7 Most Heartbreaking Books of All Time, Ranked

Since the days of Ancient Greece, many works of literature have aspired to take their readers on painful emotional journeys, a symbolic purgation of emotion that Aristotle called catharsis. Despite the thousands of years that have passed since then, the idea has stayed firmly planted in our cultural consciousness, and there’s no denying the fact that we all enjoy a powerful, heartbreaking read every once in a while. Over the years, there have been plenty of books that fit the bill, including both those drawn on personal experiences and stories of fiction that nonetheless evoke the same emotion.

From stories set against the backdrop of horrific events to more personal tragedies rooted in everyday pain, these heartbreaking books seek out the uncomfortable and even traumatic and transform them into something uplifting, inspiring, and beautiful. In the process, they’ve also earned widespread acclaim and sold millions of copies around the world, earning their places in both our libraries and the bestseller lists. So, if you’re in the mood for a read that will truly shatter your heart in the best ways possible, we’ve got you covered. Read on to discover our ranked selection of the most heartbreaking books of all time, including both modern hits and timeless classics.

7

‘The Fault in Our Stars’ (2014)

John Green’s fourth solo novel, The Fault in Our Stars is a tragic young adult romance novel that centers on 16-year-old Hazel Grace Lancaster, who suffers from thyroid cancer that has spread to her lungs. Forced to attend a support group by her parents, Hazel meets and falls in love with 17-year-old cancer survivor Augustus Waters. Bonding over their shared love of books, the two plan a trip to Amsterdam to meet the author of their favorite novel.

A best-selling book that broke the hearts of a whole generation of fans, The Fault in Our Stars is both bitterly tragic and a life-affirming coming-of-age story. Sweet, funny, and often melancholic, the novel lives and breathes with its characters, who are easily among Green’s most endearing. Arguably the author’s best book, The Fault in Our Stars was adapted as a 2014 feature film directed by Josh Boone and starring Shailene Woodley and Ansel Elgort, which was similarly successful.

6

‘The Song of Achilles’ (2011)

Image via Ecco Press

Written by Madeline Miller, The Song of Achilles is a reimagining of Homer’s Iliad, approaching the story of the Trojan War from the perspective of Patroclus. The book recounts Patroclus’s early life, his initial encounter with Achilles, the development of their relationship, and their exploits during the war. Though largely inspired by the Iliad, the novel also draws from other sources and makes a few changes to the original mythology.

Published in 2011, The Song of Achilles was well-received by critics and awarded the Orange Prize for Fiction, but it’s only in the 2020s that the book became a major bestseller. With over 2 million copies sold across formats, the novel is a highly popular and influential take on the romance of Achilles and Patroclus, capturing deep emotion in their fate-crossed story. It’s painful and tragic, but also deeply poetic, and a brilliant read overall.

5

‘The Book Thief’ (2005)

Image via Alfred A. Knopf

Written by Australian author Markus Zusak, The Book Thief is a historical fiction novel that follows the adventures of a young girl in Nazi Germany. The story is narrated by Death, who reveals the story of Liesel Meminger, who lives with foster parents Hans and Rosa Hubermann and, recognizing the power of literature, begins to steal books to read. As bombs fall around her and she loses all the people she knew and loved, Liesel’s love of reading and writing carries her to the very end of her life, when she finally speaks with Death.

First published in 2005, The Book Thief is an acclaimed international bestseller that has sold over 17 million copies around the world and inspired countless readers with its powerful story. It unravels a deeply moving narrative with themes of death, love, and the value of sharing stories — one that’s sure to resonate with any lover of literature and break the hearts of plenty more as well. A feature film based on the novel was released in 2013, and the book has also inspired a musical.

4

‘Hamnet’ (2020)

Image via Tinder Press

Written by Maggie O’Farrell, Hamnet is a work of historical fiction that presents a fictional account of the death of its titular character, the son of William Shakespeare and Agnes Hathaway. Focusing primarily on Agnes, the novel chronicles the couple’s meeting, courtship, marriage, and other events leading up to the death of their only son. From there, it explores the fracturing of their relationship amid overwhelming grief, culminating years later when Shakespeare stages a new play called Hamlet.

Combining known facts of the legendary playwright’s life with fiction, Hamnet is a book about the untold history of grief. Charged with emotion and intensely cathartic, the novel explores a key moment in the Bard’s life that is known of but not known about, filling in the gaps with imagination and a touch of literary magic. The novel received several accolades when it was published in 2020 and was adapted as an Oscar-winning film directed by Chloé Zhao, starring Jessie Buckley and Paul Mescal.

3

‘Kafka on the Shore’ (2002)

Image via Knopf

Written by Japanese author Haruki Murakami, Kafka on the Shore is a magical realist novel that follows the stories of young runaway Kafka Tamura and elderly, mentally disabled man Satoru Nakata. Cursed by his father, Kafka leaves Tokyo for Shikoku, experiencing a series of surreal events along the way. Meanwhile, Nakata, who possesses the ability to talk to cats, finds himself called on a quest that takes him far away from his home, guided by the universe and an ineffable force.

First published in 2002 and translated into English in 2005, Kafka on the Shore is a highly acclaimed and award-winning novel that has inspired generations of readers. The book isn’t heartbreaking the same way many of the other entries on this list are. However, there is a pervasive sense of melancholy that suffuses the narrative, balanced by its meditations on metaphysics, philosophy, and fate, as well as its surprising sense of humor. The novel is many things to many people; it’s transformative, cathartic, spiritual, sexual, satirical, and yes, heartbreaking, all at the same time.

2

‘And the Mountains Echoed’ (2013)

Image via Riverhead Books

The third novel written by Afghan-American author Khaled Hosseini, And the Mountains Echoed chronicles the lives of multiple characters living in and around Kabul, Afghanistan. The book primarily follows the story of 10-year-old Abdullah and his younger sister Pari, whose lives take them oceans apart, touching the lives of many others along the way. The novel is a departure from Hosseini’s previous books, which follow a more traditional narrative, but features similar themes of family and loss.

Using sibling relationships as a consistent theme, And the Mountains Echoed takes readers through a series of human and realistic stories, each with its own complexity, and paints an overall picture of Afghanistan, identity, and transformation. It’s a powerful, engrossing novel that’s been critically acclaimed and has sold millions of copies around the world. Though relatively underrated compared to Hosseini’s previous work, And the Mountains Echoed is an experience that’s both deeply painful and yet overflowing with love.

1

‘The Diary of a Young Girl’ (1947)

Image via Contact Publishing

Commonly called The Diary of Anne Frank, The Diary of a Young Girl is a book that’s practically synonymous with its young author. A German-born Jewish girl who lived in the Netherlands during the Nazi occupation, Anne Frank was captured and sent to a concentration camp, where she died at the age of 15. The book collects writings from her diary, written during her two years in hiding and given to her father, Otto Frank, the sole survivor of the family, at the end of World War II.

To say that The Diary of a Young Girl is one of the most heartbreaking books ever written would be an understatement. The book captures the daily thoughts and life of its young author as she lives through one of humanity’s darkest chapters, chronicling her search for friendship, her inner development, and her enduring hope in the face of unspeakable horror. The book has been critically and popularly acclaimed ever since it was first published in 1947, and it continues to break the hearts of millions around the world today.

The Diary of Anne Frank

Release Date

August 19, 1995

Runtime

102 Minutes

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  Reina Takahashi

  Anne Frank

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  Jiro Sakagami

  Hermann van Daan

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