50 Books to Read Before You Die

words to inspire before you expire

Page 22 of 33

Ulysses

Good morning, class.

I’m not hiding my bias here . . . this is one of my favorite novels ever. I’ve read all 700 rambling pages of James Joyce’s Ulysses twice—once with the reassurance of a college classroom, and a second time “for fun.” I’ve mentioned it in almost half of the 100+ posts I’ve written for this blog (I recommend revisiting two of them: A Portrait of the Artist as a Young Man and Modern Literature; the review might help).

But I’m in the minority here. Most people who try Ulysses find it meandering and over-complicated. Even those that do like it tend to appreciate it from a distance, for how it changed history or defined a literary movement, but they don’t like to read it. I’m in the minority because I like experiencing the scope of the story, the empathy created by the characters, the literary connections, the “everything-is-connected”-ness of the details . . . I like it for exactly what it is, and not many people would say the same.

But, students, if I can show you why it made the 50-books list at all, maybe you can see why I like Ulysses so much.


Actor Milo O’Shea as Leopold Bloom in the movie version of “Ulysses” (1967)

The story takes place in Dublin, Ireland, over the course of one day: Thursday, June 16, 1904. Leopold Bloom, our “hero,” is a Jewish advertising agent roaming the streets of Dublin, and his internal monologue narrates the story in messy fragments. His thoughts wander over (among other things) the child he lost 11 years ago, his father’s suicide, and the affair that his wife, Molly, is currently having with another man.

Meanwhile, Stephen Dedalus (protagonist of the prequel, Portrait of the Artist) deals with his mother’s recent passing, his unbearable alcoholic father, and his cynical disdain for just about EVERYTHING (he’s a little nauseating). He roams Dublin’s streets as well, and he and Bloom spend most of the day almost meeting, until they run into each other in the last few chapters like destiny—a father longing for a missing son, and a son wishing for a better father.

James Joyce, author of Ulysses (1922)

And then, without giving too much away, the novel ends by giving Molly Bloom a voice of her own—the final chapter is her epic monologue reaching beyond the confines of the single day. She rambles through cataclysmic run-on sentences on sex, love, marriage, memory, and femininity, and fondly remembers the day when she agreed to marry Leopold.


There are too many literary references to count, but the most important ones are about The Odyssey by Homer. Bloom is Odysseus, journeying from his home and back (boiling down 20 years into one day), trying to return to his “son” (Stephen/Telemachus) and his wife (Molly/Penelope). The terrifying Cyclops becomes the bigot spouting his beliefs in the bar, while the visit to the underworld becomes a funeral, and the entrancing witch Circe takes the form of a prostitute in a brothel.

These Odyssey references, where the name Ulysses comes from, give the novel it’s epic-ness. The length of this one day is impressive, so filled with detail that it overflows at the seams, and it still doesn’t capture every single moment of the day. The ancient has been updated to match advances in technology and societal evolution, but it still meets the same archetypes it’s known for.

Most importantly, Bloom is a modern Odysseus—less a warrior, more a gentle soul. He is kind to animals, has a love for science, and empathizes with Molly’s extramarital desires. Unlike most men, he knows he doesn’t own her, and that she could be suffering just as much as he is over their long-lost child. He leaves only room in his heart for compassion, making him more of a hero than anyone else in the story . . . because a modern hero isn’t someone physically strong, but rather someone who performs simple acts of kindness.

Statue of James Joyce in Dublin, Ireland

So, even though there are literary reasons why Ulysses is a masterpiece, it’s Bloom’s compassion and empathy, found throughout the novel, that make this book good. It may be hard to see under the complicated language and plot, but this novel has more love on any one page than most novels can show in a hundred. Joyce handles grief, prejudice, hope, sex, depression, death, longing, wonder, and life, all with a deep and profound love.


Sometimes, it surprises me how I’m in the minority in liking this book, and then I flip through its pages and remember—this novel is HARD to read. It’s an experience that nothing can replace, and for that reason it belongs on the list, but it is not a book you just pick up and read!

If you are going to try it, and you don’t have a literary professional standing nearby at all times, you might try reading a guidebook along with it—I recommend Ulysses and Us: The Art of Everyday Living by Declan Kiberd. It’s pretty focused on understanding the intentions behind the novel, and it helped me find the love within Ulysses. I also recommend any and all online resources—a summary won’t replace the novel, but it will help you understand what on earth is happening.

I may be a 23-year old blogger, but I think I understand Ulysses, so feel free to ask me questions after class (a.k.a. in the comments below). I absolutely didn’t cover everything here, but I’ve got plenty more to say on this subject if you want to know more. Seriously, ask me questions—all I want to do is talk about Ulysses all day.


Now that I’ve finished Ulysses, I’ve started reading Jane Eyre by Charlotte Brontë. Whenever I tell people this, they stare, like reading Ulysses and Jane Eyre outside of school isn’t normal behavior. It seems perfectly normal to me.

Anyway, I’ll see you for class next week.

Prof. Jeffrey

“I was a Flower of the mountain yes when I put the rose in my hair like the Andalusian girls used or shall I wear a red yes and how he kissed me under the Moorish wall and I thought well as well him as another and then I asked him with my eyes to ask again yes and then he asked me would I yes to say yes my mountain flower and first I put my arms around him yes and drew him down to me so he could feel my breasts all perfume yes and his heart was going like mad and yes I said yes I will Yes.”

—from Ulysses by James Joyce

“—But it’s no use, says he. Force, hatred, history, all that. That’s not life for men and women, insult and hatred. And everybody knows that it’s the very opposite of that that is really life.

—What? says Alf.

—Love, says Bloom, I mean the opposite of hatred.”

—from Ulysses by James Joyce

Off-Topic: Modern and Postmodern Literature

Hello again, class.

We’ll have a bit of a history lesson today, and talk about literary periods. Historical context can redefine a piece of literature, and something that’s always helped me with reading older texts is understanding which period of history it came from. The Victorian Era, for example, was the era of Great Britain during the reign of Queen Victoria. I know little bits about Victorian society, belief systems, social stigmas . . . each one increasing my understanding of novels and poems of the time. It’s basic reading strategy any good blog professor should know.

My two favorite periods of literature are Modernism and Postmodernism (which are more like one 2-part period, but I didn’t write the textbooks). More than being the eras of some of my favorite works, I think the majority of the books on the 50-books list could fall in the categories of modern or postmodern literature. That alone makes it worth knowing what these categories mean and how they apply to novels on the list.

(Disclaimer: I am summing up entire textbooks worth of information into a blog post. It’s a LIMITED analysis.)


Modern writer F. Scott Fitzgerald, author of “The Great Gatsby.”

Modern literature doesn’t actually mean “modern” like new or contemporary. It sort of meant that at the time, but that period is about a hundred years old by now. When people talk about modern literature, they’re usually referring to the first half of the 20th century, ending around the same time as the end of WWII. That period of history was, on a worldwide scale, sheer chaos.

Both World Wars, the Great Depression, political movements for women’s rights, the Harlem Renaissance, introduction of Freud’s theories, the roaring 20’s, advances in technology . . . these are fractions of the chaos of the time. Traditions were breaking down, becoming fragmented copies of the old world. Questions were asked about morality, society, sexuality, religion, government, the future—questions that were never considered before.

Modern Writer Ernest Hemingway, works including “The Sun Also Rises” and “The Old Man and the Sea.”

The art reflected the chaos. Novels like The Grapes of Wrath and As I Lay Dying were chaotic in the most complicated ways; they broke the rules of grammar and storytelling, and they sacrificed old traditions to make room for greater truths. Poems like T. S. Eliot’s “The Waste Land” and W. B. Yeats’ “The Second Coming” broke the rules of poetry and removed the comfort of structure.


The dates are shifty for Modernism, so they are just as shifty for the sequel, Postmodernism. Ending with WWII and working through the Cold War and the later half of the 20th century, the Postmodern Era shares a lot of similarities to Modernism. The chaos of the 50s, 60s, and onward, the continuing breakdown of traditional values, the Vietnam and Korea conflicts, the birth of nuclear power, the Civil Rights movement . . . the chaos continued.

Postmodern poet Allen Ginsberg, author of “Howl.”

But one of the key differences was how the artists responded (which is why it gets a different name in the textbooks). The artists of the modern era were more afraid of the chaos, and the art was used to help them cope with it. But postmodern artists celebrated the chaos; they relished in the collapse of the old and the strangeness of the new.

Novels like The Catcher in the RyeThe Color Purpleand On the Road fall in the postmodern category. These writers took the previous generation’s fear and apprehension and transformed it into a movement that praised the breaking of tradition. Novels like these lived into the chaos of the time.


Postmodern author Margaret Atwood, author of “The Handmaid’s Tale.”

But as I said, the reason I chose these two periods for today’s lesson is not just because they’re my favorite, but because they sum up most of the books on the 50-books list. Before the 20th Century, elements of modern and postmodern literature can be seen popping up among the best of literature. Novels like The Picture of Dorian Gray and Pride and Prejudice and even older pre-novel works like Hamlet and The Canterbury Tales have elements reflecting the chaos: the depths of psychology, the fear of advancing technology, the downfall of conventionality, the inherent wrongness in rules of morality and religion.

Personally, I think all of literature was leading toward the birth of modern works. Questions about race asked by Oroonoko and Robinson Crusoe are answered by literature from the Harlem Renaissance. The heavily structured language of the Victorian Era’s A Christmas Carol and The War of the Worlds led to the deconstruction of language in A Portrait of the Artist as a Young Man. Early women writers like Aphra Behn and Jane Austen opened the doors for modern and postmodern writers like Virginia Woolf and Alice Walker. There’s no Ulysses without Dante’s Divine Comedy.


That’s my theory, anyway. And I like it for the same reason I like Ulysses: the “everything-is-connected”-ness of it all. Granted, it’s not a very scholarly theory, but it puts the “story” in “history.”

As I finish up Ulysses, you’ll hear more of this theory—next week is the big one!

Until then, enjoy your week.

Prof. Jeffrey

“Mr Bloom glanced from his angry moustache to Mr Power’s mild face and Martin Cunningham’s eyes and beard, gravely shaking. Noisy selfwilled man. Full of his son. He is right. Something to hand on. If little Rudy had lived. See him grow up. Hear his voice in the house. Walking beside Molly in an Eton suit. My son. Me in his eyes. Strange feeling it would be.”

—from Ulysses by James Joyce

“Ineluctable modality of the visible: at least that if no more, thought through my eyes. Signatures of all things I am here to read, seaspawn and seawrack, the nearing tide, that rusty boot. Snotgreen, bluesilver, rust: coloured signs. Limits of the diaphane. But he adds: in bodies. Then he was aware of them bodies before of them coloured. How? By knocking his sconce against them, sure. Go easy. Bald he was and a millionaire, maestro di color che sanno. Limit of the diaphane in. Why in? Diaphane, adiaphane. If you can put your five fingers through it, it is a gate, if not a door. Shut your eyes and see.

Stephen closed his eyes to hear his boots crush crackling wrack and shells. You are walking through it howsomever. I am, a stride at a time. A very short space of time through very short times of space. Five, six: the nacheinander. Exactly: and that is the ineluctable modality of the audible. Open your eyes.”

—from Ulysses by James Joyce

On The Road

Welcome back, class.

Jack Kerouac’s On the Road fits nicely between two other novels I’ve read for this blog: The Grapes of Wrath and The Catcher in the Rye. Kerouac’s novel has the same nonconformist, rebellious attitude as The Catcher in the Rye (with a little less teen angst), but Catcher is all in the narrator’s head. Though just like The Grapes of WrathOn the Road has the sense of a sweeping American portrait. For its 1950s setting, it describes the entire country poetically and perceptively, which is why it makes the list.


But as good a reason as that is, I wouldn’t say On the Road was worth my time—and that’s entirely because of the story and the characters. The narrator, Sal, develops a friendship with a man named Dean Moriarty, and the story is about the many cross-country road trips they make with each other. They rarely have enough money, which never bothers them, and they find ways to enjoy the chaos of living on the open road—speeding recklessly across the landscape, sleeping around, drinking, and finding money where they can.

These two characters, with their rotating roster of friends and lovers, are always crossing the country or waiting until they can cross the country again. They can’t seem to stay in any place for long. My theory is that they are looking for happiness—something they’ve never had with the people in their lives or the jobs they’ve settled for. What they do along the way in their search doesn’t matter to them, because they aren’t happy . . . which means they can break the law, dispose of people in their lives like trash, and succumb to whatever they feel like doing at any moment.


Author Jack Kerouac

There is an appeal to their lives—they can abandon anything that ties them down, and hit the open road with more energy than anyone else. There is something impressive about their ability to relinquish everything. This is Kerouac’s connection to the Beat generation of literature—a group of artists after WWII who celebrated the beaten-down-ness and the beauty of their lives. This group found interesting ways to challenge social norms while creating new methods of art, and On the Road is one of the most powerful novels that sum up the Beat generation of artists.

But the idea of abandonment is taken too far, at least for me, by the way the characters treat others. Sal and Dean just as easily abandon the rules of kindness, and their recklessness never fails to hurt others. Their sexism and homophobia also get under my skin, even if it fits with both their lifestyle of abandonment and American society of the time. They are powerful characters, but they are incredibly unlikable.

Still, On the Road always comes back to what makes it special: a poetic voice that captures America. The road trips show off the variety of American landscapes and people—the frontier of the West, the wilderness of the East, the oppressive humidity of the behind-the-times South, the jungle of Los Angeles and the cloudy closeness of New York . . . it’s all remarkable through Sal’s eyes. I can’t to justice to Kerouac’s language, so that you’ll have to read yourself.


Up next is a novel I’ve been reading for a while, alongside the last several books I’ve posted about. I’ll probably need more than a blog post to write about James Joyce’s Ulysses, but I’ll try to keep it short! But it’s one of my favorite novels of all time, and I can hardly wait to tell you why you should read it.

Until next week,

Prof. Jeffrey

“What is that feeling when you’re driving away from people and they recede on the plain till you see their specks dispersing?—it’s the too-huge world vaulting us, and it’s good-by. But we lead forward to the next crazy venture beneath the skies.”

—from On the Road by Jack Kerouac

“I thought all the wilderness of America was in the West . . . No, there is a wilderness in the East; it’s the same wilderness Ben Franklin plodded in the oxcart days when he was postmaster, the same as it was when George Washington was a wild-buck Indian-fighter, when Daniel Boone told stories by Pennsylvania lamps and promised to find the Gap, when Bradford built his road and men whooped her up in log cabins.”

—from On the Road by Jack Kerouac

Off-Topic: Poetry Favorites (Part 2)

Hello again, class.

There’s a lot of poetry out there, so I’m following up on my last post about my favorite poems! Be sure to check out my previous post to see the poems I’ve already written about.

I’ve included links to Poets.org for the full poems below. (Once again, as sort of a disclaimer, I’ve only chosen English poetry…I have zero expertise in poetry from other languages, and I wish I did. These are some of the best English-language poems I know.)


This poem is not one I would usually call a favorite, but it’s grown on me for its subtlety. Wheatley was one of the first black poets in America, and her work challenged beliefs about racial treatment and humanity. In this poem, Wheatley praises God’s mercy for being revealed to her, and celebrates God leading her to a new land. She carefully warns others that anyone can be a Christian, and anyone can be redeemed—even men and women from Africa. That’s a message that was sorely needed at the time, and has challenged prejudice and injustice to this day.

If you’ve ever seen Dead Poets Society, you know this one. Whitman asks the “To be or not to be” question: what’s the point of life? What good comes from living? The answer is that the powerful play of life goes on, and we can contribute a verse to that play. The poem is a simple and powerful understanding of life, worth reading every time.

A professor once told me that the best way to read and understand this poem is to get very drunk (his exact word was PLASTERED) and then read it. While I haven’t followed his advice, I can see where he’s coming from—this is a very long and complicated poem, and all of the helpful meaning has been filtered out. But it also captures the chaos and decay of the time; Eliot’s thoughts on the collapse of society, the terror of war, the brave new world around the corner . . . the poem does a really great job of capturing those themes. I discover something new every time I read it.

I know of no other poem about suicide, and I certainly don’t know any piece of art that glorifies it in this way. It’s off-putting, but it continues to draw me in. Sylvia Plath, who committed suicide in 1963, was writing about such dark themes very personally, and this poem reflects it by including Nazi imagery and graphic moments of bodily decay. It’s hard to read about her suicide attempts, but it is powerful, emotional poetry that shakes me.

The link above is to a picture of this poem on a wall in Charlotte, NC—I couldn’t find the poem anywhere else. It’s a simple poem about two people in love, but it’s also about the choice to love someone . . . a choice we face again and again. It’s a choice people face when they meet for the first time, and it’s a choice years later. But there is also the question that something external chose these lovers: God, the universe, or maybe the luck of the draw. It’s empowering and humbling poetry. The man who wrote it was a professor of mine in college, who continuously inspired me to write, and for that it’s personally special as well.

This piece of prose poetry is from Rankine’s incredible Citizen: An American Lyric (2014), portraying racism in modern America. Rankine describes a train (or any and all public spaces) where a black man sits next to an empty chair while another woman stands, uncomfortable sitting next to him. The speaker sits next to him, and in that simple action they form a bond that is close to family—a defiance of racial attitudes, of fear, and of injustice. Most of Citizen does this as well, but this is one of the more powerful passages.


Make sure to take a look at each of these! In the comments, tell me your favorite poems—I’m always down for reading more poetry.

Until next week,

Prof. Jeffrey

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