8 Timeless Books That Will Make You Cry: from Classics to Contemporary Masterpieces

Explore eight stories with emotional resonance, cultural and historical significance, and timeless lessons for every generation. 

By Julie Tyler Ruiz

CONTENTS:

• Why should we read tear jerkers?
• How I compiled this book list
• 8 timeless books that will make you cry

Why should we read tear jerkers? 

Reading tear jerkers offers a unique kind of catharsis, a deep emotional release that we often need but may not get during the course of everyday life. Tear jerkers take us on carefully crafted emotional journeys, as we follow characters through their struggles and triumphs. They help us process our own emotions and contemplate more deeply what it means to be human. 

Beyond the emotional release and life lessons, tear jerkers help us connect with others. In seeing the world through the eyes of fictional characters, we learn to feel empathy and compassion, not only for people who exist only on paper, but also for each other. 

How I compiled this book list

To compile this list of tear jerker books, I set out to represent a wide range of fictional topics, genres, styles, and time periods—from the classics to contemporary masterpieces. I reviewed popular book lists, unearthed hidden gems, and scoured my own bookshelf for books that have made a deep emotional impact on me.  

I chose each of the eight titles for its literary value, cultural and historical significance, and commercial success, as well as its ability to transcend cultural and generational differences. 

But beyond the literary and commercial considerations, this list is intensely personal. Each book here is one I would wholeheartedly recommend to fellow readers who seek catharsis and new insights about life. Ultimately, the most important reason factor in my selection was whether the book actually brought me to tears. 

These eight stories did, and I believe they'll offer the same experience for you.  

8 timeless books that will make you cry

Below, you'll find my carefully curated list of tear jerkers, arranged by publication date. For each book, I've included links to the author's page and purchase options, along with a brief plot summary and my personal take on why it's worth reading and sure to draw tears. To give you a taste of the emotional depth and thematic resonance within each book, I've also included a quote that has stuck with me over the years. 

Explore eight stories that will leave a lasting impact: 

Anne of Green Gables, p. 1908

Author: Lucy Maude Montgomery

Links to purchase: Amazon Kindle Edition, Simon & Schuster

Plot summary: Anne Shirley, an imaginative and spirited orphan, is mistakenly sent to live with Marilla and Matthew Cuthbert, an elderly brother and sister who intended to adopt a boy to help on their farm in Avonlea, a fictional town in Prince Edward Island, Canada. Despite the initial misunderstanding, Anne's vibrant and loving personality win over the Cuthberts and the rest of the community. As she grows up, Anne faces various challenges and adventures, experiencing friendship, family and a true sense of belonging. 

My take: Anne of Green Gables is worth reading for the way it captures the profound bond that develops between Anne and her adoptive parents. Watching their love for Anne blossom as she brings levity and laughter into their lives is deeply moving. Anne's sincerity and infectious spirit make her impossible not to root for, especially as we see her thrive in the care of Matthew and Marilla. The story is filled with moments that make us laugh at Anne's quirky antics. It also brings us to tears as we share in her disappointments and losses, most poignantly when [spoiler alert] Matthew passes away. This blend of joy and sorrow makes Anne of Green Gables a truly emotional read.  

"Kindred spirits are not so scarce as I used to think. It's splendid to find out there are so many of them in the world." —Anne Shirley

The Phantom of the Opera (Le Fantôme de l'Opéra), p. 1910

Author: Gaston Leroux

Links to purchase: Amazon Kindle Edition, Canterbury Classics

Plot summary: The Phantom of the Opera is a gothic novel set in Paris in the 1880s, with much of the action occurring in the Paris Opera House. The story follows Christine Daaé, a young soprano, who becomes the object of obsession for a mysterious figure known as the Phantom. The Phantom, whose real name is Erik, lives below the Opera House in the labyrinth of cellars and passageways.

As a musical genius and a disfigured outcast, he gives Christine voice lessons while hidden in the labyrinth behind her dressing room door and calls himself "the Angel of Music" to gain her trust. When Christine falls in love with her childhood friend Raoul, the Phantom becomes dangerously jealous and resorts to murder and abduction. The story reaches a dramatic climax when the Phantom gives Christine an ultimatum, agree to live with him forever in the labyrinth or refuse and send Raoul to his grave. 

My take: The Phantom of the Opera is a powerful read that takes us into the complexity of the title character, his cruelty, genius, and humanity, and offers a backstage look at the world of opera. Through the author's dynamic portrayal of the Phantom, we can't help but experience both loathing and compassion for this figure who performs dreadful acts and yet lives a life of isolation and rejection. The most heart-wrenching part of this tale is the Phantom's final act of selflessness as he [spoiler alert] releases Christine and subsequently disappears. 

"If I am the Phantom, it is because man's hatred has made me so. If I am to be saved, it is because your love redeems me." —the Phantom

Catcher in the Rye, p. 1951

Author: J.D. Salinger

Links to purchase: Amazon Kindle Edition, Hatchett Book Group

Plot summary: The Catcher in the Rye follows Holden Caulfield, a cynical teen who, after being expelled from his prep school, wanders through New York City for several days, seeking out connection, while bemoaning the phoniness of the adult world. As Holden struggles with issues of identity and alienation, he reflects on his desire to protect innocence, particularly that of his kid sister Phoebe. 

My take: The Catcher in the Rye is essential reading for anyone who yearns for more authenticity. Through Holden's journey we confront our own phoniness and loss of innocence. I've always loved the narrative voice of this novel. Although Holden's vocabulary is limited to the vernacular of a 1950s teen, Holden offers a sharp and insightful interpretation of the world around him. For me, the tear jerker moment comes at the end when Holden takes Phoebe to a playground. Her demeanor toward Holden is so childlike, innocent, and sincere, while Holden's cynicism melts in the warmth of his love and admiration for her. 

"Anyway, I keep picturing all these little kids playing some game in this big field of rye and all. Thousands of little kids, and nobody's around—nobody big, I mean—except me. And I'm standing on the edge of some crazy cliff. What I have to do, I have to catch everybody if they start to go over the cliff—I mean if they're running and they don't look where they're going I have to come out from somewhere and catch them. That's all I'd do all day. I'd just be the catcher in the rye and all. I know it's crazy, but that's the only thing I'd really like to be." —Holden Caufield

The Cricket in Times Square, p. 1960

Author: George Selden

Links to purchase: Amazon Kindle Edition, MacMillan Publishers

Plot summary: The Cricket in Times Square tells the story of Chester Cricket who accidentally ends up in New York City's Times Square after hitching a ride from the country in a picnic basket. After a little boy Mario Bellini catches him and takes him to his family's newsstand, Chester soon befriends Harry Cat and Tucker Mouse. Chester's new friends show him the ropes of the city and discover his extraordinary talent— making music by rubbing his wings together like a tiny violin. 

When the Bellini family faces financial hardship, the three animals hatch a plan to draw more customers to the newsstand. Chester performs concerts, which attract crowds to listen and purchase from the newsstand, revitalizing the Bellini's business. 

My take: The Cricket in Times Square offers a heartwarming tale of unlikely friendships and the magic of music in one of the world's busiest cities. Through the eyes of animals that people often overlook, we get a unique and charming glimpse at New York City. The idea that humans can be moved and inspired by something as simple as a cricket's song is both touching and tear-jerking, reminding us of the power of art and the importance of seeing beauty in the ordinary.  

I get teary-eyed in two places. One, when the whole of Times Square becomes silent to listen to Chester's concert. Two, [spoiler alert] when Chester leaves his friends behind to return to the country. 

"Just this once, in the very heart of the busiest of cities, everyone was perfectly content not to move or hardly to breathe. And for those few minutes, while the song lasted, Times Square was as still as a meadow at evening, with the sun streaming in on the people there and the wind moving among them as if they were only tall blades of grass."

The Color Purple, p. 1982

Author: Alice Walker

Links to purchase: Amazon Kindle Edition, Penguin Random House

Plot summary: The Color Purple follows the life of Celie, a black woman in the early 20th century South. Celie endures several abuse and oppression, as well as decades of separation from her loving sister Nettie. The story is told through a series of letters Celie writes to God. Each letter reveals her struggles with trauma, poverty, and racism in Nettie's absence. Through the support of her friendship with the singer Shug Avery, Celie begins to discover her self-worth and identity, and even recovers pages of letters from Nettie that her husband had hidden over the years. 

My take: The Color Purple is worth reading for its raw, emotional depth and the unique perspective it offers through the epistolary (series of letters) format. The letters to God give us access to Celie's most intimate thoughts and feelings, providing a stark contrast to the silence that smallness that define her outward life. The most poignant and tear-jerking moment of the novel comes when [spoiler alert] Celie is reunited with Nettie after decades apart, along with Celie's children who were taken from her. The moment is a profound moment of healing and reclamation. 

"I think it pisses God off if you walk by the color purple in a field somewhere and don't notice it. People think that pleasing God is all God cares about. But any fool living in the world can see it always trying to please us back." —Shug Avery

Beloved, p. 1987

Author: Toni Morrison

Links to purchase: Amazon Kindle Edition, Penguin Random House

Plot summary: Beloved is a haunting novel that explores the psychological, physical, and emotional scars of slavery in the American South. Set in the Reconstruction period after the Civil War, the story follows Sethe, who'd escaped slavery and who is now haunted by the spirit of her decease daughter, Beloved. The story delves into Sethe's traumatic past, including the painful choice she made to kill her daughter rather than see her recaptured into slavery. As Beloved's presence grows increasingly powerful, Sethe is forced to confront her past and the lingering horrors of slavery. 

My take: Beloved is a must-read for its masterful and multilayered narrative framework and unflinching exploration of the scars slavery leaves. The narrative combines a third-person point-of-view with the perspectives of individual characters, thus offering distinct voices and depth to the subject matter. The close, personal portrayal of the horrors of slavery is a difficult but necessary reading experience if we hope to confront one of the ugliest stains on human history. 

The novel's emotional impact is profound, especially in the moment when Sethe, after everything she's been through, finally embraces herself as her "best thing." 

"Love is or it ain't. Thin love ain't love at all." —Sethe

Atonement, p. 2001

Author: Ian McEwan

Links to purchase: Amazon Kindle Edition, Penguin Random House

Plot summary: Atonement follows the consequences of a young girl's misunderstanding and actions. Set in England before, during and after WWII, this novel begins with thirteen-year-old Briony misinterpreting a moment between her older sister Cecilia and the son of the family servant Robbie. Briony accuses Robbie of rape, an act that sends him to prison and shatters the entire family. The novel then follows the aftermath of Briony's actions and the impact on Robbie and Cecilia, culminating in Briony's efforts to atone for the damage she caused in her youth. 

My take: Atonement is a must-read for its intricate narrative structure and the emotional depth it brings to the story of love, guilt, and the long quest for redemption. Ian McEwan masterfully shifts between different points of view, allowing us to experience the perspectives of the three main characters—Briony, Robbie, and Cecilia—each of whom is profoundly affected by Briony’s tragic mistake. Briony’s first-person narrative in her old age adds a powerful layer of reflection, as she grapples with the lifelong burden of guilt and regret. The novel is deeply moving as it captures the intensity of the love between Robbie and Cecilia, a love that was brutally cut short by Briony’s actions, leaving behind a haunting sense of what could have been. Witnessing Briony’s journey to atone for the irreversible damage she caused is both heartbreaking and poignant, making Atonement a profoundly emotional and unforgettable read.

"How can a novelist achieve atonement when, with her absolute power of deciding outcomes, she is also God? There is no one, no entity or higher form that she can appeal to, or be reconciled with, or that can forgive her. There is nothing outside her. In her imagination she has set the limits and the terms. No atonement for God, or novelists, even if they are atheists. It was always an impossible task, and that was precisely the point. The attempt was all." —Briony Tallis

The Kite Runner, p. 2003

Author: Khaled Hosseini

Links to purchase: Amazon Kindle Edition, Penguin Random House 

Plot summary: The Kite Runner follows the story of Amir, a wealthy boy from Afghanistan, and his complicated relationship with Hassan, the son of the family servant. After a kite-running event in which the two boys participate, Amir witnesses Hassan being brutally raped by Assef, a wealthy and cruel boy, and does nothing to stop it. Years later, Amir escapes war-torn Afghanistan for America but eventually returns to his homeland under Taliban rule. He discovers that Hassan was his half-brother and that Hassan's son, Sohrab, has been taken by a Talib who turns out to be Assef. Amir rescues his nephew and brings him back to the U.S., seeking redemption for his past.

My take: The Kite Runner is a powerful must-read for its exploration of class differences, the consequences of our actions, and the overwhelming weight of guilt that can burden us for decades. This novel offers a masterful exploration of the complex relationship between Amir and Hassan and the responsibility Amir feels for his nephew. The real tear jerker moment comes when Amir witnesses Sohrab's deep trauma and retreat into silence, even after Amir brings him to a secure homelife in the U.S. Despite this, Amir's unwavering resolve to care for Sohrab and help him heal is both heartbreaking and deeply moving, making the novel an unforgettable journey of redemption and hope. 

"Every other sin is a variation of theft. When you kill a man, you steal a life... you steal his wife's right to a husband, rob his children of a father. When you tell a lie, you steal someone's right to the truth. When you cheat, you steal the right to fairness... there is no act more wretched than stealing.” —Baba (Amir's father)

 

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