Crack The Book: A Beginner's Guide to Reading the Great Books

Cheryl Drury
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Confused by Confucius? Daunted by Dante? Shook by Shakespeare? I get it! I'm Cheryl, a reader exploring the world's most influential books one episode at a time. I don't do lectures, and I can't do jargon. But we do have friendly conversations about why (and whether) these books still matter. Each episode, we tackle a great book or two—The Divine Comedy, The Canterbury Tales, The Odyssey, The Prince—unpacking the big ideas, memorable moments, and surprising ways these stories connect to life today. If you've ever thought "I should read that" but didn't know where to start, you're in the right place. Subscribe to Crack the Book. Let's find out what's inside.

  1. 3 DAYS AGO

    Learning to Fly. Week 25 (1): Dante's Divine Comedy, Purgatorio

    My very dear friend Lisa Beerman joins me for this episode, and we talk all things Purgatory. Since we share a deep love for this book of the Divine Comedy she's our perfect companion for this part of the journey. We have a wide ranging conversation about translations, "ways in" to the Comedy, and the usefulness of Dante in everyday life. I hope you enjoy this conversation! Links to a few of the resources we discussed are below. We left Dante and Virgil climbing down Lucifer’s frozen body—and suddenly what was down is now up. They emerge at the base of Mt. Purgatory and climb past shades until reaching its gates in Canto 9, just a quarter of the way into the book. From there, the journey ascends through purgation, penance, and eventual joy. At the summit, Virgil departs, and Beatrice steps in as Dante’s new guide, leading him into the spheres of Paradise and toward the Highest Heaven. Reading Purgatory quickly has given me a fresh perspective. Unlike Hell’s hostility, the shades here are eager to talk with Dante, sometimes asking for prayers, sometimes simply glad to meet him. Light is everywhere—Dante’s shadow a reminder of the sun, not the flames of Hell. Each sin is purged through fitting penance: the proud bowed low under heavy stones, the slothful running ceaselessly, each step of the mountain carved with examples of virtue--carvings that move! One highlight: the poet Statius meeting Virgil through Dante’s introduction. One heartbreak: Virgil’s final farewell. If you missed the first episode about the Divine Comedy, check out "Week 24" for a discussion of Inferno and Dante's Nuovo Vitae. Next week we finish in Paradise with another guest and Crack-the-Book frequent flyer, my son Jack! This is a year-long reading list from Ted Gioia and his Honest Broker Substack. This is Part 1 of Week 25. LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) Robin Fitzpatrick's Divine Comedy translation 100 Days of Dante CONNECT The complete list of Crack the Book Episodes: https://cheryldrury.substack.com/p/crack-the-book-start-here?r=u3t2r To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    32 min

  2. 2 SEPT

    Brothers in Arms. Week 24: The Divine Comedy, Inferno

    This week it’s Dante, and it will be amazing. Full stop. Of all the classics you could read, The Divine Comedy may be one of the most intimidating, but it’s also one of the most necessary. In this episode I’ll break it down and share how to make the journey approachable. You can do this. We begin with Dante’s early autobiographical work, the Nuovo Vitae (“New Life”), a short book of prose and poetry reflecting on his youth and his great love, Beatrice. It’s tender, romantic, and surprisingly fun, especially because Dante explains his own poems. For me, it echoed Boethius’s Consolation of Philosophy with its mix of prose and verse, but here the focus is entirely on poetry itself. From there, we step into The Divine Comedy, starting with Inferno. This vast poem of 100 cantos (divided among Inferno, Purgatorio, and Paradiso) is written in tercets, here translated by Mark Musa into smooth iambic pentameter. His translation is highly readable and captures the poem’s rhythm without forcing rhyme. The journey begins when Dante the Pilgrim finds himself lost “halfway through the journey of our life.” Guided by Virgil, he descends through the nine circles of Hell, encountering mythological figures, historical personages, and unforgettable imagery. The punishments fit the crimes (the doctrine of *contrapasso*): the lustful are blown by winds, fortune tellers walk with twisted heads, flatterers choke forever on filth. I’ll share tips for reading Dante without getting bogged down: read quickly, jot a one-line summary of each canto, sketch a map of Hell, and above all, focus on Dante’s evolving relationship with Virgil. More than an epic, Inferno is a story of finding yourself in darkness and but not staying there—and having a friend to help you. Next to the Odyssey and the Bible, this is one of the books that merits your effort. This is a year-long challenge! Join me next week for Purgatorio. LINKS Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT The complete list of Crack the Book Episodes: https://cheryldrury.substack.com/p/crack-the-book-start-here?r=u3t2r To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    32 min

  3. 26 AUG

    The Halftime Report: What I've Learned About How to Read Classics (so far)

    This week marks the halfway point in my year-long reading project through Ted Gioia’s *Immersive Humanities* list, and instead of turning to Dante just yet, I’m stopping to take stock. Call it my “halftime report.” When Gioia built his list, he gave himself some rules: keep each week under 250 pages, make it global not just Western, mix in art and music, and move (mostly) in chronological order. I’ve tried to follow his structure, but I’ve also set some rules of my own: stick to the weekly schedule, read hard copies whenever possible, take notes faithfully, and—my personal favorite—skip the introductions until after finishing the book. These boundaries have kept me grounded and helped me push through the tough weeks. Along the way I’ve discovered a few key tools that make this project work. “Warm-ups” like short lyric poetry before longer epics have been surprisingly helpful in easing into a big text. Good translations (thank you, Penguin Classics) have been essential, while flashy but unreadable editions only get in the way. Writing in my books, flagging footnotes, and taking notes have become indispensable habits. And yes, the occasional YouTube lecture has saved me when I got stuck—no shame in that. There have been highs: falling in love with epic poetry, discovering Boethius’ *Consolation of Philosophy* with my son, and realizing Aristotle’s *Ethics* was hard but worth it. There have also been lows: weeks that felt too open-ended, a disappointing second half of *Confessions*, and the frustration of wanting more time to chase connections between authors. But even the “hate-reads” (looking at you, Mwindo Epic) have taught me something: knowing why you dislike a book can be as valuable as knowing why you love one. Most of all, I’ve learned that this project has changed how I read. I’m less afraid of poetry, drama, or “hard books.” I’ve discovered that reading fast has its place, that writing alongside an author can deepen the experience, and that I actually thrive on having a big, purposeful challenge in front of me. So here I am halfway through, still going strong, and more convinced than ever that the classics have something to offer ordinary readers like you and me. Next week we begin Dante, and I can’t wait. This is a year-long challenge! LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    32 min

  4. 19 AUG

    What is Love? Week 23: Abelard and Heloise, and Troubadour Poetry

    How is this project different than reading books in school? Well, I'm going a lot faster, but it's more than that. I reflect a little on the differences to get us started. I'm grateful that reading on my own is giving me time to reflect on goodness and Beauty-with-a-capital-B. And did this week ever deliver on the Beauty! This week’s reading was the letters of Peter Abelard and Heloise, a glimpse into one of the most famous love stories of the Middle Ages. Abelard was the leading logician in 12th-century France, at the height of his career, when he fell in love with his brilliant student, Heloise. Their secret affair led to a pregnancy, a clandestine marriage, and eventually Abelard’s castration at the hands of Heloise’s furious uncle. Abelard turned to monastic life, Heloise became an abbess, and the two carried on a remarkable correspondence that reveals their faith, intellect, and conflicted love. At first, I wasn’t sure what to make of Abelard. He begins his account by one-upping a friend: “You think you’ve got problems? Listen to mine.” In later letters, he almost calls Heloise a nag and suggests she should be grateful to be an abbess instead of burdened with children. As a wife, mom, and Christian, I found his dismissive view of marriage hard to swallow. And yet, the more I read, the more nuance emerged. Abelard gives thoughtful counsel, treats Heloise as his intellectual equal, and writes powerfully on women’s roles in Scripture. Heloise’s voice is even more compelling. She never stops loving Abelard, body and soul, and her honesty about desire and devotion is stunning. She also wrestles deeply with how to lead her convent well. Abelard pushes her toward embracing service to God, but it’s clear the struggle was harder for her than for him. Their letters touch on everything from the Rule of St. Benedict to church politics that nearly destroyed Abelard. By the end, through the testimony of Peter the Venerable, I found myself unexpectedly moved by Abelard too. To round out the week, I dipped into “Lark in the Morning: The Verses of the Troubadours,” a gorgeous collection of poetry from the same era. This little volume is truly on of the highlights of my library now, and I think everyone should own it! It offers some history as well as beautiful translations of Troubadour poetry. These voices, along with Abelard and Heloise, offer a vivid entry point into the medieval world. This is a year-long challenge! Join me next week for a halftime review of this reading project. LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    35 min

  5. 12 AUG

    The Worst Book I've Ever Read. Week 22: African Epics and Tales

    This week’s stop on Ted Gioia’s 12-Month Immersive Humanities List took me to Africa for two epics: Sundiata: An Epic of Old Mali and The Mwindo Epic. One was a pleasant surprise, the other… well, I’d like my hours back. Sundiata follows a young prince who can’t walk or talk, is exiled, then returns to save his homeland with his griot (advisor and best friend) at his side. I accidentally ordered the children’s edition, but the cut-paper illustrations were gorgeous, and the story had heart. It’s staying on my shelf. Then came Mwindo. He’s born walking and talking, survives his father’s attempts to kill him, becomes king, and… that’s basically it. No character growth, no larger themes—just the same boast repeated endlessly. The translation is a nightmare: bizarre metaphors (“the anus of a snail”), anatomical oversharing, and footnotes that explain nothing about the culture but plenty about which Swahili word was swapped for “aardvark.” Add in no glossary, no chapters, and sentences that flat-out make no sense, and you’ve got my least favorite reading week so far. If “epic” means hero’s journey, friendship, or fulfillment, Mwindo is none of the above. It’s childish, thin, and—between the scrotal elephantiasis curses and dietary warnings about bodily fluids—utterly unreadable. I’ve now read 21 weeks of world literature, and this one sits alone at the bottom. So unless you’re collecting nightmare translations or snail-anus similes, skip Mwindo. I’ll be spending my reclaimed time with Euripides, Chaucer, or Virgil—where the metaphors may be strange, but at least they make sense. This is a year-long challenge! Join me next week for WHATEVER IS NEXT LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    28 min

  6. 5 AUG

    From Canterbury to Camelot. Week 21: Canterbury Tales and Le Morte D'Arthur

    This week on Crack the Book, we take a big leap forward—from Augustine’s Confessions in the ancient world to 14th-century England—with selections from Geoffrey Chaucer’s The Canterbury Tales and Thomas Malory’s Le Morte D’Arthur. No translation was needed, technically, but the Middle English still felt like a new language. Both were new to me, which now feels shocking—how did I miss even a snippet of Chaucer or Arthur in school? Ted’s excerpts kept our reading manageable at about 250 pages total, but I’m glad I didn’t have to choose between them. The shift from Greece and Rome to medieval England was disorienting: the worldview feels earthier, even more “pagan” in spirit, with a Christian overlay steeped in legend. In The Canterbury Tales (Prologue, Knight’s Tale, Miller’s Tale, Wife of Bath’s Tale), Chaucer’s mastery of distinct voices shone. The Knight’s romantic chivalry contrasted with the Miller’s bawdy humor and the Wife of Bath’s abrasive self-portrait—the first woman narrator we’ve met so far. These tales, rich in character and social observation, left me curious about the medieval English church, its distance from Rome, and the lived faith of ordinary people. Le Morte D’Arthur surprised me by being harder to read than Chaucer’s verse. Malory’s prison-penned prose follows the Holy Grail quests of Galahad, Perceval, and Launcelot, where success hinges on chastity, humility, and freedom from sin. The Christian themes were far stronger than I expected, yet still tangled in a world of knightly pride and mortal failings. Galahad’s virtue is his power; Launcelot’s moral struggles bring defeat. This week left me wanting more—more Chaucer, more Arthur, and much more medieval English history. The period feels misty, almost secretive, and I’d like to learn what was happening between Rome’s fall and England’s flowering. Ted’s pick, Beethoven’s late string quartets, proved a thoughtful companion, deserving focused listening in its own right. LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram (check out the Tintagel post!) - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    36 min

  7. 29 JULY

    TMI, Dude. Week 20: The Confessions of St. Augustine

    What happens when a brilliant young skeptic is prayed into faith by his mother? This week I finished Confessionsby St. Augustine. It wasn’t all smooth sailing, but the first nine books were a revelation. Written around 400 A.D., Confessions traces Augustine’s path from pagan philosopher to Christian convert. His story is deeply personal, full of reflection on education, desire, ambition, and the slow turning of a heart toward God. Highlights from the reading: Augustine’s mother, Monica, is a quiet force of grace and persistence. She’s a moving example of faithful motherhood.His critiques of education—especially content that stirs up harmful desires—feel surprisingly modern.He’s hard on his parents, who overlooked his vices in favor of worldly success. Food for thought for sure!His conversion, sparked by Bishop Ambrose and a reading of Romans 13, is profoundly moving.The book overflows with Scripture, especially the Psalms, and includes beautiful reflections—like comparing his misuse of gifts to the prodigal son. The final chapters shift into dense theology and left me missing the warmth of the earlier story. Still, the first nine books are extraordinary. Music this week: Bach’s St. Matthew Passion—challenging, but deeply beautiful. LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    30 min

  8. 22 JULY

    What's Yours to Carry? Week 19: The Bhagavad Gita and the Rule of St. Benedict

    This week I’m considering two spiritual classics from very different traditions: the Bhagavad Gita and the Rule of St. Benedict—well, sort of. Due to a packing mishap and a limited bookstore selection, I ended up reading Benedict’s Way, a modern commentary that includes excerpts from the Rule, rather than the Rule itself. Not ideal, but still worthwhile. I also tried a technique I’ve used before: reading both texts in tandem, switching back and forth every few sections. The hope was to let the texts “talk” to each other. While the Gita turned out to be far more cohesive than I expected, the method still worked; it helped me reflect more deeply and spot some surprising resonances. The Bhagavad Gita, a Hindu sacred text, is a dialog between Krishna and the warrior Arjuna, who is paralyzed by moral doubt on the battlefield. Krishna urges him to act according to his dharma—his essential nature and duty—without attachment to outcomes. It’s a powerful reflection on purpose, identity, and spiritual freedom. And despite some troubling implications about who gets access to enlightenment, it’s my favorite of all the Eastern texts so far. Meanwhile, Benedict’s Way offered a glimpse into monastic—and any kind of communal— life centered on humility, community, and attentiveness to God and neighbor. It’s full of practical, humane wisdom, from leadership advice to a firm stance on not grumbling. Together, these texts suggest that joy, discipline, and love of the divine aren’t exclusive to one tradition. And both offer something compelling for modern life. This is a year-long reading project! Next week: Augustine’s Confessions. (Spoiler: it’s so good.) LINK Ted Gioia/The Honest Broker’s 12-Month Immersive Humanities Course (paywalled!) My Amazon Book List (NOT an affiliate link) Interview with Jonathan Haidt and Jordan Peterson CONNECT To read more of my writing, visit my Substack -  https://www.cheryldrury.substack.com. Follow me on Instagram - https://www.instagram.com/cldrury/  LISTEN Spotify - https://open.spotify.com/show/5GpySInw1e8IqNQvXow7Lv?si=9ebd5508daa245bd Apple Podcasts - https://podcasts.apple.com/us/podcast/crack-the-book/id1749793321  Captivate - https://crackthebook.captivate.fm

    34 min
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About

Confused by Confucius? Daunted by Dante? Shook by Shakespeare? I get it! I'm Cheryl, a reader exploring the world's most influential books one episode at a time. I don't do lectures, and I can't do jargon. But we do have friendly conversations about why (and whether) these books still matter. Each episode, we tackle a great book or two—The Divine Comedy, The Canterbury Tales, The Odyssey, The Prince—unpacking the big ideas, memorable moments, and surprising ways these stories connect to life today. If you've ever thought "I should read that" but didn't know where to start, you're in the right place. Subscribe to Crack the Book. Let's find out what's inside.

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