On the Road
Jack Kerouac
1959, Viking Compass
This is Kerouac’s completely enchanting chronicle of a young adulthood spent fascinated with the “mad to live” individuals he encounters during his explorations, whom he glorifies as creative saints. There’s a sense of melancholy in Kerouac’s language that hints at the “forlorn rags of growing old,” but he and his friends are fully delving into the highs of being young. Kerouac sought not only adventure, but also the unknown, mysterious, and wild aspects of humanity. His soulful and exhilarating account is a testament to the emotional and spiritual foundation of the Beat generation, always searching the universe for answers. On the Road is Kerouac’s everlasting quest to dig life and get his kicks, but also to uncover the holiness of being on a journey. –Dylan

Blue Highways: A Journey Into America
William Least Heat-Moon
1983, Little, Brown and Company

I tried reading On the Road half a dozen times in high school. It was a classic, a favorite–required reading for any self-respecting weirdo or punk. I knew I was supposed to love it, but I didn’t even like it, and I couldn’t quite figure out why until years later, when I read The Sex Revolts, and it talked about how no female character in the book speaks, how all the women have their words and actions filtered through the dudes in the story. On the Road is heavy bromance, and living in a patriarchy is enough of that for me. Those boys unleashing themselves on the world was not my dream of liberation. So it was my great pleasure a few years ago to come upon Blue Highways, a travelogue about getting lost deep in America that connected deeply and squarely with my feelings. It starts with a heartbreak: author William Least Heat-Moon gets dumped and decides he is going to drive around the country with his dog in a van, but only on what he calls the “blue highways”–back roads, essentially–rather than the interstate, with its chains and swift procession. He wanted to see small towns as they remained. He was taking this trip in 1979, the twilight of an era, just before Ronald Reagan would take office and bring about a huge cultural shift for the country, wherein life changed for the worse for a lot of poor people and women. Heat-Moon riffs big on this sense of a bygone America, sometimes with nostalgia, but just as often not. A scholar of early American history, he stops in places whose import has long been forgotten, tells the amazing and strange life stories of the people he meets along the way, talks about landscapes, recounts his boredom and loneliness, quotes Whitman. He’s utterly un-macho and vulnerable, in love with the world and saddened by it all the same. He’s an incredible writer, and this book makes you want to go out and get lost and meet people and eat pie and mourn an America you will never know. –Jessica

Michelle Tea
2000, Seal Press

There are tons of books out there that I feel are highly charged, influential, and even occasionally dangerous for someone to read in their late teens and early 20s. On the Road is one. Ayn Rand’s The Fountainhead and Atlas Shrugged are two more. Books like these can give you the catalyst you need to start something and shape the path of your life FOREVER. Valencia by Michelle Tea falls deliciously into this same category. Michelle Tea is sometimes thought of as the Jack Kerouac of lesbians, but she is her own thing, and it is good. This is a memoir that chronicles one year in the author’s life when she lived in the Mission District in San Francisco in the ’90s and, oh my god, is it interesting. She does drugs, she falls in love with girls so hard it hurts, she works as a prostitute, she drinks and smokes and cries and has lots and lots of sex, and it’s all told in this wonderful, rambling stream-of-consciousness that is so real, so vivid, SO ALIVE that you finish reading the book and want to throw it down and sell all your shit and move to San Francisco to live the life of a broke queer punk girl IMMEDIATELY. Reading Valencia is like inhaling Michelle Tea, and you are going to like it. –Krista

Lunch Poems
Frank O’Hara
1964, City Lights

Frank O’Hara was a New York School poet who made the glib claim that he cared more about art and movies than he did about poetry. He worked a desk job at the MoMA and went walking around New York City writing poems on his lunch break, often on slips of napkins or the backs of receipts. He was gregarious and charming, dated men, flirted with women, drank chocolate malts, had hundreds of friends, was loved by everyone, died tragically at the age of 40 in a car accident on Fire Island, and wrote poems that are so compulsively readable that they almost seem sloppy until you realize how brilliantly he elevated the unstable, ordinary minutia of everyday life to a thing of beauty. How radical he was to allow poetry to be about absolutely anything, whether it was stopping for a liver-sausage sandwich, coughing at the movies, feeding pennies to peanut machines, reading French symbolist poetry, going to Kenneth Koch’s house for the weekend, liking Herman Melville more than Henry James, being in love, smelling fish in Lisbon, smoking too much, feeling gloomy, or simply feeling happy to be alive. The next time you can’t get out of bed, read his poem, “Poem [Lana Turner has collapsed!]” which ends with “there is no snow in Hollywood / there is no rain in California / I have been to lots of parties / and acted perfectly disgraceful / but I never actually collapsed / oh Lana Turner we love you get up.” Keep Frank O’Hara’s spirit close to you as you go through your day. Get up, play hooky, go exploring, watch a film in the afternoon, meet your friends for dinner, laugh more loudly and more frequently than anyone else, kiss boys, kiss girls, flirt with everyone, talk effusively about the art and music you love, spend your last dollar on something frivolous, and then climb into bed at the end of the night, breathless, buzzing, and eager for more. –Jenny

Love Medicine
Louise Erdrich
1984, Holt, Rinehart, and Winston

I’ve read this book so many times I’ve lost count. The prose is gorgeous and the characters are perfectly rendered—I feel I know them as well as they will let me. The novel is made up of linked stories, each told by a different narrator connected to either the Kashpaw or Lamartine families, all of them Chippewa, from the Turtle Mountain Indian Reservation in North Dakota. This is one of those sweeping, multigenerational stories where you piece together family history–the love triangles, the affairs, the running away, and the homecomings–like a puzzle. All together it is a portrait of real American life. While the stories paint a larger picture, they also stand alone. The one I re-read most constantly is “The Red Convertible,” a tale of two brothers and the fabulous times they had before one of them is drafted into the Vietnam War. –Stephanie

Assassination Vacation
Sarah Vowell
2005, Simon & Schuster

They should make posters of Sarah Vowell’s face and hang them in every social studies and history classroom in America with the caption “She makes leaning fun!” Because she does. I know embarrassingly little about American history (seriously, no quizzes, please), but this book made me feel like a smarty-pants. Vowell takes a road trip to places where presidents and politicians were murdered. Doesn’t that sound like fun? She is hilarious, and so smart, and the book will make you feel like you could go on Jeopardy. –Emma S.

A Wild Sheep Chase
Haruki Murakami
1989, Vintage

The nameless narrator of this surreal mystery is tasked with finding a sheep with a star-shaped birthmark on its back and the ability to possess humans. This peculiar quest takes the narrator and his girlfriend from Tokyo to the island of Hokkaido. Along the way, they encounter a slew of odd characters, including a “sheep man” who wears a full sheepskin pulled over his head and several people who’ve had the elusive sheep enter their bodies. This novel is fascinating, but I’ll be honest with you, it isn’t an easy read. It reminds me of a David Lynch movie, because at times it can be difficult to fully grasp what’s happening (there’s an entire chapter about a whale penis). However, by the end of it, you’re like, “I don’t know what the hell I just experienced, but it was really cool.” The reader’s attempt at unearthing some deeper meaning in the story parallels the narrator’s search for the sheep. If you like strange, labyrinthine tales, or if you’re an aspiring fiction writer who’s interested in unconventional storytelling, you have to check out this book immediately. –Amber

Road to Nowhere
Christopher Pike
1993, Archway

This book by legendary teen thriller author Christopher Pike creeps under your skin and haunts you for days. The tagline on the front cover is “Death came along for the ride,” so right off the bat, you know Pike isn’t playing around. The chilling story begins with Teresa, a distraught 18-year-old, running away from home. She gets into her car, not knowing where she’s headed, but determined to leave Los Angeles. While driving up the coast, she picks up two young hitchhikers: a guy named Freedom Jack and a girl named Poppy Corn. Like so many of the page-turners Pike wrote in the ’90s, this one is totally absorbing, full of mystery and twists, and straight up bonkers. But it’s also a poignant exploration of life and death. If you aren’t already addicted to Pike’s work, then you will be after reading this. –Amber

Into the Wild
Jon Krakauer
1997, First Anchor

Jon Krakauer is one of my favorite nonfiction writers. There’s nothing dry and boring here–it reads, as all of his books do, as briskly and vividly as a novel. Into the Wild is the true story of a privileged college grad, Christopher McCandless, who gives away all of his money, burns the rest, and hitchhikes to Alaska to live off the land. The book is heartbreaking and tragic (and it will make you appreciate the grocery store on your corner). There is romance here, the romance of wilderness and nature and possibility, but it’s also a sobering look at youthful idealism. –Emma S.

Girldrive: Criss-Crossing America, Redefining Feminism
Nona Willis Aronowitz and Emma Bee Bernstein
2009, Seal Press

In 2007, friends Nona Willis Aronowitz and Emma Bee Bernstein set off on a road trip across America to speak to young women about their relationship with feminism. The resulting book is both a diary of their trip and an archive of their findings, with brief portraits and interviews with more than a hundred different women. What’s especially fascinating to read about are all the different connections that girls had with the word feminism. Some enthusiastically claimed the title, others felt alienated by the feminist movement’s tendency to privilege certain voices, and to many, it was a completely foreign concept. Aronowitz and Bernstein’s travels felt honest, and I appreciated their attempt to expand the conversation beyond women who may already be entrenched in the discourse of social justice. –Anna

Wild: From Lost to Found on the Pacific Crest Trail
Cheryl Strayed
2012, Alfred A. Knopf

Cheryl Strayed is a badass. When she was in her 20s, she hiked the Pacific Crest Trail by herself. That’s 1,100 miles. All her toenails fell off, and she was divorced and mourning her mother, and she just kept going. This memoir details Strayed’s entire journey–including what happened prior to the hike that made her do it in the first place. It’s a searing, honest read–she doesn’t always come off well, and that seems to be the point, because the truth isn’t always flattering. With this book, as well as her Dear Sugar advice column for The Rumpus, Strayed has earned my trust forever. –Emma S.

It Chooses You
Miranda July
2011, McSweeney’s

This might sound blasphemous, but I was never a huge Miranda July fan before this year. I mean, I respected the hell out of her as a person and an artist, but I never felt a deep connection to her work–that is, until The Future found its way on Netflix (and subsequently into my heart). This book is an accompaniment to that movie. July, who is having trouble finishing her screenplay, answers classified ads in the PennySaver. She goes to the homes of various people in Los Angeles, interviewing them about the histories behind the objects they are selling. A few reviews that I’ve read of this book were critical of the way July would always relate her interview subjects to her own experiences and, subsequently, her difficulties in writing her script. I had the opposite reaction–I loved the insight into her artistic and creative process, and the significant influence of interacting with strangers. —Anna

Saving June
Hannah Harrington
2011, Harlequin Teen

This is a book about road trips, classic rock, friendship, love, family, and grief–that particular kind of grief for someone who committed suicide and left behind a million unanswered questions. Harper Scott’s sister, June, was one of those girls who seemed to have everything going for her, but two weeks before her high school graduation, she killed herself. After Harper’s divorced parents decide to split June’s ashes between them, Harper steals the urn, determined to take June to the place she always wanted to go: California. Her best friend Laney accompanies her, as does Jake, a guy June tutored in math. Jake made June mix CDs, including the one she was listening to before she died, and he also has a big secret. Saving June is one of those beautiful, character-driven books where the people are so relatable and real, they could be your friends (or you). For someone like me, who took a road trip to cope with grief, this story rang so true, but even if you haven’t been through anything like that, Saving June will break your heart and mend it at the same time. –Stephanie ♦