1. Rabbit, Run by John Updike
The Gist: Harry “Rabbit” Angstrom, a onetime high school basketball star and full-time man-child, impulsively abandons his wife and son.
The Takeaway: It’s a masterpiece of male, middle-class ennui and a behind-the-scenes look at the type of guy for whom the the grass is always greener on the other side..
2. On the Road by Jack Kerouac
The Gist: This Beat classic is a road trip novel about two young men traveling across the United States searching for experience and enlightenment.
The Takeaway: This book helped define American counterculture and cultivate our admiration for free spirits.
The Gist: Three brothers and their father try to make a life for themselves in the Montana wilderness. All the sons go to Europe to fight World War II, but only two return. A love triangle ensues.
The Takeaway: Harrison is the king of the rustic, laconic masculinity that Americans love. These are the kind of men that make regular men feel bad about themselves.
4. American Pastoral by Philip Roth
The Gist: Swede Levov is a Jewish-American man who has everything he could ever want: money, well-defined biceps, non-ethnic looking features, and a pretty wife. Then his radical hippie daughter starts blowing up things.
The Takeaway: This book sheds some light on the inner mechanics of the trophy wife phenomenon, including why men want them and what happens when they get them.
5. For Whom the Bell Tolls by Ernest Hemingway
The Gist: The story of Robert Jordan, a young American who goes to fight the fascists during the Spanish Civil War. There is a lot of violence and a beautiful girl named Maria with whom Robert falls in love.
The Takeaway: A great representation of the way femininity is mythologized during war. Women represent all that is fragile, beautiful, and innocent. Eden before the fall.
6. Tropic of Cancer by Henry Miller
The Gist: Originally banned in the United States for obscenity, this is a largely autobiographical, non-linear novel about Miller’s time in bohemian Paris in the ’20s and ’30s.
The Takeaway: The female characters might lack depth, but the presentation of sex as vice, even addiction, does not.
7. The Adventures of Augie March by Saul Bellow
The Gist: Bellows tell us the story of Augie March, a fast-talking, free-spirit who leaves his family of poor Jewish immigrants to search for success, meaning, and love.
The Takeaway: Augie may lack respect for women (beginning with the disdain he feels for his mother), but his reverence for life is something to which everyone can relate.
8. Women by Charles Bukowski
The Gist: Henry Chinaski is a poet who has just earned enough fame to leave behind his previously hardscrabble life. There’s a rotating cast of of women, none of whom can satisfy this man on the rise.
The Takeaway: He’s a pathological womanizer. Allow him to explain himself.
9. Lolita by Vladimir Nabokov
The Gist: A European expat named Humbert Humbert has an unhealthy obsession with a girl he calls Lolita. Lo. Lee. Ta. He kidnaps her and takes her on a road trip around cheery postwar America.
The Takeaway: This is a meditation on love and eros that is both disturbing and hypnotizing, written by one of the greatest prose stylists in history.
10. The Adventures of Huckleberry Finn by Mark Twain
The Gist: Huckleberry Finn is a young boy who runs away from home and sets off down the Mississippi River where he meets a runaway slave named Jim. The two have a series of escapades during which Finn is confronted with the reality of racism.
The Takeway: The women in this book are mostly nags, shrews, or dummies who stay in the periphery. Nevertheless, the book’s portrayal of racism, as well as the very American sense of momentum it conveys, makes for a very worthwhile read.