The 5 saddest books I have ever read

There are books on this list that make me cry every time I read them, books that made me bawl my eyes out the first time but now don’t ever have quite the same effect and books that don’t actually make me cry but are just so melancholy and despondent all the way through that they deserve a place.

This is obviously a very subjective post. Things that make some people cry might leave others cold and I certainly can’t claim to have read every book in the world (though I’ve probably read a larger proportion of the sad ones than the happy ones) but of what I know these are the books that upset me the most.

1.   Brideshead Revisited – Evelyn Waugh

About as melancholy as books come. In all 395 pages I’m not sure there’s a single truly happy moment. I read a large portion of this book on the train and the woman sat opposite me actually asked if I was okay because I looked so miserable.

2.   Harry Potter and the Order of the Phoenix – J K Rowling

And no, not when Sirius dies. That’s just too mainstream for me. I was crying long before that happened. I cried when Harry didn’t like Cho anymore. I don’t know why I was so invested in their relationship but it really affected me. I actually skipped ahead right to the last chapter to see if they got back together, and they didn’t, and I burst into tears. It was the middle of the night (because obviously first read through of a Harry Potter book has to be done in one sitting no matter what time you finished) so I was a little sleep deprived but still, this was not a normal amount of tears. The only reason I can think of was that in the majority of books I read at that age relationships were the be-all and end-all and every relationship you had was The One. But here was Harry thinking Cho was the perfect girl but then realising that actually there was something more important in his life. Or it was because it was 5am and I still hadn’t been to sleep.

3.   A Solitary Blue – Cynthia Voigt

The Tillerman series by Cynthia Voigt is a series of books that really more people should know about. I have mentioned it in an earlier post so I won’t bore you with a full synopsis. In short it follows four siblings who are abandoned by their mother and have to find someone who will take them in. A Solitary Blue is the third story in the series and doesn’t really feature the main characters and really isn’t the best book in the series but boy did it hit me hard. In a scene where the main character reaches the pit of depression and spends a day at a fairground attempting to forget everything wrong in his life I had to put the book down to cry for a good half an hour. You can still see on in the book where the ink ran because the page got so wet. When I’ve reread it it’s never had quite the same effect but I will never forget the impact it had the first time.

4.   Catch-22 – Joseph Heller

I think if I was really pushed to choose I would pick this as the best book ever written. It is such a clever book; witty and cynical and thought provoking. And that almost reveal of ‘Snowden’s secret’ was so powerful. I’ve read this book several times and I still find it a bit hard to follow and I’m not sure I completely understand it but that doesn’t stop me from feeling just how harrowing and close to the bone the events described are.

5.   The Boyfriend List – E Lockhart

I know that the title of this book doesn’t exactly sound like the kind of book that would be hugely unhappy but it really was. It’s told non-sequentially so the reader almost pieces the story together of how the main character’s life fell apart as the book progresses. In the chapter where she recounts how her boyfriend broke up with her the description is kept so matter of fact, without any embellishment of ‘how it felt’, that I just found it heart-breaking. Like what she was feeling couldn’t even be described. And because we’re told right from the beginning that they’re going to break up at some point it has this sense of impending doom hanging over it. Any time I read this book I’ll always burst in to tears as I’m reading that passage. Fortunately large portions of the book are hilarious so you don’t stay sad for long.


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