74 Books Like Rough Sleepers

This whole book is a powerful exploration of alcoholism, homelessness, and the father-son relationship, but it was a single chapter that made me write “WOW” in the margins.

“Same Again” is a four-page chapter composed of nothing but short sentences that contain only euphemisms for alcohol, from “the usual” to “same again.” That sounds like it wouldn’t work, but it does. It’s poetic, gripping, and follows a narrative arc through a single evening at the bar.

Read the whole book, but don’t skip this mesmerizing chapter.  

I met the poet Nick Flynn over twenty years ago, not long before the publication of his most famous book, Another Bullshit Night in Suck City, a memoir about his father’s homelessness. Since then, he has become one of my favorite writers. The Reenactments—for my money, his best book—takes us through the surreal experience of Another Bullshit Night being turned into a film. Robert De Niro plays his father and Julianne Moore plays his mother. De Niro meets Flynn’s father, studying him for character traits. In the most heartbreaking sections, Flynn relives his mother’s suicide as it’s filmed. As Flynn writes: “How often are you offered the chance for a complete reenactment of the day of the disaster?”

Here’s another PI series set in Boston, and while Carlotta Carlyle is nowhere near as well-known as Spenser, Linda Barnes is every bit as readable as Robert Parker. In her first outing (an Edgar Award nominee for Best Novel), ex-cabbie and ex-cop Carlyle takes on a missing person case that has her tangling with IRA gunrunners. A Trouble of Fools is my pick because it brings the ‘80s Boston I remember to life, and because of the light, humorous voice Barnes lends the proceedings.

Detectives Sarah Kelling and her much-loved husband Max Bittersohn live in her inherited house on Beacon Hill, Boston. These are detective novels of the cozy and charming sort, and because of the relationship between Sarah and Max are adventure romances as well.

Sarah has a large extended family and they enter into all the books as friends. This makes each one a friend and fun to read. MacCleod knows Boston and her descriptions of the habits and haunts of classic Beacon Brahmins/Yankees are as charming and rich as her plots. I recommend this and her other books for the fun of reading and the great plots.

This is a complex young adult contemporary novel that spotlights Mini as she singlehandedly organizes the wedding-of-the-year for her older sister and her fiancé. Amidst the primary plot of Mini pulling together the wedding and falling in love with the handsome Vir Mirchandani, there is a unifying theme of family. Nandini Bajpai does an incredible job of unpacking the elements of an Indian family, specifically in how they support each other after the loss of a loved one. It was heartwarming to see Mini come into her own by the end of her story, and I highly recommend this book to anyone with a penchant for Indian weddings, Indian culture, and young love. 

Everyone knows that the Puritans settled in Boston and the Quakers settled in Philadelphia. What I found surprising is Baltzell’s argument that the two cities’ founding religions shaped their respective character for hundreds of years afterward. And, he says, the difference between Puritanism and Quakerism explains why Boston and Philadelphia played such different roles in American history.

As great as it was, Eddie Coyle didn’t leave much of a cultural footprint, at least not until the movie adaptation starring Robert Mitchum was rediscovered decades after its initial release. Robert B. Parker’s Spenser is another matter entirely, having spawned nearly 40 novels by Parker, another 10 by Ace Atkins, a popular ‘80s TV series, and a Netflix movie starring Mark Walhberg. Picking just one of the durable shamus’s adventures is a daunting task, but I’ll give the nod to Ceremony for its evocation of the seedy seventies Combat Zone (Boston’s long-gone red light district) and the murky morality of Spenser’s dealings with a teen runaway turned sex worker.

Robert B. Parker’s Cold Service is one of my favorite Spenser novels because it provides more insight into the character Hawk. Hawk is in the hospital, three bullets in his back from trying to protect a bookie from the Ukrainian mob. The Ukrainians are spreading their turf from NYC to the Boston area (a town called Marshport). Spenser comes to the rescue, and the two men take on the impossible task of defeating the Ukrainian mob and their Afghani heroine-dealing overlords while avenging Hawks shooting. Alone, Hawk can’t deal with the thought of showing weakness and Spencer ponders his mortality. Together Spenser and Hawk appear to be invincible. Their code allows them to engage in brutality and come out as likable characters. The way in which Parker spins a tale using simple dialogue is ingenious. His main characters Spenser, Hawk, and Susan Silverman are a joy to get to know… show more.

Civil lawsuits often get second-billing to criminal cases, but this book about a case of mass environmental contamination in a small town in Massachusetts one has all the traits of a legal thriller: an astonishing injustice, stunning twists and turns, and enormous consequences for all involved.

More than once, I gasped while reading this, and it’s one of the few books I ever re-read. This has since become a major-release movie (starring John Travolta), but the book is even better.

One of the most kinetic books I read a few years back and told in a kind of beautiful, white-hot stream of consciousness, Sketchtasy is the tale of young, genderqueer Alexa and her friends navigating pleasure and survival in mid-90s, AIDS-battered Boston.

This is no “model LGBTQ person” book; Alexa and her friends, scarred by trauma and addled by every recreational drug on the planet, are creatures of the night, showing off outrageous looks in the clubs and turning tricks to pay the rent and put food in their mouths.

It’s a breakneck-paced look at both exuberant and terrified young queer people right before HIV went from being a near death sentence to a chronic manageable disease.