The best books ever from the unheard voice of homelessness

With a title good enough to inspire the naming of a famous British band, Welsh poet Davies’ 1908 love letter to tramps and hobos drew directly from his own experience as a drifter in the US in the late nineteenth century.

Davies captures the life of jumping freight trains, joining the gold rush, and paying “boodle” to stay in the relative comfort of American jails. I love this book because it depicts the romanticism of the wandering mendicant without painting over the cracks of the hardships of roofless life (including parting company with one of his legs under a train).

There also are moments of humor (e.g., learning how to sleep standing up!) and the fascinating account of struggling to get his writing published on his return from his travels. It’s a classic.

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.

The only work of fiction on the list, Nobel Laureate Kurt Hamson’s Hunger (1980) was a game changer for modern literature.

Firmly anchored in the point of view of the narrator, we journey painfully with a man, a writer as a matter of fact, on the way down into the depths of meaningless, despair, and hunger. Adapted into several films, the story reflects how little society values the intellectual capital of people it perceives as the dregs and describes in detail the effects of starvation on the human mind.

A worrying and unsettling read, Hunger remains the best work of fiction ever written about destitution.

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.

John Healey’s stinging 1988 memoir of 15 years as an alcoholic tramp in London remains the most shocking of all descriptions of the sheer brutality of life on the cold streets of the capital.

A former boxer, Healey was no stranger to violence, but the detached way in which he describes it amongst homeless men (and women) adds a chilling edge to what we don’t see when we walk past a beggar. It was prison that saved Healey – while incarcerated, he carried on writing and discovered he had a talent for chess. But the horror of the dog-eat-dog life of homeless people in the UK will haunt me for a good while to come.