1. The Emperor’s Children, by Claire Messud
The best 9/11 novel that’s much more than a 9/11 novel. Weirdly relatable, even though the characters are all pretty much upper-class pseudo-intellectuals.
2. What She Saw…, by Lucinda Rosenfeld
Important twenties life lesson: Dating losers is not a life sentence. (Thank god.)
3. The Deptford Trilogy, by Robertson Davies
A wondrously insane and magical (in that it is actually about a magician) three-book series.
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.
5. Giovanni’s Room, by James Baldwin
A timeless story of masculinity, desire, and heartbreak that has become particularly resonant for young gay men.
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.
7. The Brief Wondrous Life of Oscar Wao, by Junot Díaz
A book about the search for meaning even when life might be meaningless. (Also, my colleague Ariane says: “Yunior is also the dopest narrator you will ever encounter.”)
8. Lucy, by Jamaica Kincaid
A powerful coming-of-age story of an introspective 19-year-old girl from the West Indies who becomes an au pair in the U.S.
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.
11. The Amazing Adventures of Kavalier and Clay, by Michael Chabon
Jews, New York, World War II, superheroes, comics, Nazis, love: It’s all here, in spades. One of the leading contenders for Great American Novel status.
12. Infinite Jest, by David Foster Wallace
Because you’ll never have time to read it later.
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.
14. The Namesake, by Jhumpa Lahiri
A beautifully told coming-of-age story that is also about how to reconcile in-betweenness: of culture, of place, of time.
15. Call Me by Your Name, by André Aciman
Says my friend Chris: “Super-duper gay sexy but also gorgeous.”
16. The Rachel Papers, by Martin Amis
The Rachel Papers is “a fairly essential ‘leaving adolescence and discovering that everything is still confusing and awful’ kind of novel,” says my colleague Jack, which seems like a pretty decent recommendation.
17. Song of Solomon, by Toni Morrison
You almost definitely read this in high school English class, but you will almost definitely also have a much different perspective on Milkman and his family and their struggles a few years later.
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.”
19. Never Let Me Go, by Kazuo Ishiguro
The ultimate dystopian love story. If it doesn’t make you cry, your heart may be made of stone.
20. A Home at the End of the World, by Michael Cunningham
A classic “queer Bildungsroman,” as my colleague Kevin says.
21. The Sandman Series, by Neil Gaiman
Gaiman’s dark, tragic comic series originally ran as a 10-book series from 1989 to 1996 but has now entered the graphic-novel pantheon.
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.”
26. A Heartbreaking Work of Staggering Genius, by Dave Eggers
The title is astonishingly accurate, but also, Eggers’ work is a terrific window into what one of my friends calls “MTV lit.” (This is not pejorative.)
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.
29. His Dark Materials trilogy, by Philip Pullman
The classic fantasy series — if you’ve only seen The Golden Compass, the film based on the first book in the series, you owe it to yourself to read the books (which are so much better).
30. Generation X, by Douglas Coupland
To understand where everyone a little older than you is coming from.
31. The Fortress of Solitude, by Jonathan Lethem
About comics and superheroes and coming of age in a nearly unrecognizable Brooklyn.
32. Housekeeping, by Marilynne Robinson
An important book to read to learn about being lonely.
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.)
34. On the Road, by Jack Kerouac
So that you’ll realize the way you felt about this book in high school has totally changed.
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.”
36. Hard-Boiled Wonderland and the End of the World, by Haruki Murakami
Two complicated, brilliant, and intertwined yet distinct narratives (Hard-Boiled Wonderland and The End of the World) about a surreal dystopia.
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.”
38. Kitchen Confidential, by Anthony Bourdain
Will immediately quash your fantasies of opening your own restaurant unless you are a masochist, in which case this book will be your how-to.
39. How to Lose Friends and Alienate People, by Toby Young
Young’s memoir about his (mis)adventures in the New York media scene can seem a bit petulant, but he does manage to capture pretty perfectly that world’s bizarre rituals and petty status obsessions.
40. The Dirt, by Mötley Crüe and Neil Strauss
You think your twenties were wild? HAHAHAHAHAHAHAHA.
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.
42. Just Kids, by Patti Smith
One of my favorite books of the last few years, maybe ever. Smith’s memoir is about falling in love — with a man, with New York, with her adult self — and will make you long for a New York that you never knew.
43. Another Bullshit Night in Suck City, by Nick Flynn
For learning that trauma is traumatic.
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.
45. I Don’t Care About Your Band, by Julie Klausner
These hilarious interconnected essays about finding and losing (mostly losing) love as a twentysomething in New York City take place in the recent past, but something tells me they are timeless.
46. Wild, by Cheryl Strayed
For how, and why, to be brave. And also how to hike for over 1,000 miles alone after your mother’s death, your divorce, and your recovery from a bit of a heroin addiction.
47. Lit, by Mary Karr
Karr’s memoir about her alcoholism is like a punch in the gut, in the best possible way. And as my friend Jess says, this book “will teach you to be honest with yourself.”
48. I’m with the Band, by Pamela Des Barres
Des Barres spent much of the ’60s as a rock ‘n’ roll groupie, and this classic memoir is a good reminder that a narcissist by any other name (aka rock star) is still a narcissist.
49. Dear Diary, by Lesley Arfin
Arfin revisits her funny, dark diary entries from the ages of 12 through 25. There’s lots to relate to here, and also some deeply cautionary tales.
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.
51. Actual Air, by David Berman
You may know Berman best as the lead singer of the Silver Jews, but in 1999 he published a slyly sweet book of poetry that takes on everything from Abraham Lincoln to his ex-girlfriend.
52. The Collected Poems of Kenneth Koch, by Kenneth Koch
For fans of Frank O’Hara who are ready for something a little more exuberant.
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.
54. The Collected Poems of Audre Lord, by Audre Lord
Audre Lorde called herself a “black, lesbian, mother, warrior, and poet,” and her poems — about race, sexuality, love, loss, parenthood, politics, and death — are emotional and angry and warm all at once.
ESSAYS THAT WILL MAKE YOU THINK AND/OR LAUGH:
55. Me Talk Pretty One Day, by David Sedaris
Because it’s sometimes instructive to realize that your awkward, quirky upbringing can become the stuff of best-selling essays.
56. How to Be a Woman, by Caitlin Moran
Moran’s book is a sharp, wise, and, most of all, hilarious exploration of modern-day womanhood, feminism, and being generally kick-ass. (Also, this Tumblr.)
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:
60. How to Cook Everything, by Mark Bittman
No task — whether making pasta or scrambling an egg — is too basic for this book of basics, and sometimes you really need to start with the basics.
61. How’s Your Drink?, by Eric Felten
As my colleague Ray says, “You gotta learn how to drink like a person sooner or later.”
62. The Elements of Style, by Strunk & White
To know how to write.
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.
64. Drawing on the Right Side of the Brain, by Betty Edwards
My colleague Summer says that this book is “so great for creativity in general and encouraging everyone to draw like they did as children.” (And not just for lefties!)
65. He’s Just Not That Into You, by Greg Behrendt and Liz Tuccillo
Because sometimes clichés are true, and it’s important to figure out when.
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!