4. The Secret History, by Donna Tartt
The best time to read The Secret History is probably while you’re still in college, because it is about a secret society at a small liberal arts college gone horribly awry, but it is also worth picking up a few years later to be reminded about the intensity of college friendships, and also Ancient Greek.
6. A Visit from the Goon Squad, by Jennifer Egan
These interwoven narratives (some of which were published as stand-alone stories in magazines such as the New Yorker) are brilliantly crafted, wryly tender portraits of life and love and the small tragedies of everyday modern life.
9. The Moviegoer, by Walker Percy
The story of Binx Bolling is kind of like what might have happened if Dick Whitman never became Don Draper, and instead started wandering around first New Orleans, and then the country, on a neverending spiritual and existential quest.
10. White Teeth, by Zadie Smith
In addition to White Teeth being perhaps the ultimate 20th century British immigrant novel, it will also, possibly, inspire you to greatness: Smith finished it during her final year at Cambridge and was 24 (!!!) when it was published.
13. Bright Lights, Big City, by Jay McInerney
You read this book because even though they used typewriters and did way more cocaine than is even remotely healthy, it’s still a perfectly told story about being young and thinking you’re way too smart for what you’re doing. Also it’s possibly the only book ever written in the second person that actually works.
18. The Sun Also Rises, by Ernest Hemingway
Another English syllabus special, Hemingway’s tight prose and peerless storytelling are somehow more resonant when you are reading it on your own. Or as my colleague Matt put it: “I couldn’t keep my eyes open for more than five pages of Hemingway growing up, but for some reason I picked this up in my post-graduation haze and was mesmerized.”
22. The Group, by Mary McCarthy
How is it possible that a novel written in 1963 about a group of post-collegiate friends in New York City IN THE 1930S could still be so relevant? Probably because the struggles of being in your twenties — particularly, how much do you care about the opinions of other people, and what does success mean? — have been the same since the dawn of time.
23. Quicksand and Passing, by Nella Larsen
These two novellas written by a half-black, half-Danish woman in the 1920s capture the complications of that time — sexism and racism chief among them — while also being the beautifully told (and timeless) stories of deeply flawed young women.
24. Pastoralia, by George Saunders
I’ll let my colleague Aylin’s boyfriend explain this pick: “It just illustrates in such a breathtakingly beautiful, memorable way how easy it is for people to inflict pain on each other and how terrible it is to fall between the cracks in America, which it’s easier than ever to do now. I don’t know, I feel like reading it made me feel more compassionate toward people.” Aw!
25. Ready Player One, by Ernest Cline
Says my colleague Krutika: “It’s the perfect mix of childhood nostalgia for anyone who’s in their twenties right now, and futuristic dystopian action/adventure where everyone’s unwittingly more earnest and sincere than they mean to be.”
27. The Bell Jar, by Sylvia Plath
My friend Julia puts it well: “What the protagonist Esther Greenwood goes through pretty much speaks to my whole generation and the next. College graduates who don’t know what they want to do as a career, are not excited about things their parents say they should be, want to have sex but not babies… all of it. It also encourages young people to be unafraid to voice their feelings and opinions. Makes me wish Sylvia Plath could have read her own book without prejudice — it might have helped.”
28. Main Street, by Sinclair Lewis
A book about an ambitious, difficult woman who is forced by circumstance (like being born in the wrong decade, in Minnesota) to keep settling for less than what she wants. But she doesn’t stop trying her hand at finding utopia.
33. I Love Dick, by Chris Kraus
I’ll let my friend Emily handle this one: “Readers will be rewarded with most psychologically astute sex scene ever written, plus a thorough, impassioned and wholly unique analysis of the power dynamics of heterosexual sex and love, how heterosexuality works to keep women unrepresented and unable to fully represent themselves, and how that affects the world.” Whew! (Also, sorta fun to read this one on the subway, IYKWIM.)
35. Even Cowgirls Get the Blues, by Tom Robbins
I love what my friend Evie says about this book: “It is kind of a primer on absurdist literature and speaks volumes to self-doubt and discovery and body image and feminine identity reclamation. Plus, it has that sense of humor that you have in your twenties when you think you are SO FUCKING CLEVER, and sometimes you actually are.”
37. Bossypants, by Tina Fey
This whole book is filled with brilliance — about work, about being a woman, about being a mom, about being a boss — but one of my favorites is what Fey writes about Amy Poehler: “Amy made it clear that she wasn’t there to be cute. She wasn’t there to play wives and girlfriends in the boys’ scenes. She was there to do what she wanted to do and she did not fucking care if you like it.”
41. Lunar Park, by Bret Easton Ellis
Technically a novel, but more of a fictionalized memoir: “It’s about what happens when you reach your career goals yet you still find yourself haunted by ghosts,” says my colleague Michael. Also, it’s important to read Bret Easton Ellis before you get too old.
44. Oh the Glory of it All, by Sean Wilsey
I love what my friend Alex says about this book: “It’s just a fab memoir about growing up in San Francisco, but mostly the dude had a TERRIBLE childhood. And I think terrible childhood books are best for people in their twenties (file under whining, quit yer).” I would also add that it’s a fascinating window into a rarefied S.F. world of non–Silicon Valley wealth, and Wilsey manages the neat trick of making us empathize with him despite his family’s comfortable finances.
50. The Complete Poems of Anne Sexton, by Anne Sexton
Sexton was a revolutionary: She wrote frankly and breathtakingly about incredibly personal and controversial topics — including her mental illness, drug addiction, and abortion — until her suicide in 1973 at age 45.
53. Alien vs. Predator, by Michael Robbins
Michael Robbins is maybe my favorite contemporary poet. Here is a verse from a poem he published on The Awl last year:
Maybe it’s Maybelline. Why can’t you be true?
You re-gifted the VD I wrapped up just for you.
My penis and my brain team up to penis-brain you.
It is now my duty to completely drain you.
ESSAYS THAT WILL MAKE YOU THINK AND/OR LAUGH:
57. My Misspent Youth, by Meghan Daum
The titular essay in this collection was published in 1999 in The New Yorker, when the 29-year-old Daum realized that she was totally, utterly broke and needed to leave New York, and her lament is the timeless one of the upper-middle-class liberal arts college graduate who cannot live in the New York of their fantasies: “I spend money on Martinis and expensive dinners because, as is typical among my species of debtor, I tell myself that Martinis and expensive dinners are the entire point — the point of being young, the point of living in New York City, the point of living.”
58. Slouching Towards Bethlehem, by Joan Didion
The Bible for anyone who’s fancied themselves a writer, ever. Didion has probably said what you wanted to say, and earlier and better.
59. Up in the Old Hotel, by Joseph Mitchell
Mitchell was a New Yorker writer whose essays about the city in the 1930s to the 1960s are each gems of keenly observed daily life. Wherever you live, these will make you look at your everyday surroundings a little differently.
GENERAL LIFE HOW-TOS:
63. Letters to a Young Contrarian, by Christopher Hitchens
However you feel about Hitchens’ work, this little volume is incredibly instructive in teaching you how to write things without giving a shit about what other people think. Or to learn how to just not give a shit about what other people think, generally.
With extra-special thanks for their suggestions to the BuzzFeed editorial staff and my friends Chris, Alex, Shaya, Jess, Emily K., Emily G., Melanie, Carolyn, Kate, Elizabeth, Mary, Evie, Julia, Alia, Abbey, and CK. And my mom!