98 Comments

Where the Red Fern Grows by Wilson Rawls. If you’ve read it, you know. My Dad and I read it together when I was 9 or 10 and it’s one of the few times I saw him cry. I mean like noisy, messy cry. Interestingly my teenage son read it in his literature class two years ago and was sorta “meh” about it. Definitely written in American rural vernacular- not sure it holds up to modern life. But if you want a beautifully written story about a young boy and his dog you won’t find a better one.

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That book GUTTED me!

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Same here; I read it when I was 12 and cried at the end, and I don't even like dogs--I'm a cat person!

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This book was my first true heartbreak as a kid

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It’s always the sad dog stories, isn’t it!

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Same as a kid.

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I have no idea why this is the first thing that comes to my mind since I read it literally 20 years ago but - Harry Potter and the Order of the Phoenix. Sirius Black was a good man!! So sad.

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💔💔💔

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I sobbed at Dobby's death for sure

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Omg same. Heartwrenching

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IKR? Dumbledore’s death was sad and a bit shocking. Also, in the last book, I hated the deaths of Lupin and Nymphadora at the Battle of Hogwarts.

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Omg yes Lupin!!!! That one was horrible :( reliving all the sadness now haha

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Sirius dying was the worst thing that ever happened. My heart 💔💔💔

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One of your tougher questions!

Life After Life by Kate Atkinson made me think about the infinite counterfactual lives we never get to live, a dangerous and wounding subject for someone like me, susceptible to brooding introspection.

Still, I recommend it highly! She pulls it off brilliantly.

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Ernest Hemingway’s A Farewell To Arms was probably the first book I read that really got me tearing up

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This was the one that got me hooked on Hemingway!

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I keep meaning to read that

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Black Beauty. It is the book that had the biggest impact on me and the first novel I had ever read (so I've already used it as an answer once!) However, when it comes to which one hurt the most, it's still this one. I was so young and it made such an impression because of the cruelty to horses and told from the horses perspective I was incredibly sad. I'm sure there are others, but again, this one is stuck in my memory.

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Absolutely agree - I think it was one of the first books that made me sob.

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Same for me. The cruelty stayed with me. I had an even stronger reaction reading it with my daughter.

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COLD MOUNTAIN by CHARLES FRAZIER!!!!! I was SOBBING and inconsolable....just omg

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Same. Ugly crying and I still cry when I watch the movie. Which I seem to need to do very few years.

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Alsoooo The End of Loneliness by Benedict Wells omgggg

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On Earth We’re Briefly Gorgeous!

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I really liked this book and it is absolutely heartbreaking.

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That book was GUT WRENCHING

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Yep! And like Sophie’s Choice, I made it through once and that’ll do!

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Yes! So beautiful and so hard to read as well at times.

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I've had a look at the description and it sounds both intriguing and heart-rending

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The saddest book I have read is "Beloved". But the book that hurt me the most was " Lord of the Flies". The degradation of human nature left me feeling hopeless and helpless.

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Thank you for reminding me of this one: "Lord of the Flies" tore me up at age 11.

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Young Mungo by Douglas Stuart. Heart = totally ripped out

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Omg how did I not know that Douglas Stuart had written another novel? Loved Shuggie Bain, must add this to my list!!!

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Hahaha I don’t know?! It came out last year - one of my absolute favourite books I’ve read this year (might even be THE favourite book of my year). I loved Shuggie Bain too, but imo Young Mungo is even better! And honestly, even sadder. If you loved Shuggie you’d like this too xxx

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Becoming a Man by Paul Monette. I'd only come out a few years before reading this book and the thing I most wanted in the world was a relationship.

So reading the story of a man who actually had a relationship, only to then lose his partner to AIDS, was utterly gut-wrenching for me. Much of the reason for that I think -- beyond the inhererent tragedy that was the AIDS epidemic -- was Becoming a Man was the first time I had read about two men in a loving relationship. To read that such a thing was possible, only to have it end in such awfulness, left me devastated.

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You’re going to laugh at me but The Left Hand of Darkness. When they’re out on the ice floe, I still pause when thinking of it. And then they turned it into a postage stamp.

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For me it's Larry McMurtry's 'Lonesome Dove'. Parts of it just tore me to shreds but I couldn't put it down. I know for a fact I'll never read it again.

Pat Conroy's 'The Prince of Tides' comes a close second.

I read 'The Diary of Ann Frank' when I was a teenager, and I think it must have been the reason I became an activist. Devastating because I knew the outcome.

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Norman Mailer's HARLOT'S GHOST. It's his paranoid could maybe be true history of the CIA novel. It has the best opening 100 pages I've ever read. It's over 1,000 pages long. The last three words are "to be continued..." And then that bastard went on to write some other completely unrelated novels. And then he died. I always knew he was an asshole. I'm still pissed off decades later.

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If we're talking about hurt as in intellectual injury I believe that "The Suffering Channel" by DFW is my choice (Not a book but a very long short story from "Oblivion"). It's quite grotesque and doesn't refrain from painting the most horrible pictures in your mind. Dude committed suicide 4 years afterwards so...it's quite dark yeah.

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That one really stayed with me as well.

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It’s Zoo Station: the Story of Christiane F. for me. The book is a story about a 13/14 year old girl and her addiction to heroine and prostitution. I read it when I was the same age and it had quite an impact on me. Probably the reason why I never touched any drugs apart from alcohol and caffeine.

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Definitely, without a doubt, Where the Red Fern Grows. Devastating.

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Never Let Me Go by Kazuo Ishiguro. I was bawling, I don't think I've ever cried that hard from a book. Devastating. Also Trust Exercise by Susan Choi. It's not billed as a horror novel but I found it to be one of the most horrifying books I've ever read, just the endless cycles of violence

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Ah! Devastating. And yes, I cried too. When think of the book I still tear up & it’s been 17 years since I’ve read it.

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This is much on my mind, as I recently interviewed Kao Kalia Yang about her forthcoming memoir, in which she tells the story of her mother's life. I would have said that Kalia's first book, The Latehomecomer, hurt me most. But her new book, Where Rivers Part, cuts even deeper. Such lyrical yet heartbreaking writing about the Hmong experience.

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Thanks for sharing this Joshua. I didn't know that Kao Kalia Yang had a new memoir coming out. I loved The Latehomecomer and recommend it to people often.

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Glad to know that I'm not alone in admiring her work. I'll be publishing the first installment of our conversation about her new book first thing tomorrow. That excerpt will be free, so maybe you'd enjoy a peek at the new memoir?

https://joshuadolezal.substack.com/

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Wow. Perfect! Thanks Joshua.

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Der Struwwelpeter ("shock-headed Peter"), which is a German children’s book from 1845. It hurt me because I didn’t like finishing my dinner and the book illiterates, literally, how not finishing your dinner leads directly to death. Highly recommend checking it out.

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Oh god, I was absolutely TERRIFIED of that book

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three men in a boat

when i was 16 or maybe 17 i've heard of a writer called jerome k jerome. so i got a book called 3 men in a boat. but the book was printed with an error: 43 pages missing! i got to page 57 (never forget) all good, funny. page 58 was marked 58 but on it was printed page 14, on 59 - page 15, on 60 - page 16 and so on. on page 100 was printed page 100. 43 pages missing! hurt me so much that i never finished the book, never tried to find a proper copy.

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This sounds very Calvino-ish: If on a winter's night a traveller

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That's an incredible book.

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I agree, though I have to admit I haven't finished it yet. I came across the plan calvino drew up to work it all out. It did my head in

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I'm even more impressed with him now, knowing there was a plan. I loved that book so much, but it did take some time for my brain to recover (maybe it never has)!

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I know, it's pretty mind-frying!

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loved three men in a boat! hope you find a proper copy!

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Diary of a Young Girl by Anne Frank still haunts me... reread it with my daughter as it was her middle school assignment and I could barely hold it together.

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I read Little Fires Everywhere in the early post-partum period with my first born baby girl. I picked it up before there was screen adaptation buzz so I had no idea what it would be about until I was sucked totally in. The varied portraits of motherhood and what it means to come of age as a woman in that book gutted me

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A Little Life by Yanagihara. Went into the book blind. Could have used a trigger warning from the person that recommended it😳

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Love this book. Had the same experience but somehow better that way, going in blind

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The Watsons Go to Birmingham-1963 by Christopher Paul Curtis. I was ten when I first read it, and also when I first heard of the Birmingham bombings. It didn't make me cry, but hearing about children dying that were younger than me was a lot to process at that age. Mind you, this was months before 9/11 happened.

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I am way more sensitive in midlife so when doesn't something hurt me is more the question! But you never forget your first: Charlotte's Web. I cried and cried over Charlotte's death (spoilers!) then happy tears for her children. It's a complex ending for a child.

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I had never read it until I read it aloud to my son. Lots of tears from both of us.

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Glad you had each other for hugs. Children's books have such a deep range of emotion. It's only in rereading the ones I loved that I've noticed how deep, and felt both as a child and an adult.

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Most recently, the euthanasia roller coaster chapter in How High We Go in the Dark by Sequoia Nagamatsu. In the Dream House by Carmen Maria Machado and Salvage the Bones by Jesmyn Ward got me bad too.

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the euthanasia roller coaster definitely stayed with me as well!

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We read so many hurtful books in primary/grade school... There were several, but one that viscerally stuck with me was, "On My Honor", and another later in life was "A Thousand Splendid Suns." OOF.

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I don’t understand why our children in USA are exposed to so many hurtful books i n primary school. Books about locked-in syndrome, drowning, kids dying. When I’d read these books with my son it felt like there is a rush to take my child’s innocence away. I feel it turned him off from reading.

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The Bible hurt my rassclot feelings - no lie.

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Black Beauty.

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Oh my god yes - I was weeping 😭

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Giovanni’s Room by James Baldwin.

The language was so gorgeous it hurt. Everything about the book destroyed me -- the internalised homophobia of the main protagonist and the way it wrecked havoc in the book. Baldwin is able to evoke such a storm of emotions in such an exquisite way. I hated this book with all my heart because it HURT.

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Nov 8, 2023
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I KNOW RIGHT!! It’s nuts how anyone can write so beautifully -- the entire book felt like I was being kicked in the gut. There was a few scenes in the end in which I felt my heart was going to jump out of my throat because it could not bear the pain.

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Thanks for the shoutout! And I've been mulling over this question. If it's the hurt that a great literary work can inspire on the part of characters, I'd say Toni Morrison's "Beloved." That's a book I've been meaning to re-read for years, but it really did cut deep the first time around. With a book that's hurt me because of wrong assumptions or needless cruelty, that's more complicated. I'm still not sure about that.

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Beloved for me is the greatest book ever written about despair and desperation.

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Maybe Humboldt’s Gift by Saul Bellow. Don’t remember plot details, but Humboldt’s figure, that genius, the self-destructive poet, being the hero of the book although he’s dead - I do recall the strong impression it made on me. Bellow in general is the writer that has moved me most, and deepest. And then, just a few years ago, I discovered someone coming close to him, in his tradition of profoundly human, shattering, crushing: Jonathan Safran Foer (his novel called Here I Am).

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I think for me it has to be Ian McEwan's The Comfort of Strangers. I thought it was grotesque, and it actually gave me nightmares for a couple of nights. In other words, it hurt me mentally by disturbing my equilibrium. Its only saving grace is that the storyline, in my opinion, is utterly preposterous. Apologies to any McEwan fans reading this but that's how it is. I reviewed it in a somewhat tongue-in-cheek way if anyone is interested: https://open.substack.com/pub/terryfreedman/p/review-the-comfort-of-strangers-238?r=18suih&utm_campaign=post&utm_medium=web

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Little Women when Beth dies gutted me as a child when I finally realized what was happening.

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The Quran. I witnessed a lot of gruesome things because of it at a personal level, but also from studying history. September 11 taught me even more than I wanted to know.

Communist Manifesto. I spent too much of my life working in former communist countries and heard too many firsthand accounts of the oppression and barbarity in those places. I also saw the environmental destruction that resulted from communist regimes.

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I'm with the "sticks and stones may break your bones" crowd.

I don't know how a book could 'hurt' me. The idea sounds a little woke Gen Z-ish to me.

I could tell you what captivated me the most, what shocked me the most, what affected me the most but hurt??? I have pass on that question

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The Green Mile by Stephen King made me ugly cry. Even more affecting than the film adaptation I would have said.

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No Longer Human by Osamu Dazai.

It's a deeply internal look at someone basically picking themselves apart and looking at their pathetic life in retrospect, and it hit so close to home it completely crushed me for a while. I don't know if I'll ever find a character I relate to more than Yozo Oba, the main character (minus his intense misogyny, that part of him was hard to swallow).

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The God of Small Things by Arundhati Roy, devestating

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I loved this book, but oh so sad. The way she was able to use the written word to create a sort of score to the book is unlike anything I’ve ever seen before.

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Good way of putting it. One of the most beautiful, effective, and gutting books I’ve read.

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Seeing Voices was my first book about hearing loss... I remember the feeling.

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This is a hard question for me. I think the most recent book that hit me where it hurts was the book

The Shack by William Young.

Having once been a big fan of Stephen King, ( I found that I was becoming a bit too paranoid so I stopped reading his books after The Stand) was in Cujo. The movie version sanitized the books actual end where the child dies from heat exhaustion. Sorry for the spoiler alert. I’m a total sap anyway so it doesn’t require monumental works to get me teary eyed. I really enjoyed the other comments though as well as your essay.

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My recent one was Damnation Spring by Ash Davidson. Absolutely gorgeous and gut-wrenching.

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So many! but I think the latest one is Lonely Castle in the Mirror by Mizuki Tsujimura

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A Lesson Before Dying by Ernest Gaines. Even when it was obvious there would be no reprieve, I couldn’t help hoping and found myself sobbing at the end.

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As a young adult, most of Melina Marchetta's books! (highly recommend)

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Gone With the Wind. I couldn't really "root" for any character from a moral standpoint, but that book absolutely wrecked me. I am still not okay. Besides the emotional upheaval I went through, it's also so well-written.

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The final Clan of the Cave Bear books. Waited nearly 20 years for the last two, and they were awful. Final one in particular was a painful, painful read.

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Thank you so much for the recommendation!

Books that hurt me, hmmm. I stay away from horror or grotesque stuff because my imagination is too vivid. I suppose Richard Dawkins, because in his books hje says things that are untrue. He causes harm to young people, and that makes me angry.

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Oh. I just thought of one book. Watership Down. Rabid warrior rabbits.

If you want movies, Psycho. I still have trouble with shower curtains.

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To this day, remembering Norwegian Wood by Haruki Murakami makes me bawl. I spent three feverish days lost in that book, and when it ended, it felt like I ended with it. Absolutely devastating, and devastatingly beautiful.

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