All the Sad Young Literary Men Teacher’s Guide

By Keith Gessen

All the Sad Young Literary Men by Keith Gessen


Questions and Topics for Discussion


All the Sad Young Literary Men is the first novel from Keith Gessen, the Russian-born editor of the literary journal n+1, and a masterwork of wry comic insight. The novel tracks the erratic course of the lives of three young Jewish men coming of age in the unsettling last days of the twentieth century and beyond. Sam is a would-be writer and roustabout who finally finds himself in the tumult of the West Bank; Mark is a graduate student who triumphs over a decade of isolation to emerge a new man; and Keith, a former jock at loose ends with life, finds that in realizing his dreams of literary New York he has left something of himself behind.

All the Sad Young Literary Men is an acute and perceptive portrayal of the lives of the young, ambitious, and overeducated. Gessen takes his title from F. Scott Fitzgerald, and indeed there is something of Fitzgerald’s yearning romanticism and keen eye for the telling cultural detail in Gessen’s characters. All the Sad Young Literary Men features protagonists who are full of anomie and spiritual restlessness, and uncertain of their role in the modern world. Gessen has the ambition and the assuredness to make a statement not just about a set of characters created for this specific narrative but about an entire generation.

Gessen’s book also has immense reserves of humor and goodwill. His temperament is satiric and humanist, and he is much too amused by the foibles and vanities of his feckless creations to wish them any real harm. Among the many beautifully realized ancillary characters—and this is part of Gessen’s gift, how in a few pages his bit players become more vivid and alive than some novelists’ narrators—is a successful, famous writer named Morris Binkel. A ferocious snob, Binkel rages at the inadequacy of the culture, which paralyzes and destroys him. Sam, Mark, and Keith may do foolish, ridiculous, vain, self-defeating things, but in the end of they are of the world, not above it. Being part of the human race, Gessen seems to say, is the price for being part of the human race, and it is a pleasure to be reminded of this with such clarity and wit.



Keith Gessen was born in Russia and raised in Massachusetts. A contributor to The New Yorker, The New York Times Book Review, and New York magazine, Gessen is also a founding editor of the literary magazine n+1. He is the translator of the NBCC Award–winning Voices from Chernobyl and the upcoming Penguin classics edition of Ludmila Petrushevskaya’s Scary Fairy Tales.



Q. Your title takes off from F. Scott Fitzgerald’s collection All the Sad Young Men, published in 1926, a book that became famous for capturing the zeitgeist of the Roaring Twenties. Do you feel your book has a parallel relevance to early-twenty-first-century life?

I wanted it to, yes. And the book has had an interesting reception, I think. Most older (and foreign) people have pretty much accepted it as a report on this part of the world, from this historical time. A British reviewer said it had identified a new, tiny subculture. Younger American reviewers have had the opposite reaction: They’ve said, “This is not us at all!” And maybe it isn’t you. But it was me, more or less; that’s all I’m sure of.

Q. Another famous story from Fitzgerald’s collection is “Winter Dreams,” which deals explicitly with class envy and the lure of social status. The characters in All the Sad Young Literary Men are often conscious of being social and economic outsiders. (“It was 1998 and the rest of the world was rich.”) Is this an intentional echo? Do you regard class consciousness as a central concern of contemporary fiction?

I don’t know enough about contemporary fiction to answer that, but I do know that any human society on any level will begin to segregate along class lines. Put another way: I grew up in a wealthy suburb where I was usually the poorest among my friends and then attended a wealthy university for whose fine class distinctions I had no preparation at all. Objectively speaking I was very lucky to be at these places. My parents worked very hard to give me the opportunity to be there. But there was also a subjective experience involved.

In America right now everyone is worried about money. A lot of people are in danger of losing their homes. The guys in this book have been worried about that for a while.

Q. The past five years have seen a small wave of writers and editors with Soviet-bloc origins: Gary Shteyngart, David Bezmozgis, Aleksandar Hemon. You have translated stories by Vladimir Sorokin and others. Would it be an exaggeration or oversimplification to call this a movement? If so, do you consider yourself part of it?

I admire those writers, but I don’t think we have very much in common.

Q. Popular culture of late—from “grups” to Judd Apatow movies—has been dominated by depictions of men who refuse to accept the traditional responsibilities of adulthood. Is your novel a continuation of this theme or a reaction against it? What are the causes of this phenomenon, if it exists? How does it affect contemporary fiction in general?

That’s an interesting question. I look around me and all I see is people getting married, people working eighty hours a week (those who are still working), people worrying about their future. So as a description of the actual world, those films and articles fail. I think, if anything, what they do is suggest that in fact these men who’ve not accepted “adulthood” are disappearing. Judd Apatow is like the French collaborator Brasillach, who would give out the addresses of Resistance fighters during the Occupation: There is the last forty-year-old virgin! There is the last twenty-five-year-old dude living with his friends! Round ’em up.

This book opens with Mark married and living in Queens. Is he more adult at that point, married at the age of twenty-two, than he is at the end of the book, thirty years old and sitting alone and confused with a big backpack in the Syracuse bus station? I mean, neither turns out to be a terribly enviable situation.

Adulthood is an experience of freedom. It means saying that the life you live is the life you’ve chosen, without apologies to anyone or excuses. The guys in this book are often silly and foolish and sometimes they do things that hurt others, but they’re trying to figure things out. They’re really trying. I think that’s a grown-up and serious thing.

Q. There’s a certain acerbity to your portrayal of academic life. You were an MFA student. Do you have some hostility toward academe? A traditional academic satire like Lucky Jim has a lot of anger. Are some of the more satiric bits in All the Sad Young Literary Men attempts at evening the score in any way?

It’s true, I really can’t stand universities. Which is too bad, because the people I read and admire most, whether fiction writers or sociologists or historians or my old teachers, are academics. I even like academic literature, and I love university libraries. But at some physical level I’m allergic to the university. Maybe this will change as I get older. But for the moment, as Gogol once said, “We spit at each other and parted, the university and I.” It was for the best.

Q. Mark describes his graduate colleague Leslie as “part of the new barbarian horde that liked cultural analyses of tiny objects.” Are you thinking of the slate of recent histories about the pencil, salt, etc.? Do you happen to share Mark’s disdain for this trend? Does it represent the narrowing of the world-critical apparatus to a point of no return? Or is it the logical endpoint for the premises (as Lomaski would say) of deconstructionism?

Well, that’s about right. I think the micro-histories come out of a kind of perverse reading of Foucault. Foucault argued that power was dispersed through society in a million different places, not just the obvious ones that were typically the subject of historical writing: kings, parliaments, the proletariat. So a history of modern Europe could be written as a history of its prisons, or its sexual practices, rather than of its wars and revolutions. I don’t think he ever claimed you could write a history of the world as a history of its pencils. So really the micro-historians have taken Foucault very far! Which is funny, because Foucault took his own private sexual practices very far. He liked to attend the most violent, extreme S&M leather bars in New York and San Francisco. On my book tour I met a man who’d come to Foucault once on one of these tours of the biker bars and dropped out after a day because it was too brutal. Anyway, the micro-historians should do that too.

Although I should add that I don’t really know what’s going on in graduate history departments. I’m more familiar with graduate literature departments, where students can sometimes become extremely focused on tiny things. So I was kind of extrapolating those onto an imaginary history department. I don’t know if anyone’s really writing a history of the staple.

Q. Mark observes that “in Syracuse it was better to stay drunk and drugged, and the Syracuseans knew it.” You got your MFA at Syracuse University. Is Mark’s sentiment a reflection of personal experience?

Syracuse is a tough place to live. They built a highway through it in the 1970s that now separates the university from the downtown. People moved to the suburbs. A lot of American cities are like that.

Q. Keith’s first chapter, “The Vice President’s Daughter,” includes droll little photos of Hegel, Abraham Lincoln, Monica Lewinsky, Keith’s e-mail inbox, and Clinton and Gore. Why did you decide to include these photos? Why include photos in this chapter only?

For me that time—college, the Clinton years, and all the things that happened—really feels iconic in a way that my life before then or since then hasn’t. When the Lewinsky affair broke, I feel like I saw the images—Monica in a beret, the video of them hugging at a rally—before I ever read about what was going on. I think that happens sometimes, when you’re busy, especially when you’re busy in college and can’t be bothered with what’s going on in the world. And that experience is very powerful; it gives things a kind of magic that they never quite lose even once you learn all the tawdry details.

The whole book to some extent, but that chapter in particular, is about confusing your own life with the lives of the great. Or not so much confusing them as not putting them into perspective—that is, not placing the proper psychic barriers between yourself and these people and events. In her novel about Cambridge, Virginia Woolf writes a little sarcastically but also, I think, sympathetically about undergraduates who are convinced they’re the first ones to truly understand Shakespeare. That strikes me as really the perfect way to go through that time of life, believing that these great books were written to please and instruct you, not that you were placed in college to bow down before the great books. And this can extend to everything in your life, this innocence, this immediacy of experience, and eventually it will be a shock to find out that the world isn’t set up that way and doesn’t care about you very much. But that’s later.

So somehow the photos from that time evoke it for me, still, in a very visceral way. I hope they will for others, too. If you were writing about a college student in 2008, the images would have to be different. They would be celebrity images rather than political images. And you would end up with a very different kind of story.

Q. Lauren appears to be based on one of the Gore daughters. Is that true?

Well, in a sense. I did go to the same college as they did, but I didn’t know them. That story is really about what it’s like to get to college and find out where you fit in the world and where you don’t. And how difficult it is to find that out. In terms of the actual events and people in the story, they’re made up.

Q. Sam says that as a Jewish writer “the last thing on earth you wanted was the ADL on your back.” Are you worried about reactions to your portrayal of the occupation of the West Bank? There are probably plenty of people out there capable of playing Gershom Sholem to your Philip Roth.

I actually think the sorts of things you can say with regard to Israel in the United States if you’re a Jewish writer have significantly expanded in the past five or six years. It’s a little hard to prove, but that’s my sense of it. September 11th located Israel in a specific geopolitical context, whereas before it had been more of a kind of mythical place for American Jews. In “Right of Return” I make fun of the declaration made by one editorial writer that “we are all Israelis now,” but that does seem to some extent to have happened. American Jews have become slightly more pragmatic and open about the problems of the Israeli occupation. They’ve become more like Israelis, in that sense.


  • The twenty-year-old Keith finds a hero in Morris Binkel. What does Binkel have that Keith admires? What does that say about Keith’s personality? Years later, Keith fails to defend Binkel’s reputation at a party. Why? How has Keith turned into Binkel? How has he not?

  • The relationships between the three protagonists and the women in their lives are often tumultuous. Do the relationships in the book strike you as authentic? What do the characters value in their counterparts? Does this give insight into the author’s opinion of women?

  • Thinking of his father and his uncle, Keith says, “America was too large; America with its houses, its highways; it had broken them up, and me as well.” How does the size of America break people up? Is Keith referring to it being physically “too large” or to something else? Is there something peculiarly American about this statement itself?

  • Does Sam’s attitude toward Israel and the occupation of the West Bank change as a result of his visit to Jenin? What are his motives for going to Israel? Why does he conceal his Jewish identity from his Palestinian hosts? What does their reaction to his revelation of his identity say about the author’s views?

  • The Jenin chapter comprises a vivid portrayal of Israeli and Palestinian societies, from both points of view. Does the author take sides? In what ways is Sam sympathetic to the Palestinians? In what ways is he not?

  • One of the novel’s comic motifs is Mark’s constant comparison of the unfolding crises in his life to the historical events of the Russian Revolution. He finally decides that “ultimately these historical parallels were of limited use in figuring out your personal life.” In what ways are Mark’s “parallels” deceptions or illusions? Are they ever accurate?

  • The book alternates between accounts of the three characters’ lives. What effect does this narrative device have on the reader? Did you notice that the sequence is not strictly serial? Why is that? Which of the three characters’ narratives did you find the most interesting? Is the tone of authorial voice different from character to character, or is it fundamentally consistent?

  • Keith’s passages are narrated in the first person, while Sam and Mark’s are in the third person. Why? Is it possible that Keith has a different relation, fictionally, to the author? How does the first-person narrative affect your feelings about and perceptions of Keith?

  • In addition, Keith is not mentioned by name until his third chapter, when he reveals his name to Morris Binkel. Why did the author wait so long to provide one of the protagonists’ names? Does it affect the reader’s reaction to Keith? What is significant about Binkel prompting it?

  • Another characteristic of the narrative is that it takes place over a long time, swinging back and forth from the present (2007) to as far back as 199

  • The final chapter is titled “200

  • ” What does this tell you? How do the characters change over the course of the time we know them?

  • Some of the characters overlap very slightly from section to section: Keith ends up with Mark’s former paramour Gwyn; Arielle, who dates both Sam and Keith, ends up with Mark’s roommate Toby; Sam and Mark know each other from college, etc. Why has the author arranged this? At one point Sam says that “no city really is, deep down, all that big.” Are the interconnected relations proof of this? Why or why not?

  • The end of the book, with Keith bounding up the stairs toward his newly pregnant girlfriend, strikes a muted note of ambiguity. Is the ending a sign of newfound maturity on Keith’s part, or are his political preoccupations another sign of evasion? Do his concerns about the future of American and the world strike you as sincere or ironic?
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