10 Books That Remind Us of the Best and Worst Parts of High School

Logan Lerman, Emma Watson, Mae Whitman, Ezra Miller, and Erin Wilhelmi in The Perks of Being a Wallflower (2012)/Photo by John Bramley © 2011 Summit Entertainment

How do you remember high school? Do you look back with sepia-toned fondness, or with dread at the awkwardness that seemed to define your very existence? Truthfully, it’s probably somewhere in the middle. If I cut out the depression-inducing realization of “Wait, high school was how long ago?” it makes it a bit easier to look back on the time for what it was: a bizarre, exciting, messy, and occasionally spectacular transition from adolescence into adulthood.

Given that high school is a near universal experience, it’s not surprising that a myriad of books have been written about the experience. It’s also not surprising that, much like high school itself, they run the gamut from terrifying, to groan-inducingly awkward, and to bittersweet elation. So, as a reminder that high school was the best and worst of times, check out these ten novels.

  • The cover of the book Carrie


    Why not start with a literal worst case scenario, right? Stephen King’s debut novel is an exercise in teenage cruelty. Though the tragic tale of Carrie White is tinged with the supernatural and finishes with a horrifying climax, it’s the isolation of Carrie that provides a well-drawn view into the darker side of high school.

  • The cover of the book The Spectacular Now

    The Spectacular Now

    This is one of my favorite tales of teen romance because it feels surprisingly genuine and lived in. Sutter Keely is the outwardly boisterous life-of-the-party, determined to live in the moment. Aimee, on the other hand, is a quiet outcast – until Sutter enters her life. Though these two seem like walking stereotypes, thanks to Tharp’s razor sharp writing, they are anything but, and the bittersweet ache of their romance makes this one well worth a read.

  • The cover of the book The Perks of Being a Wallflower

    The Perks of Being a Wallflower

    It can be easy to forget the trepidation that came with entering high school for the first time – the jumble of nerves, misgivings, and anxieties. It’s a feeling that Stephen Chbosky perfectly captures in The Perks of Being a Wallflower. The novel is also a brilliant reminder of the wild highs and lows that so often define the high school experience.

  • The cover of the book Nick & Norah's Infinite Playlist

    Nick & Norah's Infinite Playlist

    Thanks to the storm of adolescent hormones, romance is a keenly felt part of the high school experience. Whether it’s the ache of a first real crush, or the devastation of a first broken heart, it was all heightened. Nick and Norah’s Infinite Playlist nails not only those feelings, but also that particular sense of teenage freedom and adventure.

  • The cover of the book Simon vs. the Homo Sapiens Agenda

    Simon vs. the Homo Sapiens Agenda

    Equal parts hilarious and heartbreaking, Simon vs. the Homo Sapiens Agenda explores the complexities of high school relationships and identity through the eyes of a remarkably witty and incisive teen named Simon. Simon is sixteen – and not-so-openly gay – when he makes the mistake of leaving his email account open on a public computer. He’s forced to confront not only the casual cruelness of his classmates, but also his own identity and just what coming out might mean.

  • The cover of the book Eleanor & Park

    Eleanor & Park

    Remember the first time you fell in love? Really head-over-heels, seemingly life-altering in love? If not, Eleanor & Park might just be the perfect reminder. Adolescent romance is a tidal wave of emotions and complexities – it’s urgent, all-encompassing, exquisitely painful, and enthralling. Rainbow Rowell’s tale of two star-crossed misfits gets it absolutely right.

  • The cover of the book Looking for Alaska

    Looking for Alaska

    With all due respect to The Fault in Our Stars, John Green’s first novel may still be his best. Pudge Halter’s yearning for adventure and “the Great Perhaps” represents John Green at his most identifiable, and Alaska Young manifests everything the author does so well – she’s beguiling, infuriating, and most of all, real. If you still don’t know what all the John Green fuss is about, this is the place to start.

  • The cover of the book The Absolutely True Diary of a Part-Time Indian

    The Absolutely True Diary of a Part-Time Indian

    It’s likely that we all had moments of feeling like an outcast in high school – there’s a reason that it’s such a pervasive theme in coming-of-age novels, after all. Few pull the coming-of-age-misfit off quite as well as Sherman Alexie does with Arnold Spirit, Jr. in The Absolutely True Diary of a Part-Time Indian. It’s a brilliantly funny and self-aware view into the life of a kid trying to find a new life beyond the one he knows.

  • The cover of the book The Most Dangerous Place on Earth

    The Most Dangerous Place on Earth

    A Novel

    Unfortunately, the experiences of our teen years are filtered through a prism of casual malice that is sometimes unfathomable to our adult selves. It’s an often all-too-real part of the high school experience. The kaleidoscopic narrative of The Most Dangerous Place on Earth displays all of these complexities, complications, and cruelties front and center.

  • The cover of the book Election


    Remember all the high school cliques? Or that one seriously over-achieving kid who seemed to be involved in literally everything? What about that one teacher who seemed way too involved in student goings-on? Clearly, Tom Perrotta does. While Election fiendishly skews toward the satirical, it’s nonetheless a great reminder of just how cut-throat school politics could be.