25 Challenging Books You Should Read This Summer

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Your vacation downtime is the best opportunity you'll have to tackle a big, difficult read this year, so I've picked out 25 challenging books you should read this summer. The novels, story collections, and memoirs on the list below are thick, lyrical, complex, and stunning — which means they're worth the time you spend with them, even if you don't read through them quite as fast as the other books on your TBR.

It should go without saying that every book ever written has challenged at least one reader in some way. If you didn't find many of the books on this list to be difficult reads, that's OK! I've picked out 25 books that will challenge readers on all kinds of levels, from thematic to structural. No matter what type of books you're used to reading, however, you can rest assured that any of the titles below will bear little resemblance to the novels you normally pick up.

Check out the 25 challenging books I've picked out for your summer reading list below, and select one or two to take on vacation with you. You won't regret it, I promise.

'The Travelers' by Regina Porter

Amazon

Regina Porter's debut novel is a family epic that follows two families, one white and one black, from the 1950s through the first year of Barack Obama's presidency. It's a sprawling, twisting novel, told in intimate, out-of-chronological-order vignettes, with a broad cast of characters that you can lose track of if you aren't careful. Set over a half-century of tumult, The Travelers is not for the faint of heart, but it's a rewarding read to finish.

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'A Little Life' by Hanya Yanagihara

Amazon

Hanya Yanagihara's award-winning A Little Life follows four college friends who move to New York to begin their lives. Where adulthood and its complications would pull others apart, three of the men are drawn to one another through their connections with the fourth, Jude, who has been the victim of an unresolved trauma. Jude's experiences are not easy reading, but the gut-punch of a story Yanagihara delivers here will stick with you long after you've turned the final page.

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'The Old Drift' by Namwali Serpell

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Another debut, Namwali Serpell's The Old Drift opens in 1904 Rhodesia, in what is now known as Zambia, as three families' lives become inextricably tangled by a swift domino effect of events. An angry white colonizer rips hair from the head of an Italian hotelier, whose daughter lashes out by striking an innocent, black pedestrian, giving him a brain injury. So complex a story that it includes family trees to help the reader keep track of who is who, The Old Drift is a magnificent feat of magical realism that must not be missed.

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'The Goldfinch' by Donna Tartt

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Clocking in at nearly 800 pages, Donna Tartt's Pulitzer Prize-winning novel is a tome of a novel that has plenty to offer the reader with the endurance to finish it. The story centers on Theo, a precocious 13-year-old, who is adopted into a wealthy family with art-world connections after his mother dies in a museum explosion. As Theo grows, he explores his relationship to his missing parent through the life and work of a Dutch painter who died in an eerily similar fashion.

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'Milkman' by Anna Burns

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Set in the midst of the Irish Troubles, Anna Burns' Booker Prize-winning novel, Milkman, centers on an 18-year-old, known only as the "middle sister" of her family's 10 children. She is rumored to be the girlfriend of a now-dead political dissenter, the eponymous milkman, who was, in fact, her stalker. Written with somewhat of an expectation that you'll know what happened during the Troubles, and dreamlike in its flashes backward and forward in time, Milkman may be difficult to grasp, but you'll want to read it all the same, if only to get in on the hype.

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'Nightwood' by Djuna Barnes

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Djuna Barnes' Nightwood is well-known as a classic of lesbian literature, a key roman à clef in the Modernist tradition, and an incredibly difficult novel to read. Writing in the novel's preface, T.S. Eliot says Nightwood "is so good a novel that only sensibilities trained on poetry can wholly appreciate it." Clocking in under 200 pages, Barnes' novel is short enough for you to challenge yourself to read it in a weekend.

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'The Water Cure' by Sophie Mackintosh

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When a man who has trapped his wife and daughters on an otherwise-uninhabited island disappears, the women must figure out how to protect themselves from the dangers of the outside world in Sophie Mackintosh's Booker Prize-nominated novel. The Water Cure is a heady novel, with a story full of difficult-to-read moments and subtext, but worth reading for its timely, otherworldly story.

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'Wolf Hall' by Hilary Mantel

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The book that won the Man Booker Prize for its "sheer bigness," Hilary Mantel's Wolf Hall is a daunting tome, the reading of which is not for the faint of heart. Coming in at just under 700 pages, this work of stunning historical fiction tracks the rise of Thomas Cromwell in the court of Henry VIII.

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'Confessions of the Fox' by Jordy Rosenberg

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In this "mind-bending" novel, a trans academic uncovers the purported confessions of Jack Sheppard and Edgeworth Bess — two real-life, 18th-century criminals who pulled off amazing acts of thievery and daring escapes. According to the manuscript, Jack was a trans man, and Bess an Asian-British woman, but the academic at the heart of Jordy Rosenberg's debut must work out whether or not the story is authentic.

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'Kristin Lavransdatter' by Sigrid Undset

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A saga that won Sigrid Undset the Nobel Prize in Literature, Kristin Lavransdatter centers on its eponymous heroine as she navigates life in 14th-century Norway, breaking her betrothal to the man her family has chosen for her in order to marry the one she loves. With more than 1,000 pages in the collected trilogy, Undset's novel is a vast undertaking to read, but rewards its fans with an engaging story of medieval life.

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'The Third Hotel' by Laura van den Berg

Amazon

This psychological novel centers on widowed heroine Clare, who spots her husband, Richard, on the streets during a vacation in Havana. There's just one problem — Richard is supposed to be dead. The story of The Third Hotel unwinds as Clare follows Richard through the Cuban streets, becoming increasingly unsure of what she remembers. As gripping as it is challenging to follow, Laura van den Berg's novel belongs on your nightstand.

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'The Inheritance of Loss' by Kiran Desai

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In this Booker Prize-winning novel, a retiring judge finds his world turned upside down when his orphaned, teenage granddaughter comes to stay with him. As the narrative drifts from the judge, to his cook, to the cook's son and the judge's granddaughter, and to her tutor-slash-lover, Kiran Desai weaves a bittersweet, nuanced story of heartbreak that will stick with you long after you've finished The Inheritance of Loss.

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'Hardly Children' by Laura Adamczyk

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A short-story collection, Laura Adamczyk's Hardly Children pieces together dark stories just weird enough to be believable. From the kidnapping of children to messages written in human hair, Adamczyk's little glimpses into the eerie underside of our world may disturb you enough to put you off finishing the book — but you need only to read another page to be hooked again.

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'The Idiot' by Elif Batuman

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A slow-building novel about a Turkish-American student's first year at Harvard, Elif Batuman's The Idiot pitches readers into the mind of Selin, who tells her story in vignettes and snippets that work together to form a whole. Readers may have to work hard to get to know Selin and her circle, but the payoff is making a wickedly smart new friend in Batuman's heroine.

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'The Heavens' by Sandra Newman

Amazon

A novel based in part on dream logic, Sandra Newman's The Heavens follows Kate, a young woman living in pre-9/11 New York City, who lives a separate life at night, when a recurring dream transforms her into Emilia, a court lady in Elizabethan England. As Kate/Emilia begins to lose touch with which of her lives is the real one, the novel catches readers in its protagonist's mental vortex. If you love psychological novels, you'll enjoy the challenge posed by The Heavens.

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'Almanac of the Dead' by Leslie Marmon Silko

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In Tucson, the lives of two retired sisters, the drug-addicted mother of a lost child, and a Laguna man living in exile twist and twine together to tell an enticing story of international intrigue and local conflict. A complex novel that may spiral out of some readers' control, Leslie Marmon Silko's Almanac of the Dead is a poetic tale that's worth the investment of time and energy to read.

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'Winter Loon' by Susan Bernhard

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Susan Bernhard's novel opens on a teenage boy, stranded in the center of a frozen lake, with no one around for miles. As Winter Loon recalls the details of young Wes' life, it also uncovers his family's trials, tragedies, and horrendous secrets — the narration of which makes the novel difficult, and sometimes painful, to read.

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'Beloved' by Toni Morrison

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Another novel rendered challenging by its thematic elements and dreamy structure, Toni Morrison's Beloved centers on Sethe, a freedwoman living in a Cincinnati home haunted by the vengeful spirit of her dead child. A poignant and sometimes painful tale, Beloved is a Pulitzer Prize-winning classic that belongs on your reading list.

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'Idaho' by Emily Ruskovich

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In her award-winning debut, Emily Ruskovich follows Ann, a woman living with her elderly husband, as she attempts to solve the mystery of what happened to the man's first wife, a woman named Jenny, and their daughters. Somewhere in their shared past, a horrible event put Jenny in jail, and that same tragedy continues to affect the lives of Ann and her husband in the novel's present.

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'The Piano Teacher' by Elfriede Jelinek

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From Nobel laureate Elfriede Jelinek comes this dark and often disturbing novel about a middle-aged music instructor's exploration of her aberrant sexuality. Thirty-eight-year-old Erika, who lives at home in spite of her teaching position at a local conservatory, frequents peep shows and harbors a longing for human connection — one that may spiral out of control when a teenage student begins to flirt with her.

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'The Western Wind' by Samantha Harvey

Amazon

A 15th-century village priest must unravel the tangle of events surrounding a man's unnatural death in this complex novel from Dear Thief author Samantha Harvey. After the body of the wealthiest man in town washes ashore, John Reve, who has heard the village's confessions, is tasked with determining whether the death was murder, accident, or suicide. The story is challenging, but Reve's narration guides readers through to its conclusion.

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'Human Acts' by Han Kang

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Set in the aftermath of the Gwangju Uprising in 1980 South Korea, Han Kang's Human Acts focuses on the death of one boy, Dong-ho, who is younger than the rest of the student protesters. Telling the stories of Dong-ho and others killed in by police and military force, Human Acts winds its way through the events of that fateful day, leaving readers to parse out the details before reaching an uplifting conclusion.

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'On Earth We're Briefly Gorgeous' by Ocean Vuong

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Celebrated poet Ocean Vuong's first novel takes the form of a letter from the narrator to his illiterate, immigrant mother. Protagonist Little Dog recounts his family's history, beginning in Vietnam before his birth, confessing to his mother the things about him she does not know. A poignant and poetic novel, with painful moments that may prove difficult for some readers, On Earth We're Briefly Gorgeous is a stunning debut that you owe it to yourself to read.

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'Ice' by Anna Kavan

Amazon

An experimental work of science fiction, Anna Kavan's Ice follows two men as they search for a young woman who has gone missing out in the frozen, post-apocalyptic landscape. One of them is the woman's husband, who keeps her captive. The other is the narrator, a man conflicted by his feelings for their target. Hazy and ethereal, Ice is a challenging novel that's sure to be unlike anything else you have read.

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'Shout' by Laurie Halse Anderson

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From Speak author Laurie Halse Anderson comes this memoir, told in free-verse poetry, about the real-life events that informed her bestselling YA novel. Anderson's fans may find it difficult to take in her true story, but Shout's rallying cry to end violence against women and girls is inspiration that shines through the tearful reading.

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