenging read, and you'll likely need an edition with proper annotations to help you along if you're reading for the first time (the Hackett Classics and Norton Critical editions are both good options), but it's entirely worth it. There are at least half a dozen sequences in Paradise Lost that rank among the best scenes in the history of literature (not that I've read everything ever written, but I think a degree of hyperbole is in order when we're discussing a book in which mountains are literally dropped on heads): the introduction of Sin and Death in Book II, Satan's monologue in Book IV, the battle in which mountains are literally dropped on heads in Book VI, Adam and Eve's discussion of suicide in Book X, and the departure from Eden in Book XII rank among my favorites.