What's The Saddest Book You've Ever Read?

Illustration for article titled What's The Saddest Book You've Ever Read?

Reading an incredibly sad book is a peculiar experience — you're mad at the writer for making you feel this way, but at the same time you're hooked on each tear-jerking page. Habitual readers know this masochistic feeling well, and most reserve a special, melancholy place in their hearts for the saddest books they've ever read.


I think of this place as a weatherbeaten bookshelf inside an abandoned house. This house has broken windows, and the wind is blowing all through the rooms and ruffling the white curtains gone yellow with age. Maybe the house is on a beach, an empty beach with pale sand and waves lapping weakly under a cloudy sky. Maybe there is a single dog on the beach, a lonely hungry black dog who comes loping towards you hoping to be fed, but you didn't bring any food with you because you came to see what's on the bookshelf.

So. Flavorwire assembled one such bookshelf, constrained by a few rules (no YA, no animal deaths). Their list has some solid choices (god yes, Who Will Run the Frog Hospital?) and some I disagree with (something about the way Atonement is written makes it not that sad to me). But here's my shelf:

  • The Heart Is A Lonely Hunter. This is one where my mom warned me it was going to be sad, and sometimes she says something is sad and I end up being like, "Whatever, Mom, I'm tough." But THIALH slayed me — I think because I read it when I was a teenage girl, and it involves a teenage girl who doesn't get to realize her dreams. Also, both this book and McCullers's The Member of the Wedding project this sense that adolescence cannot end well, which is a really sad thing for a teenager to read, and also scary.
  • The Remains of the Day. This one my dad told me was going to be super-sad. And I think it is way sadder than Never Let Me Go, which made Flavorwire's list. NLMG is all about (spoiler! spoiler!) kids who have to give up their organs and die, which is obviously sad, but TROTD is just about a butler with a pretty cushy life who doesn't die or anything. Instead he just loses his one chance to ever experience true love, and you know he will be really quiet about it for the rest of his life and almost certainly never mention it to anyone, because he does not talk about his feelings ever, which is kind of what got him into this situation in the first place. Sad.
  • Infinite Jest. A lot of parts of this book are funny, or absurd, and I could do without some of the sections about the spy in drag, but it's also one of the saddest books I've ever read because in this book a teenage kid is really, really lonely and it is sort of his parents' fault and sort of not and things are probably not going to get better. Feeling like the author probably had personal experience with this — as well as with the book's more overtly sad sections about a severely depressed woman — just makes it even sadder.
  • The Road. I'm with Flavorwire on this one. I feel sort of bad giving away the end, even though you've probably already read it, and I just gave away the plot of Never Let Me Go, but maybe it's an indicator of this novel's hold over me that I kind of want to respect its privacy. I'll just say that it ends on an almost-deserted beach, and come to think of it so does Infinite Jest, and that's probably why my sad-shelf house is on the beach of my brain. So yeah, tip for would-be sad-makers: deserted beach.
  • Flowers for Algernon. Jesus Christ, never make me read this book again. Seriously, just kill me.
  • Required Reading: 10 Devastatingly Sad Books [Flavorwire]
  • Image via Graeme Dawes/Shutterstock.com



The Red Tent by Anita Diamant. Though I come from an agnostic background, and know very little of the Bible, this book blew me away.

Told from the perspective of Dinah from the book of Genesis (I believe), the author takes scripture and turns it on its head. The perspective the author lends to women of that time is amazing, and I cry every time I read it (yeah, I read it again once in a while, to remind myself how lucky I am to live in 2011).