05/06/2014 11:08 am ET | Updated May 06, 2014

The 18 Most Hipster Books Of All Time

Melville House

#HipsterBooks was trending on Twitter last week thanks to a flurry of riffs on classic book titles: Remembrance of Things Pabst, A Farewell to Non-Inked Arms, He's Just Not That Into Your Vinyl Collection.

All puns aside, we got to thinking about which books are commonly enjoyed by the younger, trendier counterculture. It's easy to make jokes about hipsters, which is exactly why we will. But it's also interesting to examine the commonalities these stories share, and why these books resonate so strongly with contemporary readers.

"Hipster" has a nebulous definition, maybe intentionally so. A quick skim through the index of the n+1 book, What Was the Hipster?, which highlights words and phrases such as Bike: fixed gear, Midwestern sensibilities, ironic, gentrification, twee, and cafe, can help to piece together a semi-lucid image.

The book also mentions Richard Florida's The Rise of the Creative Class, a 10-year-old sociological study that predicted a flocking of talented, creative types to more urban areas, leading to a culture that greatly values diversity and sustainability. Sound familiar?

So if a hipster is a talented, socially conscientious creative type who sometimes struggles with sincerity, what's a hipster book? Some common elements include:

  • Pastiche. It's been argued that hipsterdom is the end of original culture, and that our current subculture borrows from various elements of preexisting ones. Whether or not this has any truth to it is debatable, but it's not uncommon for hip books to borrow titles and themes from celebrated classics.
  • Inaccessibility. Lengthy novels with equally lengthy footnotes.
  • Experimentation. A counterculture is tasked with challenging the norm, so it makes sense that books popular among hipsters would be about bizarre or fantastical topics.
  • Existential crisis. The titles that tend toward the realistic rather than the postmodern are generally about a disgruntled protagonist in his or her late 20s, wandering aimlessly and thinking about said aimless wanderings.

Without further ado, we present to you our very definitive list of the 18 most hipster books of all time. These books are so hipster, you probably haven't even heard of them yet!! But actually, you probably have, and you've probably loved them, and they've probably even made you weep, and you've probably carried them with you on the train so as to seem on-trend.

A Heartbreaking Work of Staggering Genius by Dave Eggers:
Eggers's memoir about the death of his parents is a tragic story with peppered-in elements of fantasy. It's a remarkably smart book, but is sometimes dismissed as maudlin. Eggers is also the founder of McSweeney's, a fantastic publisher and site that's designed to look antiquated. Kind of like those suspenders you bought from American Apparel.

No One Belongs Here More Than You by Miranda July:
Like Eggers's above mentioned book, July's short story collection is an incredible exploration of the fantasies we use to cope with pain and tragedy. But, in July's case, said pain and tragedy is moreso the result of a youthful existential crisis spurred by things like breakups or less-than-ideal jobs. It's as inventive as her films and her performance art, but something about seeing her philosophies written out imbues them with tenderness. The most powerful story in the collection, "Something That Needs Nothing," begins, humorously: "In an ideal world, we would have been orphans. We felt like orphans and we felt deserving of the pity that orphans get, but embarrassingly enough, we had parents." The characters proceed to wander around, and Lena Dunham-like circumstances ensue.

Eeeee Eee Eeee: A Novel by Tao Lin:
When it comes to selecting one of Tao Lin's novels as "definitively the most hipsterish," we're spoiled for choice. If we could, we'd pick his series of hamster drawings, but unfortunately they've yet to be compiled into a book. His most recent novel, Taipei, follows protagonist Paul around Brooklyn and through a number of botched almost-relationships, so it was a clear contender. However, the fact that it was published by industry juggernaut Penguin Random House and not Lin's previous, independent publisher makes it slightly less "definitively the most hipsterish" than, say, Eeeee Eee Eeee: A Novel, which is mostly about dolphins, Elijah Wood, and Domino's Pizza.

Infinite Jest by David Foster Wallace:
The most notoriously unapproachable of Wallace's books (it's heavy, literally and figuratively), Jest has an entire movement dedicated to reading it: Infinite Summer. It's been called a book for "endurance bibliophiles," so it's not exactly accessible, especially considering that much of it is comprised of long, convoluted footnotes. In case you're aware of the book but haven't gotten around to finishing it, it mostly involves a corporate-fuddled super state and Wallace's token wordplay.