Books That Made Me Cry

A lot of books have made me sad or upset me, but there are not actually a lot of books that have made me actually cry. For some reason, a lot of them have come up lately, though, so I took a peek at my Goodreads profile to see just how many books are n my “Made Me Cry” shelf and there are only eleven titles (well, there are twelve, but two of them refer to the same short story). So here they are–the small handful of books that have made me get teary!

Where the Red Fern Grows, by Wilson Rawls

Without a doubt, this was the original book that made me cry. My fifth-grade class assigned this book as in-class reading and I snuck it home to read ahead–and thank goodness, because I can’t imagine the scene that resulted happening surrounded by my classmates.

Where the Red Fern Grows is the story of a boy, Billy, who saves his money to buy himself two hunting dogs: Old Dan and Little Ann. Together, they form a tight-knit group. Unfortunately, danger lurks in the woods where they hunt.

When I got to the ending, I was sitting in some enormous discount shoe store while my mom and sisters shopped. I started crying–and I mean ugly crying. I couldn’t find my mom at first, so I was wandering the store having a full-fledged emotional breakdown. When my mom finally emerged from an aisle looking concerned, she laughed when she realized that I was crying because of a book. But I didn’t stop crying, so she had to grab my sisters and get us out of the store to stop people from staring. To this day, no book has devastated me more.

Wit, by Margaret Edson

I appreciated Wit when I saw it performed with Judith Light in the starring role, but I didn’t feel much of a connection to it. It’s a play about a renowned professor, Vivian Bearing, facing advanced ovarian cancer. She approaches her illness with the same rigorous standards she has approached everything in her life, only to learn that you can’t will cancer away (nor the pain of its treatment) with logic or rationality.

It’s possible that since I was only about 18 when I saw Wit performed, I was either unable or unwilling to properly grapple with the deep questions it asks about life, compassion, and death. I think that’s part of it. But it’s also true that when I stumbled on the play in a Barnes & Noble several years later, I had a much more personal connection to the material. My mother had just finished treatment for advanced breast cancer that should have killed her. That time around, I absorbed everything Wit had to offer–and I had more than a few ugly cries to prove it.

The Things They Carried, by Tim O’Brien

I read the stories in The Things They Carried in a perpetual state of horror and dread. It’s a truly wrenching portrait of the lives of soldiers, the devastation of war, the heavy human cost that comes with fighting, and the lasting impact of war on both society and the humans who act it out.

This book is shocking and raw, but not in ways that feel manipulative or lurid. I’ve wanted to reread it for several years now, but I haven’t yet found the stomach to dive back in.

Close Range: Wyoming Stories, by Annie Proulx

In a curious bit of timing, I began reading Close Range just as news broke that one of its stories, about a pair of gay cowboys, was going to be adapted into a movie. I had read Proulx’s second collection of short stories about Wyoming, Bad Dirt, without realizing that it was something of a sequel, so I was going back to read the original.

You’ve probably guessed that it was Brokeback Mountain that made me cry, and if so, congratulations. It probably helped that at the time I was a closeted man in his early twenties starting to tip-toe around the idea of coming out, but the truth is that this story is both wonderful and devastating in its own right. My personal connection to it certainly helped, though.

Bridge to Terabithia, by Katherine Paterson

This is another book that was assigned in my fifth-grade class. What a sadistic teacher I had! To be honest, I wasn’t even sure I liked this book as I was reading it. It’s about Jess and Leslie forming a deep friendship, totally unaware that tragedy looms in their futures. I didn’t feel a connection to Jess and his athletic ambitions and I remember thinking that Leslie was weird. But when I got to the ending, man did I cry.

All My Puny Sorrows, by Miriam Toews

This is a novel inspired by author Miriam Toews’ relationship with her own sister, a renowned concert pianist who committed suicide. That tells you what is so sad about this book right there, but what makes it even more impactful is the way Toews captures the bonds of sisterhood within a complex story about life, death, and how to help someone who is determined not to live anymore. It also helps that Toews is naturally funny. I laughed and cried–often on the same page.

The Great Believers, by Rebecca Makkai

I was braced for a cry when I picked up this book, which deals with the ripple effect of trauma and grief by telling two stories: one in Chicago in the 1980s, where a gay man witnesses the devastation of his community at the hands of the AIDS epidemic, and the other near present day in Paris, when a woman who was on the periphery of the other narrative takes center stage as she looks for her estranged daughter.

Needless to say, bracing myself did nothing to stop the tears.

The Gifts of the Body, by Rebecca Brown

Rebecca Brown had worked as a home care worker for AIDS patients as they prepared to die in the late 1980s and early 1990s, so this detailed and smartly constructed series of interlocked stories does an excellent job capturing the emotional toll of illness and death on the ill, their families and friends, and on those who care for them. It’s a great and very humane book.

The Heart’s Invisible Furies, by John Boyne

This is another book that made me both laugh and cry, telling the story of Cyril Avery, a gay man coming of age and living in Ireland as it evolves from a sternly Catholic country to something more progressive and open over time. Watching Cyril come out and find his place in the world was a wonderful experience.

The Miraculous Journey of Edward Tulane, by Kate DiCamillo

Yes, this is a children’s book about a porcelain rabbit. Yes, I was an adult when I read it for the first time. And yes, I shed more than a few tears. That’s because this book teaches a wonderful lesson about remaining open to possibility and being vulnerable even though the world has hurt you. It’s also the book I most frequently gift to other people.

There There, by Tommy Orange

Debut novelist Tommy Orange tells the stories of several modern Native Americans as they prepare for a Pow Wow in Oakland. Orange smartly subverts traditional tropes about Natives in America and presents some wonderful portraits of their lives. Even though Orange doesn’t hide that things aren’t going to end well at this Pow Wow, I was surprised by how much it affected me when I got to the end. I think that goes to show how well he crafted his characters. I genuinely cared about them all.

Books That Made Me Cry
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