100 Books Like An Irreverent Escapade

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.

A savage, icepick of a hitman novel that will bury itself in your cerebellum. It’s a slippery, sexy book about the making and subsequent unmaking of a contract killer, complete with all the usual trappings and a few resolutely unusual ones. halfway through this novel, I realized that there weren't any rules to this. That you just built humans from scratch and turned them loose in your world and whatever they did, they did.  A guy stabs someone with his own fibula in this book. Eat that Macgyver. 

Senseless is the embellished account of Nick Prince, a jaded census worker, who is required to prowl rural backwoods in search of the folks who, for one reason or another, didn’t return their completed census questionnaires as required by law. Bannon, who actually worked for over a decade in this role, explains that Title 13 of the U.S. Code forbids census employees from revealing anything they learn about the individuals they visit, under penalty of hefty fines and prison time. This conceit makes for some hysterical maneuverings that, according to Bannon, are based on some actual events he’s forbidden to relate in non-fiction prose. It’s hard to tell where fiction and non-fiction diverge as Nick encounters a sequestered polygamist compound far off the grid. Hilarity ensues when a desperate wife decides he’s her ticket out of captivity and she convinces him to help her rescue the rest of the clan… show more.

This book jumped out at me at a bookstore one day, and I loved it so deeply that I sought out the author when I learned he lived nearly and we became good friends.

Rubinstein stumbled upon a true crime story most reporters only dream of – that of hard-drinking third-string Hungarian hockey goalie Attila Ambrus, who took up bank robbing and triggered the largest manhunt in post-communist Eastern European history – and then was smart enough to let the story tell itself, bit by incredible bit.

The result is a wild ride through the chaos of post-Cold War Hungary with a rambunctious antihero for whom you can’t help but root.

Joseph Mitchell was the city reporter for the New Yorker for about half a century. This is a collection of his magazine stories. Many of them involve the old Fulton Fish Market, but he also wrote about weird things like dime museums, gypsies, and stag banquets. 

To me, every story in this collection is like a time capsule. This is the book that made me want to write about New York City because it suggests there is a history on every block there worth recording. If you don’t like a chapter or two, then skip to the next one, but I’ll vouch for 80% of this book being the best non-fiction writing that I have ever read (and I practically read for a living).

Published the same year as John Steinbeck’s The Grapes of Wrath, di Donato’s Christ in Concrete is another closely drawn portrait of working-class immigrants, this time the Italian-American bricklayers of New York City’s Lower East Side.

On top of its lyricism and spirited narrative pace, what I find most refreshing about di Donato’s tale is its choice of subject matter. So much of what we read and hear about the Italian-American experience tends to focus on the Mafia, perpetuating negative stereotypes that have dogged paisans since the late 19th century.

While I’ll never be the one to turn off Goodfellas, I long for more stories like that of Geremio and his irrepressible son, Paul, “born artists of brick and mortar.”

This book relates the story of Legs Diamond, who began as a street urchin working for Arnold Rothstein and then became a major figure among gangsters. Kennedy treats Legs as a mythic figure, larger than life, who was in the 1930s as much of the story as the Great Depression. The narrator, Gorman Marcus, functions as a kind of Nick Carraway, telling the story from an observer point of view. I admire Kennedy's ability to make Legs a likable figure, notwithstanding the corruption and the murderous instincts of the man. If readers want an intelligent gangster story, this is the book for them.

Constance Baker Motley’s role within the Civil Rights Movement had not received the recognition it deserved until Tomiko Brown-Nagin’s Civil Rights Queen. Brown-Nagin reconstructs Motley’s life and pushes readers to consider the activist and legal career of the first Black woman appointed as a federal judge. As a writer who is especially interested in studying Black working-class women, I appreciate the author’s close attention to how Motley’s life from a working-class background to her position as a judge of the Southern District of New York.

This one had my head spinning right round, baby! Happy marriage, babies, a nice home—what more could a young wife ask for?

How about someone she can trust, for starters, and how ’bout her husband’s ex-lover quits coming around all the time, tattling tales of his murky past? It reminded me of an old friend of mine who fell in love with a guy she’d met through an online dating site. He claimed he was long divorced, but—whoops—was actually still married, and living with his estranged wife in separate parts of their house.

You can probably guess how that ended, but not this book. With every wild plot turn, I was grabbing for the Oh sh*t handle and gasping for breath.

The utopian dreams of the 60s died hard, and this beautiful novel captures the mood of the decade—and the forces that destroyed it. Set mostly in a back-to-the-land hippie community, the book centers on Bit, the first baby born to the settlers. It follows him through childhood and adolescence, and checks in on him on the cusp of middle age, a single father in New York City. Bit’s a sensitive soul, and I felt for him, especially when the story tracked his relationship with his first lover and later runaway wife, the self-destructive Helle. Groff’s expressive use of language, her feel for the natural world, and her deep sensitivity to the psychology of her characters marks this book as a classic not to be missed.