When I was in college, I made the mistake of telling a teacher that I was never going to read James Joyce’s Ulysses. My teacher promptly assigned it as my required reading for the term. Stubborn as I can be about such things—on the other end of the cultural spectrum, I refuse, to this day, to watch Titanic—I’ve always been an obsessively good student, so I caved immediately. It took me about nine months to get through it, and I finished, entirely by coincidence, on “Bloomsday”—June 16, the date the book takes place.
I discovered, one difficult page at a time, that Joyce’s novel isn’t merely important, but also funny, raunchy, and delightfully weird. A decade later, I still remember the keen pleasure of burrowing into a story that requires that kind of close attention; it feels like intimacy.
Literature should not be something we approach out of a sense of duty. But many lengthy, complex, and well-known books really are that good. Like taking a long hike or following a tricky recipe, engaging with writing that challenges you can be deeply satisfying. Each of the books below is demanding in its own way, and reading or rereading them can be a fascinating, beautiful, and rewarding experience.
The Tale of Genji, by Murasaki Shikibu (translated by Dennis Washburn)
Written by a noblewoman known only as Murasaki Shikibu, this 11th-century work of Japanese fiction predates the very term novel. But contemporary readers will feel at ease with The Tale of Genji, especially in Washburn’s highly accessible translation. The tale opens with imperial drama: The emperor’s favorite concubine gives birth to a son, and to appease his higher-ranking wives, he removes the infant Genji from the line of succession. Genji is raised as a commoner, but it’s no secret that he’s the emperor’s child, and he’s beloved for his looks, intellect, and talents. But the “radiant prince,” as he’s called, is far from perfect: “In fact,” the sly narrator tells us, “his failings were so numerous that such a lofty sobriquet was perhaps misleading.” Genji is an unrepentant womanizer who’s also remarkably sincere; his life revolves around climbing the court’s political ladder and making waves at its ceremonial events. As he continues into middle age and beyond, he grows more contemplative, meditating often on how fleeting life is. Full of intrigue, foibles, pranks, and secret affairs, The Tale of Genji is both lusher and more clever than any HBO show.
Moby-Dick, by Herman Melville
Like many young adults, Ishmael, the narrator of Melville’s grand adventure of the body and mind, is feeling restless and has little money in his purse. The only solution, as far as he’s concerned, is to go to sea and experience a life away from shore. The ship he chooses sets sail on Christmas, but he’s eager: “Spite of this frigid winter night in the boisterous Atlantic, spite of my wet feet and wetter jacket, there was yet, it then seemed to me, many a pleasant haven in store.” Although Moby-Dick is eventful (seafaring is no picnic), it’s also an exploration of the mind of one man as he throws himself into the unknown. Ishmael’s captain, Ahab, is driven by a single desire: catching the whale that bit off part of his leg. Ishmael, in contrast, is curious and open-minded, eager to learn and experience all that he can. In recent years, Moby-Dick’s fandom has expanded, perhaps because the book provides both an escape from the world and a deep immersion in it, whales and all.
Vanity Fair, by William Makepeace Thackeray
Becky Sharp has the misfortune of being born to a poor art teacher and an opera artist, and Vanity Fair follows her young adulthood as she and her peers begin the work of becoming proper 19th-century Englishwomen. Some try to be good, but Becky longs to be in charge: She learns that in order to gain money and status, she must be “agreeable to her benefactors, and … gain their confidence to the utmost of her power.” Witty, charming, and a fantastic mimic, Becky makes herself extremely agreeable—especially to men, who keep falling in love with her—and worms her way into wealthier and more influential circles. Her need for financial stability is entirely understandable, and although her methods for getting it are questionable, it’s hard not to root for her. Becky’s lies eventually stack up, and her dramatic rise to prominence is equaled only by her fall from grace. Funny and biting, Vanity Fair is social critique at its best.
Middlemarch, by George Eliot
In 1871, when Eliot was writing Middlemarch, Britain had recently undergone some 40 years of social upheaval. The First and Second Reform Acts enfranchised men of lower means and pedigree, broadening the voting public to include more than just the wealthy and noble few. But her mammoth novel takes place in the lead-up to that change, and it explores the tensions between rich and poor, rural and urban, old and new. The story follows Dorothea Brooke, a wealthy and pious 19-year-old orphan living with her sister and her uncle, and Tertius Lydgate, a sweetly naive and eager doctor, as each falls in love, marries, and discovers that a lot follows the expected happily-ever-after. Subplots abound, of course, as this is a lengthy and intricate “Study of Provincial Life” (the novel’s subtitle), but the love triangles, political maneuvering, and intricate gossip in the titular English town make for a thrilling read. This is a book about wonderfully and frustratingly messy people.
Almanac of the Dead, by Leslie Marmon Silko
Some readers might be more familiar with Silko’s beautiful Ceremony, which follows a Pueblo World War II veteran after his return to the reservation he grew up on. Her later book Almanac of the Dead is a whole other (and much larger) beast—although it is equally, and perhaps more, brilliant. It starts in Arizona, where a white woman named Seese begins working for Lecha, a psychic. Lecha and her twin sister, Zeta, each have a unique gift: Lecha can find the dead, and Zeta can communicate with snakes. Lecha is also tasked by her grandmother to complete and preserve the Almanac of the Dead: ancient documents—complete with additions, re-creations, and notes made over the years—that recount history and predict the future. Her quest, however, is just one thread in Silko’s epic, and the author virtuosically spreads the action across continents and years without losing sight of details. Eventually, and impressively, the stories of the novel’s sprawling cast flow into one another, plot spilling into an ocean of beauty and menace. The brutality of colonialism and capitalism are laid bare, tempered only by the belief in a better world to come.
Infinite Jest, by David Foster Wallace
Wallace’s fans may have a reputation for being insufferable, but Infinite Jest itself, although no easy read, is a ridiculous and satisfying journey. Exploring addiction, masculinity, zealotry, and the absurdity of war, the novel is strewn with bread crumbs, many of which are in the prodigious endnotes. It can be a pain to keep flipping between the main text and the back, but some of the most uproarious moments take place in the small font. The setting is superbly bizarre: a version of our world where Canada, the U.S., and Mexico have become one supernation; years are no longer known by numbers but are instead sponsored by corporations (“Year of the Whopper”); and a cultish Quebecois terror cell seeks a copy of a movie that makes every person who watches it want to do nothing but keep watching it, over and over, until they die. Against this backdrop, Hal Incandenza, a tennis prodigy and teenage genius, attends the athletic academy run by his family, spends time with his variously strange friends, and tries to sort through his many issues. Some associate Wallace’s work with a kind of unchecked toxic masculinity, but Infinite Jest evokes it deliberately: Its pathetic and pompous men function as a searing critique of the very cultural messages handed down to them.
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