1. Zen and the Art of Motorcycle Maintenance by Robert Pirsig
A professor relates his struggles with mental illness, with his philosophy, and with what it means to have a good life, all through the course of a motorcycle trip across of the United States. It’s truly life-changing.
2. The Kite Runner by Khaleed Hosseini
A man struggles to find forgiveness and love amidst a war torn Afghanistan and his subsequent immigration to America. A work stuffed with florid prose and subtle depictions of small beauties throughout.
3. The Great Santini by Pat Conroy
The story of growing up as the oldest son of an alcoholic, abusive, Air Force father, and how much you will always love him, regardless.
4. A Confederacy of Dunces by John Kennedy Toole
Sometimes called a “fart joke as literature,” this book is my personal favorite. It’s the tale of Ignatius P. Reilly, the walking embodiment of why the pursuit of knowledge is useless. It might come off as gibberish, or it might make you question why you read books at all.
5. Stone Butch Blues by Leslie Feinburg
A book about a lesbian who begins to pass as a man and the struggles that come with being transgender in America. This one tells the struggle of equality for all, and ties into the labor movement.
6. The Ultimate HitchHiker’s Guide to the Galaxy by Douglas Adams
Couple drab British humor, science-fiction, and thoughts on the nature of time and space and you get this unique work. Remember, the answer is 42.
7. A Heartbreaking Work of Staggering Genius by David Eggers
What would like to be nineteen, barely legally an adult and have custody of a six-year-old? Eggers nails the confusion of that tenuous age in this work.
8. Everything Is Illuminated by Johnathan Safran Foer
A book about finding your roots, travelling to the country your people are from, and the nature of cultural memory played out over several decades. And a dog named Sammy Davis, Jr., Jr. This is a brilliant work.
9. One Flew Over the Cuckoo’s Nest by Ken Kesey
Set in an mental institution in the 1940’s or so, this book follows Randall Patrick McMurphy and hints at how mental illness is all relative, and how, sometimes, men never quite grow up.
10. The Brief, Wondrous Life of Oscar Wao by Junot Diaz
A truly entertaining read, the story of a fat, lonely Dominican boy in New Jersey, the story of his beautiful mother in the Dominican Republic, and the story of loss, love, family, teenage romance, going to college, and living under a brutal dictatorship all in one.
11. Immortality by Milan Kundera
Translated from the original Czech, this book is a beautiful account on the nature of aging, and the ways that a person can be many ages at once.
12. 100 Years of Solitude by Gabriel Garcia Marquez
Marquez uses mysticism to speak to the nature of time and family heritage in his work about one family in the fictional town of Maconda, Columbia. Just try to keep track of the number of the Jose Arcadio Buendias over the course of seven generations.
13. A Clockwork Orange by Anthony Burgess
Written in futuristic British/Cockney slang that is so dense it has its own Wikipedia translation page, this one is a challenging read. But once you get the hang of it, the question of whether it’s better to be good by choice or by force is brought to the fore.
15. American Psycho by Bret Easton Ellis
You may have heard of the movie, but the book is a tour-de-force, expounding on the nature of the 1980’s, a time when corporate businessmen where literally allowed to do anything they want. It makes you question the interchangeability of people and the nature of mental health.
Now, if you’ll excuse me, I have to go return some videotapes.
16. Invisible Monsters by Chuck Palahniuk
From the author of Fight Club, Invisible Monsters is about Brandy Alexander, a striking beauty, and is told from the perspective of someone unable to communicate because they missing their lower jaw. It’s gut-wrenching and nasty and twisted in all the right ways and will make you appreciate the grace of ugliness.
16. Slaughter-House Five by Kurt Vonnegut
A science fiction-infused recount of the massacre that was the Allied bombing of Dresden during World War II, this book will make you question the nature of experience and the limits of time and space.
17. The Things They Carried by Tim O’Brien
A book about the stories that may or may not have happened during the narrator’s experiences during Vietnam. This one hints at the nature of storytelling itself, and why exaggeration may be the only way to get your point across.
18. The Curious Incident of the Dog in the Nighttime by Mark Haddon
Told from the perspective of an autistic boy, this book hits perfectly on what it is like to have a family member with special needs. The author spent a lot of time working professional with special needs patients, and no other book approaches illustrating social disorders this way.
19. The Jungle By Upton Sinclair
Set in the meat-packing industry in Chicago in the 1900’s, this book illustrates the story of Jurgus Rudkus, a Lithuanian immigrant who toils day and night. After losing everything, he finds solace in local politics and eventually embraces socialism.
20. Americanah by Chimamanda Ngoze Adichie
This one follows the loves and struggles of a young Nigerian woman as see moves to America to attend school. While we think of America as the perfect end destination for many cultures, this one will make you question the struggle to fit in that many immigrants experience.
21. Midnight’s Children by Salman Rushdie
A book that incorporates magical realism into a story surrounding the independence of India from British rule, this one will amaze you with prose and stretch your thoughts about destiny.
22. Infinite Jest by David Foster Wallace
Coming in at a staggering 1104 pages, Infinite Jest is a modern day Moby Dick that will make you question the nature of sanity, of the coming future, and addiction and recovery.
23. The Alchemist by Paolo Coehlo
Set as a boy makes a pilgrimage from Spain across the desert of North Africa in pursuit of his destiny, Coehlo weaves a story that will change how you look on fate, love, and finding your place in the world.
24. On the Road by Jack Kerouac
A whimsical novel about the Beat generation, this one will show you what the pathos of the 1960’s was all about, and give you insight into a movement that shaped America and the world at large.
25. Trainspotting by Irvine Welsh
Ever wondered what it’s like to be addicted to heroin, to addiction, and to anarchy as a whole? This book will show you what it’s like to have been a punk rock kid, have grown up, and have the same need for thrills regardless of age.
Featured photo credit: Geir Halvorsen via flickr.com
