21 Books to Read for a Good Ugly Cry

Sometimes we just need a good, healthy ugly cry.

Sure, you can listen to Tom Waits or Taylor Swift and cry one out…or pop in The Family Stone or Titanic if you’re feeling blue…but for us bookworms, the list of books practically guaranteed to stimulate an ugly cry is often too long to even consider…

The thing about books is that you spend SO MUCH TIME with these characters.  A sad movie is over and done in a couple hours…but for some of us, a sad book may take months to complete…so it really is an emotional roller coaster to finish some of these stories!

I love a good ugly cry…and I give big props to books that can bring me to tears.  While some of these were more tear-jerking than others, they are all worthy of a read if you’re feeling like you need to open the floodgates a little bit.

21 Books to Read for a Good Ugly Cry

One Day
David Nicholls

A relationship is brought to life over the course of 20 years. Snapshots are revealed on the same day – July 15th – of each year, and as Dex and Em face fights, laughter, tears, and missed opportunities, they must come to grips with the nature of love and life itself.

We Were Liars
E. Lockhart

A group of friends spends a beautiful summer on a private island, laughing, swimming, as socialites do. But when an accident causes a secret to be released, everything changes. This book is slow to start, but the end made it worth it for me.

My Sister’s Keeper
Jodi Picoult

What would you do for the people you love? When Anna is forced to sacrifice her health for the safety of her sister, Kate, questions about life and morality are raised. A provocative novel that raises important ethical issues, this story is about the struggle for survival…at all costs.

Night
Elie Wiesel

Perhaps the most brilliant and heart-breaking book in the Holocaust canon of literature, Night should be required reading for every human being. Honest, eye-opening, and terrifying at times, this memoir puts readers right into the middle of the chaos.

Bottomless Belly Button
Dash Shaw

This graphic novel tells the story of a family that comes together for one weekend, only to discover that the reason for the gathering is that mom and dad are getting divorced. A story for the times, this novel is so truthful, raw, and honest.

The Lovely Bones
Alice Sebold

After Susie Salmon is murdered, she tries to help her family solve the mysteries surrounding her death. Told from Susie’s perspective as she watches the aftermath of her murder unfold from Heaven, this story raises interesting questions about the afterlife, and what that means for those who must continue on surviving.

The Little Prince
Antoine de Saint-Exupery

This timeless tale tells the story of a little boy who leaves the safety of his own tiny planet to travel the universe. Through a collection of extraordinary encounters and discoveries, we learn, along with the Prince, how wonderful and sad life can be.

A Monster Calls
Patrick Ness

Oh man…if you’re only gonna read one book on this list for the ultimate ugly cry, it should be this one. One of the most truthful and beautiful portrayals of what it’s like to loose a loved one to a sickness, this story will utterly wreck you.

Tuesdays with Morrie
Mitch Albom

After Mitch Albom reconnects with his college professor, Morrie Schwartz, at the end of Morrie’s life, a beautiful friendship develops that turns into a collection of final lessons on how to live. You know how this one ends, but it doesn’t make it any easier.

The Year of Magical Thinking
Joan Didion

This memoir explores important questions about life as a widow, a wife, and a mom. When author Joan Didion suddenly looses her husband at the dinner table, she embarks on a journey of anger, healing, and understanding that’s all too familiar if you’ve ever lost a loved one.

The Road
Cormac McCarthy

After the human race is basically obliterated after an unsubscribed apocalypse of some kind, a father and his son must fight for survival in a world that is nearly void of life. This is a quick, but powerful read.

Daytripper
Fabio Moon

How would our lives be different if we waited in the longer line in the grocery store? If we really ended up with our soul mate? If we got our dream job? This graphic novel explores the question that forever plagues the human race: what if? Truly inspiring and bittersweet, this book was one I found myself reading again immediately after finishing it the first time.

The Art of Racing in the Rain
Garth Stein

A heart-wrenching but deeply funny story about family, love, loyalty, and hope, this book is beautifully crafted and is a captivating look at all the wonders and absurdities of human life…as only a dog could tell it.

The Book Thief
Markus Zusak

Set during WWII, this groundbreaking novel tells the story of a girl, Liesel Meminger, and her love of books. Narrated by Death himself, this story raises interesting questions about why and how we die, using the background of the war to better highlight how all walks of life continue to run from the same enemy.

The Last Lecture
Randy Pausch

After his fatal diagnosis of pancreatic cancer, professor Randy Pausch gives his class one last lecture before retiring to spend the rest of his life with his family. This one is a heart-wrencher. Filled with inspiring and motivational quotes, this little book packs a powerful punch.

Love You Forever
Robert Munsch

A short children’s story about a mother and son, this book is probably on the shelf of children all over the US. The deeper message of aging and the circle of life make this book a must for kids (and adults) of all ages.

Revolutionary Road
Richard Yates

I’ve realized that this book is on a lot of book lists that I do, but it’s just that good. As we watch a seemingly perfect marriage fall apart at the seams, it becomes clear that relationships are a lot different to those on the inside, and sometimes what we see is NOT what you get.

Red Hook Road
Ayelet Waldman

This one hit me in a very unexpected way. As a newly married couple drives to their reception, they become victims of a deadly car crash. The families awaiting their arrival are left to pick up the pieces, and go from planning a wedding to planning a funeral.  Now they must learn to work together to honor the wishes of the now deceased bride and groom.

Bridge to Terabithia
Katherine Paterson

OMG. I’m sure we all read this as pre-teens, yes? The ultimate he/she friendship story, this book tells the tale of Jess and Leslie, two friends who create a magical kingdom together where they reign as king and queen, that is until a tragic accident changes everything. OMG WITH THE TISSUES.

To Dance with the White Dog
Terry Kay

This was the first book that ever made me cry!  When Sam Peek’s wife passes away, his children worry that he won’t be able to take care of himself; however, when a mysterious white dog appears, Sam wonders if it’s the spirit of his wife returning to him.

Of Mice and Men
John Steinbeck

A beautiful story about friendship, this classic book hits ya right in the gut. Two outsiders work together to find their place in a society that wants nothing to do with them. A story that has birthed a Broadway play and not one, but THREE acclaimed films, this book is great for a good, classic cry.

Looking for a new book to read? Check in every Friday for a “Bee Happy” post, where I share reviews of books I’ve read or other book-themed lists.