100 Books Like The Outsiders

A deserved, all-time classic, this book seems to transcend time to capture the spirit of wanderlust. I was young and impressionable when I read it for the first time, and it inspired a sense of profound restlessness to explore, grow, and hit the road to see for myself. 

Neal Cassidy and Jack Kerouac are wild, occasionally unhinged protagonists, and their journey consists of hustling, romance, and drinking their way to a good time. Kerouac’s writing made me long for similar misadventures, where life is simple and finding the road is all that matters. Subversively, the novel promotes a full life and whole human experience, which makes working 9 to 5 that much more difficult.

I would have thought to list another book here, and for sure, there are truly many books to be read that could easily be listed here, and despite that, this is listing Tolkien’s works for a third time; the truth simply stands in my library that his works are simply that great. 

So far be it that the renowned book of The Lord of the Rings be not included. I had been introduced to Tolkien and fantasy’s more serious nature by my dad and grandfather with readings of The Hobbit, and by it, I was already enamored with the world of Middle-earth, as Bilbo was my hero.

I loved the classic animated cartoon adaptations back then by Rankin and Bass, and Bakshi, which at the time was my main exposure to The Lord of the Rings, along with commentaries from my dad, until I finally read it at the time… show more.

What I love about this book is how it shows that rural schools offer communities more than just a classroom education.

In this case—for better and for worse—it’s sports. And Bissinger wades into it all: tensions between education and sports, the economic unraveling of Texas oil country, the costs of racism, and the pure adrenaline of a Friday night football game.

Not every rural community is as sports-addicted as Odessa, but all have their imperfections and fault lines—so much about this book resonates.

This is a dark, scary story about a world ruled by fear.

Orwell is the father of the dystopian novel, in my opinion. I loved this book not only because Orwell created a great atmospheric novel, but his words create vivid pictures of such a society – better than the film.

I’m a sucker for a Southern gothic page-turner, particularly one that features such a complicated character like Joe Ransom who, when you first meet him, you don’t know if you should approach or just run away. Then bring teenage Gary into the mix with his troubled family backstory and this sheds a new light on Joe, and Gary as well, as the two traverse the muddy path to redemption.

Brown’s descriptive prose paints a harsh picture of the world, warts and all, yet it also has an underlying tragic beauty. 

I was wrung out after finishing this book and immediately looked around for someone else who’d read it. I needed a shoulder to cry on. If Endless Love is about lives undone by teenagers driven insane by love and lust, then this book is its counterpoint: two teenage outsiders whose love and understanding help them survive.

There’s awfulness in Eleanor’s life, but there’s also exchanging comics and listening to Joy Division with Park on a shared walkman on the school bus. I loved these characters completely and rooted for them with everything I had. 

This made me laugh, and it made me cry. I challenge anybody with a heart not to feel for Augie Pullman as he not only survives a new school and new situation but thrives in them. He doesn’t just overcome his self-doubt; he proves to himself and everyone else that he’s not only his classmates’ equal but their superior. Augie surpasses every single other child character in this book with his compassion and intelligence. He is a hero of the 21st century. 

As cliché as it sounds, I couldn’t put it down. In between reading sessions (that I undertook with my daughter), I found myself obsessing about Augie’s plight and wondering what would happen to him next. I needed to know how the young boy with the messed-up face would respond and react to whatever challenges the world, his school, his town, his family, and his friend threw at him.… show more.

Kaya Clark is the wild child I longed to be growing up. Although her family story is tragic and well-explored, how she inhabits her world of nature and allows it to inhabit her is stunning. Once again, she is a young woman who is an outcast who manages to rise above her limitations and those placed on her by society. 

Beyond the incredible storytelling and intriguing plot lines, I was mesmerized by the natural world of the North Carolina marshes, being as much a main character as Kaya herself. The intricate details of the lushness and cruelty of the natural world were incredible. In looking back at my favorite novels, one of the commonalities is the writing’s ability to come alive in my head and to take up a permanent space as much as my own lived memories. This novel is one of those.

Set within the greatest mass migration in American history, Steinbeck’s 1939 classic follows the Joad family as they join nearly three million others who escape the Dust Bowl of the American Midwest.

Usurious banks have foreclosed and crushed the bereft farmers. More than 200,000 refugees head for California, and the Joads join them in an ambling caravan of rattling jalopies. Young Rose of Sharon moves pregnant across the continent, emblematic of both the promise and the peril of the human condition. She’s surrounded by family and hangers-on who ford the wasted continent, only to face a glut of labor in the vast farms of California and the brutal exploitation of the owner classes. The Joads are slapped with the bitter understanding that the promise of California exists largely in myth. Yet always Steinbeck returns to the promises of human connection and even happiness that beckon from just over the next… show more.

If you want a break from fantasy and sci-fi, and you love a book with morally grey characters, then this is it.

Beartown is a town that survives on hockey. The kids play it, the grown-ups work in anything related, and just like in sports, both sides consider themselves the good side in every action they take.

We follow the manager of the hockey club as he must make impossible decisions, then the players, each making their own mistakes. We see villains grow from a place that we can understand, and we see good people making bad calls because no one can be perfect all the time.

And most importantly, we see how sometimes, no choice is the right choice. Especially for the victim.