The Most Successful Books About Failure for Friday 13th!

orangutan list

Often, we shy away from the concept of failure in books. But for me, failure is the means by which we learn and sometimes a tragic ending can have more of an impact than a happy one. So, I thought I’d share my list of the most successful books about failure. And what better day than unlucky Friday the Thirteenth to discuss it? 😉


Jude the Obscure– Hardy doesn’t pull his punches with this devastating tome. I can’t think of many other books which have left me so utterly eviscerated emotionally.


The Idiot– Dostoevsky often explores the notion of tragedy and failure in his books, but this is my favourite in that vein. Dubbed a failed book about failure, this may not have the most satisfying of conclusions, but it’s very apt for this list.


Hamlet– I needed at least one Shakespearean tragedy on the list and what I like about this one is that it’s an individual tragedy of a man we can (more or less) respect.


The Great Gatsby– Fitzgerald’s masterpiece about the failure of the American Dream explores both the loss of a dream grander scale and a very personal tragedy. What I like is that this book can be read multiple ways- it’s not just society to blame for Gatsby’s ending, but also the individual (bad) choices along the way.

never let me go

Never Let Me Go– a more modern/futuristic tragedy, Never Let Me Go doesn’t just examine the way society can rob us of our futures, but also how we can self-sabotage and waste time along the way. For all its dystopic elements, it is ultimately a very human tale.


Mockingjay– I know that some people didn’t love the ending for Hunger Games, but for me it will always be perfect. Dystopias can’t end too happily and thus (despite some of the more positive aspects of the finale) it delivers the intended message well.

between shades of grey

Between Shades of Grey– the topic of Soviets sending thousands of people to die in Siberia is not talked about enough. This book does a fantastic job of representing this important issue.

the woman in black

Woman in Black– in a very different vein, this thrilling and captivating ghost story actually holds at its heart darker and more unsettling tragedies.

game of thrones book

Game of Thrones- kind of poetic that a lot of people fail in this book given where the show ended up… In all seriousness, this is a significant in the modern fantasy realm because it doesn’t just give us the happily-ever-after good guys triumph over evil we all crave. As hard as it can be to read, we need books that show us a darker reality.


Sadie– I don’t want to spoil anything, so I’ll just say this is more representative of a failure in society than with “The Girls”. A part of why I put this on the list is that I think when true crime is discussed, the victims are often ignored. I think this does a great job of starting to redress that balance. Also, if you want to weep buckets, read this book.

Alright, so have I succeeded or failed with this list? And do you have any books to add? Let me know in the comments!

43 thoughts on “The Most Successful Books About Failure for Friday 13th!

  1. I completely agree; failure can have a much bigger impact than a happy outcome. The Great Gatsby and Never Let Me Go are great examples. I am amongst those who didn’t like Mockingjay, but it wasn’t because of the ending. I actually thought that part was very fitting, it would have been unrealistic with a glossy, happily-ever-after finish.

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  2. To some people happy endings are extremely important, or else they feel disillusioned and a bit depressed. To others the happy ending isn’t vital, as long as the journey takes them somewhere special and helps them expand their mind and soul. Many of the world’s best novels have bad endings. E. M. Forster, in “Aspects of the Novel,” said that nearly every novel’s ending is a letdown. Most of us want extraordinary things, after a while, to quit being extraordinary—to end. The stone fell in the water. The ripples ran. Now they should stop. The surface should be smooth again.

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  3. I do have a minor quibble over Hamlet since he does accomplish his goal, and even makes peace with it in his final soliloquy, when he says “there’s a special providence in the fall of a sparrow”. What about Othello? There’s someone who’s misled by someone he mistakenly trusts, and in the end his crime is that he “loved not wisely but too well”.
    Brave New World also comes to mind, not so much because its protagonists fail but rather because Huxley himself considered the novel a failure, and wrote his last novel, Island, to offer what the earlier novel hadn’t. Alas, though, it makes Island even more of a tragedy.
    On the whole, though, I believe you can call this list a success.


    1. So I do agree that Othello (and basically most of the Shakespearean tragedies) would work for this list- but I don’t agree that Hamlet is a “success”. Yes, he achieves his “goal” of revenge, except the issue is, does he really succeed when the path of revenge leads to his death and the deaths of many others? It’s certainly not a straightforward issue, but that’s part of the reason I chose it. Sometimes it’s more tragic when we succeed at the responsibilities foisted upon us, but fail to get what we really want.
      Brave New World is a good one for this too. I haven’t read the Island yet though, curious about it.

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    1. Jude the Obscure is probably my least favorite novel of all time. I hate that book. Most books I don’t like arouse a combination of apathy or occasionally disgust, Jude the Obscure actually set my teeth on edge. I wanted to tear that book apart by the end.

      I like Hardy’s poetry though.


    2. Well you’re definitely not alone in that! I’ve met so many people over the years who hate it. And I love King Lear too- certainly fits the topic- my choice of Hamlet doesn’t preclude any other Shakespearean tragedy from being suited to the list too!


  4. Dostoevsky is so good. The scene I remember most from The Idiot is the party game where each participant had to tell the story of the worst thing he had ever done. By the time the game was over they all hated each other.

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  5. Orwell’s 1984 is one of the more recent books I’ve read that I would add to this list. Animal Farm could also be included, but I think 1984 fits better.

    I agree that the Hunger Games ending was perfect. It wasn’t a happy ending, but it was a satisfactory one to the reader. There have been other dystopians I’ve read (ie: the later part of the Divergent trilogy) where the ending just wasn’t satisfactory. Sometimes it can feel like the author gets it in their head that “this is a dystopian, so the ending has to be horrible / sad / depressing” and those don’t work for me.

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  6. Great list. I don’t mind failure as long as characters have a chance to either redeem themselves or fix things. What I don’t like is hopeless fiction where the characters are doomed to failure and never have good things happen to them. (Basically I have a huge issue with Steinbeck LOL). 😀

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    1. Thank you! Ah that’s fair- not everyone likes hopeless fiction. Personally, I like it when books trick you into thinking there’s a possibility of a happy ending, even if they foreshadow at the start that there won’t be, but I do get why people don’t like that… or have issues with Steinbeck 😉

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  7. Great post! I agree – reading about failure is honestly so nice, because it shows how we can learn something, and maybe even try to amend past mistakes so we can have a brighter future. Sadie is such a phenomenal book, and I really admire how it shows so much about the victim’s side of the story.

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  8. I never thought of it that way. I guess I feel there’s enough opportunity for failure IRL and I want my books to take me away from that. I will reconsider – thanks for sharing the possibilities.

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