97 Books Like Rolling Nowhere

This book hit me as both tragic and strangely hopeful.

Chris McCandless walked into the Alaskan wilderness with little more than a backpack and a stubborn streak, and people have argued ever since: was he brave, reckless, or just plain stupid? But his compulsion isn’t as rare as we might think. In my book, Cole feels the same tug—escape the sterile shoebox apartment and the $8 lattes. This can’t be all there is.

What drew me in wasn’t the verdict but his hunger for something real—stripping away every layer of artifice most of us cling to. Krakauer tells it with empathy and curiosity, letting you wrestle with the questions instead of handing you neatly typed answers. I recommend it because it forces you to stare down your own compromises: freedom versus responsibility, idealism versus pragmatism.

Admire Chris or dismiss him, you won’t forget him. And the story lingers like a… show more.

This is classic literature in the realm of American travel.

I had no idea that “blue highways” existed, and even though Heat-Moon went cross-country back in the 1970s in his van equipped with his igloo cooler and makeshift bed (not like the $100k fancy campers you find today), the type of people you meet and experiences you have in this amazing country are still relevant today.

In Blue Highways Revisited, I was shocked to read how long it took for this book to get published and the stacks of printed-out drafts he had of it (I think it was like four feet high). If there are any travel writing classes taught as part of a creative writing program, then Blue Highways better be on the list. 

Well-known American author Jack London experienced a genuine decline into vagrancy in the US during the late nineteenth century.

In his 1907 memoir, he depicts the realities of the vagrant’s life without flinching. The detailed descriptions of begging for sustenance from strangers’ homes, risking death to evade detection on fright trains, and the life of inmates in the state penitentiary are as gripping as they are appalling.

The only US book in this collection of recommendations, The Road confirms very similar experiences and challenges facing the homeless on both sides of the Atlantic.

I, Ruchin, like Zen and the Art of Motorcycle Maintenance for multiple reasons.

It is a father-son story, yet it includes how their family and friends shape their experiences. I like it because the motorcycle itself transforms into a human-like character, adding depth to the dialogue.

I also like the storytelling style; it is vivid. You can see each scene unfolding before you. And lastly, I appreciate how it draws on the Hindu and Buddhist values I grew up with, making the book even more relatable.

At the same time, I find the book a little dated in its voice and perhaps too long for readers today.

The go-to book about voluntary homelessness, I always appreciate George Orwell’s amazing writing. It’s hard to put down.

The first half is about his time as a lowly kitchen assistant in the basement of a Parisian restaurant in the 1930s. The brutal divide between the rich and the destitute is better depicted here than in anything else I’ve ever read. The second half describes his time back in England and provides a heart-rending understanding of why homeless people are referred to as tramps and the ultimate emptiness of church-organized aid.

Although Orwell always had the option to opt out, his study of the lived experience of homelessness and the skill with which he captured it afterwards stand out as a colossus of the genre.

From the very beginning of her writing career, I’ve loved the novels of P.D. James. Her clear-eyed understanding of the human condition, and the precision of her writing, have always set her a bit apart from other writers in the genre, but this novel blew me away. As she explores the death of two men in the crypt of a London church—one a prominent member of Parliament, the other a homeless vagrant—she transcends genre altogether and creates a work of such depth and complexity that it resonates with me still, many years later. She wrote some fine books both before and after, but this will always be for me the high water mark of one of my all-time favourite writers—and role models.

Imagine it’s 1958 and you live in Paris. Imagine your father dies and you lose your home and your mother has to work. Imagine you spend a day in the company of a grumpy old man walking all through the city. Imagine kindness and friendship doing their magic to keep everyone safe. Yes, The Family Under the Bridge is an old-fashioned book with a few shortcomings, but we recommend it nonetheless. This story celebrates Paris and all the generous and delightful people roaming its streets.

This work is not a history book but a collection of Zora Neal Hurston’s writings. Hurston wrote fiction and nonfiction and was a trained anthropologist. Her work taught me that history is oft-times found in the strangest places. This reader did this for me – a writer and anthropologist Hurston was. When I read the reader, I wanted to raise my hand and ask questions. Other times, I remained silent, only talking to myself and thinking.

In my former life as a trial lawyer, I remember quoting her writings in a final argument to explain language and culture. As my voice broke, tears flowed – this was the first time I explained the power of this book. They understood, and some of my jurors cried with me.  

The reader gets a three-for-one deal in this incredibly thoughtful book: an intimate look at two towering anthropologists by their daughter, a distinguished anthropologist herself. Mary Catherine Bateson understood her difficult parents and their groundbreaking work as well as anyone could.

Talking to her father, she wrote, was “a form of argument that was also a dance.” Her mother was “a one-person conference.” The reader gets to know each member of this remarkable family through insightful anecdotes, rare family photos, conceptual diagrams, and lucid prose.

A wonderful introduction to, or return visit with, a strikingly interesting and groundbreaking legal anthropologist. Moore's writing is clear and confident, and her thinking fascinating. This book is, to my mind, an invitation to undertake again, at any time, the joys of being a student. Why? She models so well the curiosity, care, and rethinking that are the essence of being a student.