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Sometimes, what you need from a book is a good, hard cry. Here are a few tear-jerky titles that will take you on an emotional roller-coaster ride. 

I tried to stay away from sentimental books and go instead for books that grapple with universal human dilemmas and the fallout of our choices.

This book list accompanies Vol. 6 of The Novel Envelope, which features Anton Chekhov’s short story “Misery.” It’s a sad one. Not every book on this list requires antidepressants—phew!—but they will all tug on your heartstrings.

Handing you a hanky…

Les Misérables by Victor Hugo

Epic in scope but intimate in emotion, this bucket-list book reveals the moral grandeur and suffering of ordinary souls caught between justice and mercy. I give you full permission to skip the essays (yes, Hugo intersperses his novel with essays on French culture and politics). If you read only the plot-driven chapters, you’ll be fine. 

Ethan Frome by Edith Wharton

Bleak, wintry, and tragic. A haunting look at unfulfilled desire, duty, and the crushing power of circumstance. 

Of Mice and Men by John Steinbeck

A short, piercing novel of friendship, dreams, and mercy. Its ending is quietly shattering in its moral weight.

The Diary of a Young Girl by Anne Frank

Not fiction, but a timeless testament to hope, innocence, and the fragility of life. It’s a book that breaks hearts precisely because it insists on seeing beauty in the midst of horror.

A Christmas Carol by Charles Dickens

Watching Scrooge feel sorrow for his wasted years and embracing the chance to change before it’s too late never fails to bring happy tears to my eyes at Christmastime.

A Tree Grows in Brooklyn by Betty Smith

A coming-of-age story filled with poverty, hope, and resilience. It will have you shedding tears of both sorrow and joy.

To Kill a Mockingbird by Harper Lee

Innocence lost, moral courage tested. This timeless story breaks your heart because of its tenderness and truth. The scene where Scout recognizes the men at the prison gets me every time.

The Book Thief by Markus Zusak

A young girl, a foster family, and the power of words amid the horrors of war. This book is both tragic and luminously written. It’s fabulous on audio. 

Mrs. Mike by Benedict and Nancy Freedman

Set in the Canadian north, a young couple faces nearly every crisis that life could possibly throw at them. It goes to some incredibly sad places, but it brings you back into the light, wiser and stronger.

The Light Between Oceans by M. L. Stedman

A childless couple living alone on a lighthouse island off the coast of Australia. One day, a boat carrying an infant washes ashore. What do they do? This book forces you to grapple with impossible dilemmas.

Hamnet by Maggie O’Farrell

We don’t know much about Shakespeare, but we do know that shortly after his son, Hamnet, died of the plague at age 12, his father staged his most famous play, Hamlet. What might have been the backstory? That’s what O’Farrell explores in this edgy imagining. 

A Lantern in Her Hand by Bess Streeter Aldrich

How do you measure a mother’s impact? This beautiful—but, admittedly, meandering—novel shows what a strong woman accomplishes when homemaking is her life’s work. 

The Blue Castle by L. M. Montgomery

I didn’t cry when Elizabeth and Darcy got together. But I did cry at the climax of this sweet love story. This is one of Montgomery’s few adult standalone novels, and it’s worth every minute of reading to get to the end.

The Best Christmas Pageant Ever by Barbara Robinson

While this Christmas classic is mostly laughs, it also cuts straight to the heart of why we go to church. There’s nothing like a crew of miscreant kids in Sunday school to show you what your heart is really made of.

Our Only May Amelia by Jennifer Holm

I wasn’t expecting this book to be such an emotional roller coaster. It had me laughing one chapter, and the next devastated by the harshness of life on the river. 

Sweep by Jonathan Auxier

A quirky middle-grade novel starring a scrappy chimneysweep and her, um, monster—a golem to be exact. It sounds weird, but if you have any heartstrings at all, this tale will most certainly tug on them.

Where the Red Fern Grows by Wilson Rawls

My fifth-grade teacher read this book aloud to the class. At the end, there wasn’t a dry eye in the house. I’m talking 10-year-old boys either weeping or raging, depending on their personalities. That symbolic red fern stays with me still.

Bridge to Terabithia by Katherine Paterson

Paterson wrote this book for her son when he was coping with the death of a classmate. When my nephew was young, we watched the movie together, and he told me later, “I went home that night and cried!” You’ve been warned.