Most Depressing Goddam Books EVER.

[Eve]

When you're wallowing in bitterness and self-pity, there's no pick-me-up like a good, depressing book. I was lucky enough to find a copy of The Lost Weekend (Charles Jackson, 1944) and am thoroughly enjoying it—it makes the movie version look like a two-reel comedy (and yes, there is a gay subplot).

Other favorite slit-your-wrist reads (both well-written, by masters):

Predestined: A Novel of New York Life (Stephen French Whitman, 1910, reissued 1974), the story of a man who fails, repeatedly, at everything he attempts in life.

Back Street (Fannie Hurst, 1931)—again, if you've seen either of the movies, you won't be prepared for this grimly realistic book about a woman's doomed affair with a married man and how her life is slowly ruined.

What books make you want to turn on the gas?

[MovieMogul]

No book has ever devestated me more than Something Happened by Joseph Heller. Some beautiful passages, but as a whole, it really made me fearful of the life that might lie in store for me (I read it in high school).

[Caricci]

Last Exit to Brooklyn by Hubert Selby, Jr. isn't exactly a book I would recommend to a depressed person. I could totally see it sending someone right over the edge.

[Paul in Qatar]

The Cruel Sea War, suicide, abuse, endless death.

A great read.

[Nonsuch]

A good pulp noir novel can usually make you reach for the scotch and sleeping pills ... They Shoot Horses, Don't They? and The Postman Always Rings Twice are terribly engrossing, and depressing, reads. Sometimes it's fun to wallow in it.

[Spectre of Pithecanthropus]

I nominate most of the apocalyptic sci-fi novels. Most of the good ones have their hopeful moments, but god the basic premise is soooo depressing.

For non-sci-fi, I suggest:

McTeague, by Frank Norris (1899). A stupid great clod of a self-taught San Francisco dentist is caught practicing without a license or degree, having learned his trade only by apprenticeship to an itinerant tooth-puller. This was the time requirements for the professions were becoming formalized. Once he's turned in, he moves through successively more menial jobs, and his standard of living declines accordingly. The story was immortalized in film by Von Stroheim's classic Greed.

Joie de Vivre, by Emile Zola. The title was ironic, right?

It Can't Happen Here, by Sinclair Lewis. Fascists win the 1936 presidential election. It's not considered one of Lewis' best novels, but the idea that such a thing could happen here is definitely scary. The regime breaks down in the end, but it's still depressing...and gripping.

Fatherland, by Robert Harris. It's 1964, and Germany has won WWII, and directly controls all of Eurasia to the Urals. The rest of Europe is mostly subservient to them, with an SS training academy in Oxford. Edward VIII and Queen Wallis reign in England. The Germans are preparing for a state visit from President Kennedy...that's Joseph P., not John F. Pretty grim, but still gripping reading.

[Rufus Xavier]

I went through a period where I read a slew of Jim Thompson books. Yikes! Check out these brief synopses:

The Grifters: A grifter's near-Oedipal relationship with his grifter mother affects his shallow relationship with his grifter girlfriend. Even the people who survive this book are not going to live happily ever after.

A Hell of a Woman: A man kills for a woman, then goes slowly insane. This does not end on an upbeat note. There are no upbeat notes in this chilling book.

The Getaway: Unlike either of the movie adaptations of this novel, the protagonists (who are, in fact, hardened criminals) get away from the law, but end up trapped in a living hell that makes prison seem comparitively attractive.

The list goes on, but you get the idea. Despite the fact that few characters in any Thompson book have redeeming qualities, many are depicted in a way that makes them seem real. You could even identify with them, which makes the ending of each book that much harder to deal with. There are no happy endings.

I highly recommend these books.

[plnnr]

Originally Posted by Rufus Xavier

I went through a period where I read a slew of Jim Thompson books. Yikes! Check out these brief synopses:

The Grifters: A grifter's near-Oedipal relationship with his grifter mother affects his shallow relationship with his grifter girlfriend. Even the people who survive this book are not going to live happily ever after.

Annette Benning in The Grifters...grrrrrwwwwllllll.

Sorry for the hijack.

[Fugazi]

I'm not really into depressing books, so I haven't read many (like 1) but I did read Orwell's 1984. Jeez, what a bring down that book was.

[Ellen Cherry]

It's probably not as depressing as those already mentioned, but I found A Simple Plan by Scott B. Smith to be an enthralling look at how greed can warp ordinary morality and rationality. The book is gripping, too, in how the reader is forced to feel guilty as the conspirators! (At least *I* felt guilty!) I just felt sick and responsible the whole time I was reading it. Fabulous book.

[Dung Beetle]

Originally Posted by Ellen Cherry

It's probably not as depressing as those already mentioned, but I found A Simple Plan by Scott B. Smith to be an enthralling look at how greed can warp ordinary morality and rationality. The book is gripping, too, in how the reader is forced to feel guilty as the conspirators! (At least *I* felt guilty!) I just felt sick and responsible the whole time I was reading it. Fabulous book.

I love this book. Every step of the way, I could say to myself, "Well, yeah, that's probably what I would have done." Damn, I wanted it to work out! But I liked the book so much I wouldn't call it depressing.

My picks:
Grapes of Wrath
1984 (as Fugazi said)
Roadwork by Stephen King
The Nanny Diaries

I felt terrible for days after the Nanny Diaries. I just had to keep saying to myself, "There aren't really people like that. There aren't really kids in families like that." And I know there are!

[DocCathode]

Satan- His Psychotherapy And Cure By Dr Sy Kasller JSPS

With a title like that, I expected comedy. Instead, in the first ten pages Sy manages to enrage his father to the point of cardiac trauma. Sy was simply trying to finally get to know his dad. It goes on like that for the whole book. Every time something good happens to Kassler, it's followed by something horrific. I can't give examples without spoiling the book. But (and none of these events happen in the story.) it goes something like this- 'Hmm. I'm homeless, jobless and unloved. I may as well spend my last dollar on this lottery ticket. I won a hundred million dollars! And look, it's Sarah, the girl I've secretly loved for years but never had the guts to approach. Sarah, will you marry me? Yes! Great, let's walk to city hall. . . . What? Hospital? Car accident? Sarah took the ticket? And she's marrying you, doctor? Why? You amputated my penis and attached it to your own? '

It's a well-written book and there are numerous references to Dante's Inferno (I've considered finally reading Inferno just to get more insight into this book). But it's massively depressing.

[Finagle]

I'd nominate Boys and Girls Together by William Goldman. And most of his other non-thriller novels aren't too upbeat either.

Goldman has pretty much mastered the technique of making you care about his characters and then doing horrible things to them.

[SkipMagic]

Originally Posted by Finagle

I'd nominate Boys and Girls Together by William Goldman. And most of his other non-thriller novels aren't too upbeat either.

Goldman has pretty much mastered the technique of making you care about his characters and then doing horrible things to them.

Damn you. I came in here to nominate that book. But since it's do depressing, I think it's appropriate to nominate it again.

[Treviathan]

Originally Posted by Finagle

Goldman has pretty much mastered the technique of making you care about his characters and then doing horrible things to them.

That's exactly how I would describe Rohinton Mistry's A Fine Balance, about four characters trying to survive under Indira Gandhi's suspension of the Indian constitution. That book really slammed home the hopelessness that must come with living in absolute poverty.

[Mal Adroit]

Originally Posted by Finagle

I'd nominate Boys and Girls Together by William Goldman. And most of his other non-thriller novels aren't too upbeat either.

Thing of It Is ends kinda nicely, doesn't it (two happy people boffing)? Father's Day, Color of Light, The Silent Gondoliers all turn out okay. . . I'd agree with you, though, that he loves to torment his characters.

Would second most of the noir picks, especially Jim Thompson. Criminy, Savage Night ends with all the civility and logic of William Burroughs describing his night sweats.

Mother Night just killed me.
Can't actually remember how J.M. Coetzee's Life and Times of Michael K. ended, but the book was so unrelentingly bleak that I think I was numb by the time I got there.

I don't know, Eve, sometimes I think depressing books actually just make you feel lousy!

[Small Clanger]

Keep the Aspidistra Flying by George (chuckles) Orwell.

A dirt poor bad poet is determined to be an artist and not to give in to "the system". Of course he does in the end. Horribly accurate descriptions of all sorts of English middle class mediocrity. The most miserable happy ending ever.

[Eve]

Originally Posted by Small Clanger

Keep the Aspidistra Flying by George (chuckles) Orwell.

Damn you for making me laugh out loud in this thread!

Nonsuch, I have a collection of such bitter noir novelists as James Cain and Tiffany Thayer—best read in satin lounging pyjamas, with a tea & Vicodin cocktail at one's side.

[Miss Mapp]

House of Mirth by Edith Wharton. It's downhill for Lily Bart all the way.

Actually, just about any Edith Wharton novel is a tad on the depressing side.

[twickster]

I don't want to get all classy on y'all -- but how about Edith Wharton's House of Mirth? Lily Bart, beautiful, well-connected, but poor, ends up with neither her wealthy suitor nor her true love -- after her reputation is sullied*, she ends up killing herself.

*Verb provided by Merriam Webster's Encyclopedia of Literature, whence I retreated because I can never remember whether this or Custom of the Country is the one with the lovely Lily Bart. "Sullied." What a great freakin' word -- and one I don't manage to work into as many conversations as I'd like.

[twickster]

Damn, should have known Miss Mapp would beat me to the punch on Wharton....

[Ukulele Ike]

Originally Posted by Rufus Xavier

The Getaway:....end up trapped in a living hell that makes prison seem comparitively attractive.

Hoo boy, is that an understatement. The Getaway has one of the most chilling denouements I've ever encountered. You never think about barbecue in quite the same way again.

I love the ending of James M. Cain's Double Indemnity, too...again, much more bleak and surreal than the one in the movie.

Jean Rhys' early novel Quartet is another delightful dip into despair.

[Eve]

Originally Posted by Ukulele Ike

Hoo boy, is that an understatement. The Getaway has one of the most chilling denouements I've ever encountered. You never think about barbecue in quite the same way again.

I don't even wanna know . . .

The only reason I don't want to see a remake of Double Indemnity, following the Cain book more closely, is because you'll never get anyone to play Phyllis Dietrichson like Barbara Stanwyck did. Can you imagine her in an uncensored version?