100 books like Tropic of Cancer

I’ll end with a book that started it all for me!

I still remember, in the year 2010, reaching the end of the essay "Goodbye to All That" where the date of publication is noted—1967—and how startled I was to realize something that feels so contemporary and alive had been written decades earlier. As in so much of her work, in this collection Didion offers vivid details from her life and brings her extraordinary powers of analysis to understanding their meaning.

As she once put it herself—in another essay, "Why I Write"—"Had I been blessed with even limited access to my own mind there would have been no reason to write. I write entirely to find out what I'm thinking, what I'm looking at, what I see and what it means.”

With its repetition and echoing of phrases, Kafkaesque chronology, and circular logic, Catch-22 illustrates the absurdity of war more than any other novel I have read.

Every time pilot Yossarian, the book’s anti-hero, gets close to flying the number of bombing missions required to go home, the requirement is raised. A paradoxical catch keeps them flying. If you ask to be grounded because you understand the dangers, you aren’t insane. Insane soldiers just need to ask to be grounded. But asking proves you aren’t crazy.

Beneath the absurdist comedy, there is an existential dread at the heart of the book. The death of Yossarian’s friend Snowden leads him to see that ‘Man was matter.’ For me, this is the dreadful secret that war exposes - the precarious preciousness of life - as our fragile bodies are turned to quiet, still matter.

Hunter S. Thompson’s books tend to have a lot of drug use in them. So do mine, although not at nearly the same scale. The way Thompson describes the drug use and deranged behavior associated with it is powerful and equal parts tragedy and comedy.

More than anything, Thompson’s cracking prose brings the debauchery to life and makes it relatable to anyone who ever may have gone one toke over the line. I used to give this book to friends who hadn’t cracked a book since high school and told them, “Just read the first page.” Every single one of them borrowed the book and read it cover to cover.

I stumbled onto this book at way too young of an age.

It’s vulgar, graphic, and crude—but one of the best expressions of Jewish anxiety and the sense of “otherness” I’ve read. It’s both funny and revealing. And with a return of sexual repression, male anxieties, and incel rage, this book is again relevant.

Oh man, this book! It’s everything I want: Sweet, simple, cute, nostalgic, at times, just awful. Gutterboys taught me that a book with a soul and a soundtrack and a firm jab in the gut is the type of book I want to make. Set in the 80s, Jeremy is a naïve suburban Jewish teen who falls crazy-stupid in love with a gorgeous older hustler. Colin won’t date Jeremy, but he does take him on a New York adventure that will only unhinge innocent Jeremy more and more. If you like that intoxicatingly toxic unrequited gay love, give it a go!

This is the Granddaddy of earthshattering, perspective-changing books: philosopher Michel Foucault’s nimble dissection of the rise and the role of sexuality in the Western world. Written, and surely meant to be read, more like a Homeric epic poem than an academic treatise, every single sentence in this book quivers with energy and perception. From pithy aphorisms like “The sodomite had been a temporary aberration; the homosexual was now a species”, to heady pronouncements such as ‘”Power relations are both intentional and nonsubjective”, this book is a gift that perpetually keeps on giving. Guaranteed to blow your mind.

Every generation believes that they see further and think deeper – and weirder – than every one that came before. From this perspective, we imagine that we can do everything differently that those who preceded us. In this book, one of the creators of the so-called New Journalism shows just how wrong we are. In particular, Talese provides a tour of the history of sexual mores, how cultures reflect those mores, and how tradition turns out to be a more powerful cultural magnet than we expect. We can try to make our own new ways in a lot of areas, but the biological pull we all experience invariably pulls us back to a few tendencies and trends we will likely never shake as a species.

A small number of Scots at the end of the Victorian era and throughout the Edwardian era were eager to live in a world ungoverned by Protestant Christianity and unrestricted by its strict sexual morality.

Cheadle introduces readers to socialists, freethinkers, and writers in Glasgow and Edinburgh who advocated for sexual freedoms grounded in new forms of political, religious, and cultural thought. One example is Jane Hume Clapperton, who was deeply involved in the suffrage movement, described birth control methods in her 1888 novel Margaret Dunmore, and demanded full sexual freedom for women. 

Sexual Progressives brings them to life, showing how they questioned dominant morality and envisioned a way of life in which people could prioritize sexual freedom and pleasure. You won’t forget them.

Helen Hamilton Gardener secured crucial support from leading politicians in Washington, DC for the 19th Amendment’s ratification. Despite her significance, few know the story of her exciting and controversial life. Fortunately, Kimberly Hamlin tells Gardener’s dramatic story in her book Free Thinker. Born Alice Chenoweth in 1853, she had to leave her job as a teacher in Ohio after an affair with a married school commissioner in 1876. She adopted the name Helen Hamilton Gardener and a range of modern ideas: women’s rights, opposition to the sexual double standard, and freethought. Gardener eventually became the highest-ranking female official in the federal government by the time of her death in 1925. Free Thinker provides a fascinating glimpse into the behind-the-scenes politics that led to the 19th Amendment’s ratification.

This book made me reflect deeply on whom we praise as trailblazing “rebels” and who we ignore, erase, or brand with criminal status in the stories we inherit and then repeat thoughtlessly.

Hartman reimagines “transgression” through the lenses of race, gender, sexuality, and class in early 20th-century New York and Philadelphia. She immerses us in up-close and poignant stories of women’s nonconformity, showing how their choices were flexes not only for survival but for thriving, a refusal to be defined by the ugliest social denigrations of their time (as well as our own).

Wayward Lives is richly sourced, including recovered photographs with the evocative literary portraits. It is a moving, haunting, unforgettable book.