The Joys of Sad Stories


A while back a couple of little girls came into my wife’s library and asked, “Do you have any sad books?” What a great question. There’s a lot to love about sad stories. For one thing, sad stories remind us what really matters to us. We feel sadness at the loss (or else the absence) of things we value.

I don’t suppose they knew it, but the girls who asked my wife for sad stories were looking to affirm the things that mattered most to them by feeling what it would mean not to have them. By looking to enter into another person’s sadness (even a fictional person’s sadness), they were looking to experience their own lives more fully. That’s why I love sad stories.

In children’s fiction, nobody does sadness like Kate DiCamillo. The same ache haunts The Tale of Despereaux, The Miraculous Journey of Edward Tulane, The Magician’s Elephant, and Because of Winn-Dixie (I haven’t read her other novels). In each of those stories, the hurt, the loneliness, and the sadness nourish the souls of characters and readers alike.

There’s a great moment in Edward Tulane in which a grandmother tells an awful fairy tale: a beautiful but self-absorbed princess is turned into a pig and eaten. The granddaughter is shocked at the suddenness and brutality with which the story ends. “No one is living happily ever after,” she complains.

“But answer me this,” the grandmother says. “How can a story end happily if there is no love?”

It’s a great question, and one we needn’t protect our children from. Without love, there is no hope for a happy ending. The good news is that we live in a world that, though broken, is still shot through with love. Every sadness, every hurt is redeemable. Which is why we need not pretend that hurt and sadness don’t exist.

My favorite sad children’s book is The Hundred Dresses, by Eleanor Estes. Wanda Petronski lives on the wrong side of the tracks. She comes to school every day in the same ratty blue dress. She sits in the back corner of the classroom where the rowdy boys sit. But she’s too unsure of herself to be rowdy. The popular girls don’t pay Wanda a lot of attention except for a game they play every morning in the school yard:

“Wanda,” Peggy would say in a most courteous manner, as though she were talking to Miss Mason or to the principal perhaps. “Wanda,” she’d say, giving one of her friends a nudge, “tell us. How many dresses did you say you had hanging up in your closet?”

“A hundred,” said Wanda.

“A hundred!” exclaimed all the girls incredulously, and the little girls would stop playing hopscotch and listen.

Every day she wears the same dress, but every day she claims to have a hundred dresses in her closet, “all lined up”—velvet, silk, every color, every style. The girls’ persistence in tormenting Wanda every morning is matched by Wanda’s persistence in her outlandish sartorial claims—not just a hundred dresses, but fifty shoes, then sixty, plus hats and coats to match.

Eleanor Estes’s portrayal of schoolroom dynamics—especially the not-quite intentional hurts that children do to one another—is spot-on. There is so much sadness in this little eighty-page book, which was first published in 1944. Wanda has no answer for the popular girls whose lives are so easy by comparison—only those face-saving claims that are all the more humiliating for their overt falsehood. A hundred dresses, all lined up.

I have heard forgiveness defined as “The fragrance that the flower leaves on the heel of the one who crushed it.” I could never quite make sense of that idea until I read the end of The Hundred Dresses. Wanda’s generosity toward the girls who have so sweetly bullyragged her is genuinely moving. I hope you’ll get hold of a copy and read it for yourself.

What are your favorite sad stories?

Jonathan Rogers is the author of The Terrible Speed of Mercy, one of the finest biographies of Flannery O’Connor we've ever read. His other books include the Wilderking Trilogy–The Bark of the Bog Owl, The Secret of the Swamp King, and The Way of the Wilderking–as well as The World According to Narnia and a biography of Saint Patrick. He has spent most of his adult life in Nashville, Tennessee, where he and his wife Lou Alice are raising a houseful of robustious children.


  1. Laura Peterson

    Yes! Kate DiCamillo! Well said, Jonathan. The chapter in “Because of Winn-Dixie” where Gloria Dump explains Litmus Lozenges completely blew me away when I first read it. She’s a master. In fact, I’m having trouble thinking of other examples of sad stories that I like because hers are so good….

  2. Kelly

    I am currently reading Jayber Crow for the first time. This morning I came to the end of chapter 11, when he spends a Sunday walking Port William and allowing himself to remember and grieve the loss of his past life there. He closes out by observing:

    “The grief that came to me then was nothing like the grief I had felt for myself alone, at the end of my stay in Lexington. This grief had something in it of generosity, some nearness to joy. In a strange way it added to me what I had lost. I saw that, for me, this country would always be populated with presences and absences, presences of absences, the living and the dead. The world as it is would always be a reminder of the world that was, and of the world that is to come.”

  3. Terry Kreutzkamp

    For many years I read aloud Bridge to Terebithia to my grade 4 students and had a tough time not choking up in quite a few places (and every darn time, year after year – that’s the power of a great story). Another much more recent and a new very favourite book is Wonder by R.J. Palacio.

  4. Rachel

    Oh, Edward Tulane is by far my favorite sad story! I teach third grade in a bilingual school in Mexico and I read it out loud to my students this year, even though I knew the language was too hard and I thought it would probably go over their heads. I simplified some of the language as I read it and my students LOVED it in a way I could not have imagined they would. We had so many good conversations about whether or not love is worth the pain that comes with it, as Edward continues to say he will never love again because of the hurt of loving and losing. Most of my third graders haven’t loved and lost yet (praise God), but they were able to think through what it would mean to lose someone you love and whether the joy of love outweighed that in the end. We were even able to turn it into a discussion of what Christ gave up in order to continue loving us and to demonstrate his love for us. What an important lesson and opening to share the gospel!

  5. Esther O'Reilly

    Where the Red Fern Grows. In a word, as;dlfkjasd;lkjf;alsjdfl;asdlkjsadfidon’tknowwhatmyfeelingsaredoing. But I think I read it… twice?

  6. anna

    Michael Rosen’s Sad Book makes me cry each time I read it (in the library no less) – it’s not ficion, though it’s in the junior fiction section. I recently read Lois Lowry’s The Giver series, and she does a marvellous sad/incomplete/unexplained ending, which I think is also lacking in most literature.

  7. Eowyn

    A Tale of Two Cities, though I’d really have to say that’s a happy-sad book.

    Hamlet is a sad play, but it’s not so much about sadness as despair. Every time I hear the line “there’s a special providence in the fall of a sparrow” I feel so sad that seemingly every character in the play squander their chance of redemption. I do feel that sadness isn’t as effective when not contrasted alongside hope (unlike Tess of the D’Urbervilles, a massive waste of time), and it does have the subtle hope of the entry of Fortinbras at the ending. He’s the only one who forgives.

  8. Heather Ivester

    I confess I was bereft and pretty much inconsolable for a few hours after finishing up John Green’s The Fault in Our Stars — and I only read it because my daughter’s best friend told me he was her favorite author and that was her favorite book. So I had to find out why. Also, anyone with a sister won’t want to miss Cynthia Kadohata’s Kira Kira … and of course there’s Suzanne Collins’ Mockingjay!

    This past week, I’ve felt sad when looking though our shelf of Junie B Jones books … since Barbara Park passed away and won’t be able to make us laugh anymore with a new story.

    I do think a sad story should leave the reader with hope. That makes the reader see he or she isn’t alone in suffering or finding a renewal of joy.

  9. aimee

    I first read Where the Red Ferns Grows as an adult to my kids, and I wondered, where was this book all of my life? The painful stories carry the most truth, it seems.

    The Fault in Our Stars is a favorite of mine now, though my daughter will be older when she reads it because of certain mature situations. But there is courage in these characters, who live with darkness daily, and I bet the main character would say, “Darkness is a side-effect of living.”

    I need to write a whole post on our relationship with Dicamillo’s books, which I now love, but at first we turned away from them because of the hard parts. It’s taken time to realize that we can’t keep the darkness out of our children’s lives by keeping darkness in books off our shelves.

    At Hutchmoot this year, Jeffrey Overstreet, who seems to have grown up in a very protected environment, said he needed those adventurous books to practice at fighting the darkness. I see that for my own 13 year old, who has grown up with a Momma trying to keep out the darkness for her (as a response to my own childhood).

    What is Jane Eyre without the middle and 2nd half of the story (won’t give any spoilers away)?

    I’ll throw out the title The Hawk and the Dove, by Penelope Wilcock, as a book with a joy in the characters that can’t be separated from the sadness. I plan on reading it aloud with my daughters as they get to be 15 or 16.

  10. Sally

    Jonathan — you made me go pull my copy of “The Hundred Dresses” off the shelf and re-read it. It is a great story.

    When I think of sad stories, they usually involved the death of a loved character.

    When I was younger, I read through every horse and dog book I could put my hands on. Books by Walter Farley, Marguerite Henry, Albert Payson Terhune, Jim Kjelgaard, and Jack London were all favorites.

    The two that stand out in my mind, though, are by none of those authors. “The Yearling” — mentioned once or twice on the Rabbit Room — is the first book I really remember grieving. A book along the same lines, “A Day No Pigs Would Die” by Robert Newton Peck, is gritty, violent, and sobering. I don’t regret reading it, and yet I don’t think I would ever recommend to any of my children. It was too much.

    As far as books that make me cry. “The Giving Tree” by Shel Silverstein, and “Love You Forever” by Robert Munsch top the list.

  11. Cara Strickland

    I too love the Hundred Dresses. Such a bittersweet book.
    Although it’s not a children’s book The Elegance of the Hedgehog is one of my favorite sad stories. There was something lingering in that sadness, and that’s what makes a sad story for me: it stays with me for a while, wrapped around me.

  12. Hannah

    None of these are children’s books but: The Chosen, The Promise, My Name Is Asher Lev, The Gift of Asher Lev (all Chaim Potok), How Green Was My Valley (Richard Llewellyn), Cry, the Beloved Country (Alan Paton), Gilead (Marilynne Robinson), The Children of Hurin (J. R. R. Tolkien).

    Haven’t read any Kate DiCamillo. Maybe I’ll look her up over Christmas.

  13. Bethany

    Kate DiCamillo really is brilliant. I loved/hated the Hundred Dresses too. Where the Red Fern Grows traumatized me as a child, but I loved Summer of the Monkeys.

    Some of my favorite beautiful and uplifting sad stories:

    Peter Pan, by J.M. Barrie (read as a parent)
    The Tattooed Potato and Other Clues, by Ellen Raskin
    The Bronze Bow, by Elizabeth George Speare
    Holes, by Louis Sacher
    The Little Prince, by Antoine de St. Exupery
    Walk Two Moons, by Sharon Creech
    Unwind, by Neal Shusterman
    Ender’s Game, by Orson Scott Card
    Till We Have Faces, by C.S. Lewis
    The Doomsday Book, by Connie Willis

  14. Destiny H.

    The sad story is a favorite of mine. I love a good bout of weeping – there is nothing quite as refreshing as having one’s heart shattered to bits.

    I definitely agree with those who mentioned The Bridge to Terrabithia, The Little Prince and especially Peter Pan – these are some of my absolute favorites. Others along this line include George MacDonald’s lovely At The Back of the North Wind, Tuck Everlasting by Natalie Babbitt, and The Homeward Bounders by Diana Wynne Jones. Twin Spica is one of the most nostalgic series I’ve come across so far, balancing perfectly the dreams of the young with the disappointments of earlier generations. I also love the intentionally dreary atmosphere of Lemony Snicket’s A Series of Unfortunate Events, coupled with the Beatrice Letters. Snicket’s intent is comedic, but glimpses of truths are present as well. A Severe Mercy (Sheldon Vanauken) and A Grief Observed (C.S. Lewis) are my biographical/non-fiction choices, while Dostoevsky’s The Idiot and Shusake Endo’s Silence are brilliant novels. Yoko Ogawa’s The Housekeeper and the Professor is an quietly poignant little book as well.

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