The Mysteries of Pittsburgh , Michael Chabon
In Chabon’s very first novel, which he began while he himself was just a 21-year old student at the University of Pittsburgh, is the story of Art Bechstein’s last-ditch attempt at a free summer before his mob boss of a father forces him to go into some respectable profession. Meeting an increasingly attractive gay man, a smart-as-a-whip biker, and a flimsy young woman, Art watches as his world both collapses and springs up around him.
Cosmos , Witold Gombrowicz
When Witold and Fuks, two young men living and working in Warsaw, come across a sparrow deliberately hanged in a tree, they are stunned. They begin to examine their world in a fervor, looking for answers everywhere, as young men tend to do — in snatches of overheard conversation, in a line on the ceiling — as they try to track down the dear sparrow’s killer. Existential, angsty, rambunctious, and Polish — what more could you ask for?
Leaving the Atocha Station , Ben Lerner
Ben Lerner’s debut has garnered a lot of hype this year, and with good reason: almost impossibly, this self-absorbed tale about a young poet’s year of study abroad in Madrid is a wonderful, captivating read. Lerner manages to evoke the feeling of being alone in a foreign country — especially of being alone in one whose language you barely speak — better than any other account we’ve ever read. And what else are your 20s about than learning to be alone?
Jesus’ Son , Denis Johnson
Johnson’s chaotic book of connected short stories, all following the exploits of a string of very troubled young men (or perhaps just one) in rural America. If that weren’t enough, this could make the list for the simple fact that this gorgeous, filthy collection is a mainstay on the bookshelves of literary 20-somethings everywhere — so if you want to be able to relate to your angsty quarterlife peers, you might venture a peek inside.
The Graduate , Charles Webb
You all know what this book is about — after all, you’ve seen the movie. Webb wrote the original novel just after he himself had graduated from Williams College. His protagonist, lost after his own graduation and readying himself for a lifetime of “bumming around,” dallies with an older lady before pinning his future hopes on her charming daughter. Fun fact: Webb was disdainful of the attention the Academy Award-winning film version brought to his novel, and didn’t receive any royalties from the film, because he felt it undermined his status as a serious writer. Such angst!
You Shall Know Our Velocity! , Dave Eggers
Eggers’s first novel after A Heartbreaking Work of Staggering Genius (which would also qualify for this list) is about two friends who travel around the world giving out money after one comes by a large sum he feels he didn’t really earn. The novel is a satisfying snapshot of the young man’s mind: filled with harebrained schemes, feelings of confusion, lack of direction and general unease. Sigh.
The Secret History , Donna Tartt
Though the six classics students in Tartt’s murderous campus novel may not all be quite in their twenties, the trope still applies. After all, the novel is just as much about what happens after you go on a Bacchanalian rampage and murder a bystander or two — you know, that part where you’re trying to figure out what the hell just happened and/or get your life back together. That part is important, and you should try to get it right.
Popular Hits of the Showa Era , Ryu Murakami
In this wickedly funny short novel, a group of listless 20-something slackers battles a troupe of bad-ass elderly ladies for the rights to their neighborhood streets. The increasingly bloody and surreal turf war careens into an irreverent, hilarious satire about modern society and the ever-present tensions between both the sexes and the ages. Let’s just hope your twenties aren’t as macabre as this — if they are, you can pick up tips, but if they aren’t, you might feel a little better safe and sound in your apartment.
A Portrait of the Artist as a Young Man , James Joyce
This literary classic depicts the the formative years of Joyce’s fictional alter-ego Stephen Dedalus as he begins to question the worldview in which he has been raised, eventually running off to become an artist as a thousand young college students moan, “If only!” Don’t worry — with any luck, one day you too will be the subject and/or author of one of the meatiest, most well-loved novels in English literature.
On the Road , Jack Kerouac
Kerouac’s semi-autobiographical wander-novel, written when he was just 29 himself, is one of the all-time classics of this genre. The stream-of consciousness Beat bible follows two free-spirited youths as they trek across the country looking for adventure and enlightenment, an impulse (whether realized or not) that we think is pretty ubiquitous for those roaring twenties. Just make sure to bring some comfortable shoes.