Announcement: I READ A LOT.
Now that that little-known fact is out of the way, I’ll begin. I think about this a lot (morbid much?), moments in books that really devastated me (readers, you understand). Of course, the #1 Devastating Moment is when an adored character dies. This is a highly incomplete list, since you probably don’t have all day. Needless to say, here be spoilers. I’m putting the title of the book in bold before I talk about it, so if you haven’t read it and plan to, you can skip to the next book. If there’s a good story of my acute emotional trauma that goes along with that death, I’ll throw it in there.
A disclaimer before I begin: this is going to look like I read mostly male authors, which is actually not true. BUT. I actually started Googling dead female literary characters, sans success. I turned the search to just literary heroines, etc.– surely I was forgetting somebody big? I mean, Anna Karenina and Emma Bovary, sure, but they’re not top 10 material. And you know what I learned? Most female characters either A) kick butt, take names, and live, B) are as invisible as the curtains, and if they die, they didn’t make an impression in the first place– and die the same way. Most actually fit A. So it’s the menfolk who are dropping left and right. Make of that what you will.
LOOK HOMEWARD, ANGEL– Thomas Wolfe
First, I love the Charlie Parker murder mystery series by John Connolly.  His gay hitmen Angel and Louis (not the central characters) alone make them worth reading. In the most recent novel, Angel is hanging out in a (real!) Asheville used bookstore, spying on a contract killer. He’s reading the Max Perkins bio (put that on your reading list) and grumbling to himself about how Perkins (who shortened Wolfe’s novel tremendously) could have done everybody a favor by chopping more out of Angel. I beg to differ, but people do seem to have polarized reactions to this one.
However, if you do read it and do not fall into a heap when Ben dies, then you’re not human. PERIOD. I read this novel for the first time when I was in college. I was sitting on the library steps, reading at lunchtime. I got to the death scene and folded over in tears. A professor (from the English department) I knew well walked up to me and asked, with some concern, what was wrong. I waved the book limply in the air and said, “Ben.” A shadow crossed his face, and he simply said, “Oh. I understand,” patted my shoulder, and let me be.
We can believe in the nothingness of life, we can believe in the nothingness of death and of life after death– but who can believe in the nothingness of Ben?
Much later, I toured Old Country Home in Asheville, the actual boarding house that is the (fictionalized– loosely) setting for Angel. I was with a fellow Wolfe-fanatic, and with us on the tour were, well, I have to say it: two Yankees (who hadn’t read the book). When we got to Ben’s bedroom (i.e., the bedroom where Wolfe’s actual brother died), the two of us shed some tears. The guide looked at us sympathetically and remarked that this was “a difficult room for many people.” The two of Northern extraction asked if there were any good restaurants. I’ll just leave that there. 
One final Wolfe story: this is my favorite teaching story, the moment I felt best about teaching. I had a C-range student who spoke up sometimes, not often, and mostly just did the work: a nice guy, but definitely not at all interested in novels. I was filling in some spare time at the end of the semester with short stories and such, and I photocopied the opening (Part One: 1) of Angel, which is sort of a historical meditation about how Southern-ness evolved. He stopped me after class that day and told me that, in his whole life, he’d never read anything that meant that much to him or that he felt really helped him understood who he was.
MY AWESOME PLACE: THE AUTOBIOGRAPHY OF CHERYL B– CHERYL BURKE
So this one isn’t exactly famous, but thanks to the über-wonderful Topside Press, it has been published. Cheryl B was an explosive character with a destructive side, but she was a brilliant spoken word artist (best know in New York City’s East Village in the 1990s). She eventually disentangled herself from the substance abuse that had marked her life and met fellow queer artist Kelli Dunham in 2004. In 2010, she learned she had terminal cancer, and she died in 2011. It’s really hard to summarize this autobiography: all I can really say is you need to read it. Needless to say, she doesn’t write her own death scene; that’s in the afterword, written by Kelli Dunham, who prefaces it with Cheryl’s own jottings on her forthcoming death (surprisingly accepting and witty). Dunham (a standup comic) doesn’t do dirges; she writes of the death as it happened, but she doesn’t bog down and dwell. Overall, it’s like watching a bright light flicker out unexpectedly.
“A PERFECT DAY FOR BANANAFISH”– J.D. SALINGER
Yes, I read the new Salinger bio. I knew he was creepy-pervey before, and now I know he was ultra-pervey. I choose to separate works from authors. And I also don’t believe this particular story has anything to do with pedophile tendencies. Discuss in comments.
Anyway. Like any good super-angsty teenager who believes she is 100% alienated, I read tons of Salinger and idealized the Glass family (actually, I still do idolize them). Seymour was a great hero, a sage. I wasn’t a big short story fan at the time, so I blew through the novels first and saved Nine Stories until last. Of course, the novels allude to Seymour’s death, but it’s not really “real” until it happens in “A Perfect Day for Bananafish.”
HEDDA GABLER– HENRIK IBSEN
I just really, really like Hedda (please refrain from armchair psychoanalysis). When you see the play performed, and she fires the pistol out toward the audience, that’s the best.
A FAREWELL TO ARMS– ERNEST HEMINGWAY
Catherine, Catherine. This is another one I read as a teenager, one I located a battered copy of in my parents’ house. As a disclaimer, it had no dust jacket, and I was young enough really not to know that she dies. So, surprise!
I’m sure it’s vastly politically incorrect to like this one. Deal. Gore Vidal (how I love him: find him being snarky on YouTube for hours of entertainment for, er, odd people) said: “… a work of ambition, in which can be seen the beginning of the careful, artful, immaculate idiocy of tone that since has marked … [Hemingway’s] prose.” Burn.
And if you’ve ever wondered the source of the famous “alone, in the rain” quotations, it’s this novel: “After a while I went out and left the hospital and walked back to the hotel in the rain.”
“And you’ll always love me won’t you?”
“And the rain won’t make any difference?”
“No.”— that’s your Valentine’s Day gift
Tangentially related story: My brother is probably the only person demanding Hemingway be abridged. He read For whom the Bell Tolls in high school, and his succinct remark was to point out the novel could have been really short if they had just blown up the bridge and quit talking about it. That Hemingway, always wordy.
FRIED GREEN TOMATOES AT THE WHISTLE STOP CAFÉ– FANNIE FLAGG
(book, not movie– I haven’t seen it because I heard how they twisted the plot around so much)
When Ruth died and Idgie was left alone– seriously, how is that not heartbreaking? And yes, the decline of the café that then occurs is not very subtle symbolism. I don’t care. It’s still heartbreaking. Angel and Ireland, Ruth and Idgie– love is not forever, people. Happy miserable Valentine’s Day.
THE DANISH GIRL– DAVID EBERSHOFF
Well, it’s based on a true story; if you can get your hands on the original (out-of-print) biography Man into Woman, it’s equally heartbreaking. Ebershoff’s prose is beautiful, and the multiple “transitions” (including the ultimate one towards death) are engrossing, mesmerizing, and, in the end, tragic.
ALL THE KING’S MEN– ROBERT PENN WARREN
Two-for-one here, because I love me an existential hero TM.
The obvious one is Willie Stark. Even once he sheds his idealism, I continue to admire him for his struggles with authentic/inauthentic existence. He sounds like a down-at-the-heels Camus. When he gets shot, it’s because of a final failure to take responsibility; we in philosophy would term this an “existential smackdown.” When Sugar Boy leans over the mortally wounded Boss and asks him if it “hurts much,” it just rips at you: it’s all the pain of existence.
#2 is Cass Mastern (that’s my favorite chapter of the book). Cass Mastern is the true existential hero of the novel, and for that reason I regard that chapter as the novel’s centerpiece (interestingly, when someone I know taught it, she told students that if they had to skip one chapter, to skip that one– I disagree violently and contend this is cutting out the heart of the novel).
Cass Mastern lived for a few years and in that time he learned that the world is all of one piece. He learned that the world is like an enormous spider web and if you touch it, however lightly, at any point, the vibration ripples to the remotest perimeter and the drowsy spider feels the tingle and is drowsy no more but springs out to fling the gossamer coils about you who have touched the web and then inject the black, numbing poison under your hide. It does not matter whether or not you meant to brush the web of things. Your happy foot or your gay wing may have brushed it ever so lightly, but what happens always happens and there is the spider, bearded black and with his great faceted eyes glittering like mirrors in the sun, or like God’s eye, and the fangs dripping.
Jack, of course, does not understand this until the novel’s end. And I’m going to quote that, too, because it is so damn beautiful.
We shall come back, no doubt, to walk down the Row and watch young people on the tennis courts by the clump of mimosas and walk down the beach by the bay, where the driving floats lift gently in the sun, and on out to the pine grove, where the needles thick on the ground will deaden the football so that we shall move among trees as soundlessly as smoke. But that will be a long time from now, and soon now we shall go out of the house and go into the convulsion of the world, out of history into history and the awful responsibility of Time.
There are significant odds you’ve heard me mention the awful responsibility of time.
INFINITE JEST– DAVID FOSTER WALLACE
Another polarizing author here. I saw somewhere– somewhere I’d never be able to track down– someone commenting that they hated both Brent Easton Ellis and DFW on principle because they both had three names. Well then. (and maybe we should take an honorary pause here to pour one out for all the dead of American Psycho, even though I don’t care for that novel)
This is going to be a weird one, anyway, because it’s about Don Gately: technically, at the “end” (how many sets of scare quotes would do the word “end” justice here?), he’s (maybe?) comatose in a hospital, having vivid hallucinations. Wallace himself said that the end of the novel isn’t actually in the novel; it’s “somewhere beyond the right frame.” I interpret this to mean that what I say, goes. Nyah.
Many of the (many) characters of Infinite Jest aren’t lovable and cuddly; Gately pretty much comes closest. And there he is, dreaming of Linda McCarthy singing.
THE PRIME OF MISS JEAN BRODIE– MURIEL SPARK
Screw you, Sandy.
THE EXECUTIONER’S SONG– NORMAN MAILER
Another politically incorrect one, yep. I didn’t promise you a rose garden. You get Gary Gilmore instead.
This will be used at my commitment hearing, but: this is the novel I often reread when I’m at a very black point. See again: existential hero.
“Well, Vern, Gary said, “I want to show you. I’ve already shown you how I live”– he gave his most mocking smile– “and I’d like to show you how I can die.”
Then the Warden said, “Do you have anything you’d like to say?” and Gary looked up at the ceiling and hesitated, then said, “Let’s do it.” That was it. The most pronounced amount of courage, Vern decided, he’d ever seen, no quaver, no throatiness, right down the line.
(Those are technically Gilmore’s next-to-last words; Mailer does accurately record his final ones, but he buries them– a nice literary trick)
At any rate, in spite of being a spree killer etc., in Mailer’s depiction, Gilmore’s homespun existential philosophy (and being-unto-death) actually inspires me.
THE LORDS OF DISCIPLINE– PAT CONROY
I read this at home. I was sitting in a chair, and my mother was also in the room. So I’m reading quietly . . . reading quietly . . . and suddenly I shoot bolt upright and yell, “PIG!” My mother said, “Now I know exactly where you are.” 
He was ruled by the tyranny of instinct, by passion and the instant legislation of a simple heart.
I went to a school that was an arch-rival of [the school Conroy is thinly veiling]. When my school played against them in sports, our side chanted: “West Point rejects!” 
THE SOUND AND THE FURY– WILLIAM FAULKNER
Quentin, Quentin, Quentin. If loving your sister is wrong, he doesn’t want to be right. I feel like there’s a song in there somewhere.
Honeysuckle was the saddest odor of all, I think.
I now always think of that when I think of honeysuckle.
And screw you, Jason. I’m making a list here.
GIOVANNI’S ROOM– JAMES BALDWIN
More existential fun! But seriously, this is one helluva sad novel. No happiness for anyone, ever, ever, amen. This is what happens when you hide behind straight white American male privilege. #takenote
LITTLE WOMEN– LOUISA MAY ALCOTT
Straight-up lie there. This, I distinctly remember, was the first book I ever didn’t finish. I felt horribly guilty and actually asked my mother if it was okay not to finish a book. I loathed it. I thought it was amazingly drippy.
That said, I knew (maybe the back of the book said something about it? I don’t remember) that Beth died. I flipped ahead to find the scene where that happened, hoping for something good ‘n’ gory. If memory serves, her sewing needle gets heavy, and she “passes into the valley of the shadow of death” or something similar. Gag. I do remember I was very disappointed. Children are bloodthirsty little monsters.
AND THE BAND PLAYED ON– RANDY SHILTS
Everybody. Just: everybody. 
THEIR EYES WERE WATCHING GOD– ZORA NEALE HURSTON
Joe. This is also a super-disturbing death– the circumstances of this death are hard to forget. Janie’s triumph makes this novel a winner, especially since she manages to make her life a success within a specific socio-economic circumstance (not the same one that Joe brought her up to, though “rising” is certainly contextual here). Her autobiography (as she chose to tell it) is actually my favorite work of hers.
They sat in company with the others . . . They seemed to be staring at the dark, but their eyes were watching God.
MEMOIRS OF HADRIAN– MARGUERITE YOURCENAR
Not the world’s easiest, breeziest read, but so good. The whole thing is a letter from the dying Hadrian to Marcus Aurelius. It’s brilliant beyond words, a stunning blend of fiction and philosophy.
BONJOUR, TRISTESSE– FRANÇOISE SAGAN
Well, it’s called “Hello, Sadness,” so what are you expecting? The depths of scheming in a very short novel are painfully human; it’s more or less about a sacrifice. Oh, and she wrote this when she was 19. No pressure.
A PRAYER FOR OWEN MEANY– JOHN IRVING
Oh, man. I almost forgot this one, novel of so much uncontrolled sobbing.  And at least with this one, I know I’m not alone. “O God—please bring him back! I shall keep asking You.” This is probably one of my favorite so-called spiritual novels.
If you care about something you have to protect it – If you’re lucky enough to find a way of life you love, you have to find the courage to live it.
My life is a reading list.
I am doomed to remember a boy with a wrecked voice. Not because of his voice, or because he was the smallest person I ever knew, or even because he was the instrument of my mother’s death, but because he is the reason I believe in God. I am a Christian because of Owen Meany. 
This is one of the few instances in fiction where someone can declare “I am a Christian” and not gain any corniness points: not that it’s corny to profess faith, but that it’s hard to do so in a manner that’s relatable and doesn’t sound saccharine. This novel pulls that off. 
I could go on (and on), but I’m calling it quits. I’d love to hear your favorites (or intense dislikes).
IN CLOSING, A VIDEO:
So why read depressing stuff where people die left and right? This week’s Dear A.E. column has the answer! Specifically, I’m referring to A.E. Housman’s poem “Terence, this is stupid stuff” (LXII), from A Shropshire Lad (1896). It’s a comic poem with multitudes of memorable lines; Housman contends that exposing yourself to the ills of the world will prepare you for them when they really do strike.
Here’s my reading of it:
 See also his incredibly smart and funny Samuel Johnson books. They’re YA, but very adult-friendly.
 Actually, no, I won’t. To quote another novel in this post, The Lords of Discipline: “It’s impossible to explain to a Yankee what `tacky’ is. They simply have no word for it up north, but my God, do they ever need one.”
 This is NOT the same in the movie. Pig’s end is changed completely (a lot of things are). If you’re reading this and thinking of the movie, I understand your confusion.
 Of course, the other popular cheer was as follows: “F-U one time! F-U two times! F-U all the time!” Um.
 Honorary mention to The Mayor of Castro Street, also by Shilts. Honestly, though, it’s not all that well-written. 
 Another note here re: that time period/AIDS activism: I feel like I need to mention Sarah Schulman, because she’s incredible and has written (and produced other media) extensively about that time period, even if she doesn’t exactly fit in the actual subject of this post. See: My American History: Lesbian and Gay Life During the Reagan/Bush Years, Stagestruck: Theater, AIDS, and the Marketing of Gay America, People in Trouble (which, as many, many, many people have pointed out, is the novel that Rent was plagiarized from– except Rent notably sticks with the heterosexual plot elements, which is probably why you’ve heard of it and not Schulman’s novel), and United in Anger: A History of ACT UP (documentary).
 I don’t cry all the time, at every book. Much of this crying refers to reading books as a high-strung teenager with mega-angst. I’m still high-strung with mega-angst, but I’ve refined the emotional outburst bit.
 Owen Meany’s name is clearly a reference to The Tin Drum and to Father Time’s murder-suicide note in Tess. Father Time would have made this list, but I was trying to keep things to the 20th century for the sake of containment.
 For the record, I also think that Russell’s Why I Am Not a Christian is a bit juvenile.