1. The Virgin Suicides by Jeffrey Eugenides (1993) The haunting tale of the five Lisbon sisters' suicides, which was turned into a Sofia Coppola film starring Kirsten Dunst in 1999. 2. Generation X by Douglas Coupland (1991) amazon.com This is the book that solidified the term "Generation X" — it's an extremely postmodern novel about disaffected, ironic twentysomethings living in Southern California. 3. The Perks of Being a Wallflower by Stephen Chbosky (1999) en.wikipedia.org Although Chbosky's iconic coming-of-age novel was published just before the end of the decade, it takes place in the early '90s. Mixtapes are extremely central to the plot. 4. Ghost World by Daniel Clowes (1997) en.wikipedia.org Clowes's super-culty graphic novel follows the adventures of Enid and Rebecca, two cynical BFFs who just graduated high school. 5. She's Come Undone by Wally Lamb (1992) amazon.com The story of Dolores Price, a young, troubled, overweight woman, who observes life as an outsider and deals with her depression and childhood. 6. Bridget Jones's Diary by Helen Fielding (1996) thestir.cafemom.com A diary-style novel based loosely on Jane Austen's Pride and Prejudice , this funny read is an adventure inside the mind of a young, neurotic woman (basically, you) and a picture of the always-confusing dating landscape. 7. High Fidelity by Nick Hornby (1995) pinterest.com The tale of the record store junkie's breakup. Emo, music-loving boys are always a compelling read. 8. Naked by David Sedaris (1997) en.wikipedia.org Short stories from everyone's favorite comedic writer. The 17 essays take you through hilarious moments of Sedaris's youth as he contemplates the weirdness of life in North Carolina, and his dealings with homosexuality. 9. Prozac Nation by Elizabeth Wurtzel (1994) en.wikipedia.org Elizabeth Wurtzel's autobiography may have been highly personal, but it spoke to a larger cultural phenomenon of the '90s — a budding generation of extremely dark and sad teenage girls who struggled to find ways to treat depression. 10. Model Behavior by Jay McInerney (1998) jaymcinerney.com Although we tend to think of McInerney as a novelist of the '80s, this 1998 novel moves McInerny's familiar world a few years ahead—into the scene-y downtown Manhattan culture of the '90s. 11. White Oleander by Janet Fitch (1999) fanpop.com An introspective tale of a teenager who is transferred from foster home from foster home, and the extreme differences she experiences with a string of Los Angeles families. 12. Fight Club by Chuck Palahniuk (1996) fanpop.com A depressed insomniac helps start a Fight Club, a secret society where people beat the crap out of each other. 13. Dangerous Angels by Francesca Lia Block (1998) This anthology compiles all of the Weetzie Bat books, a young adult series characterized by dreamy prose, whimsical characters, and a backdrop of a dark yet beautiful Los Angeles. 14. Sex by Madonna (1992) cizgidiyari.com While this work put out by Madonna is more of an object — a coffee table book — it caused a stir (as if that's ever a surprise with Madonna) with its bondage photography and musings on sex. 15. Girl, Interrupted by Susanna Kaysen (1993) amazon.com A memoir of mental illness and Kaysen's time in a mental hospital, and the stories of her fellow female patients. 16. Glamorama by Bret Easton Ellis (1998) en.wikipedia.org This book is really fucking weird, but manages to make a satirical tap into the darkness and superficiality of the glitterati, as seen through the eyes of a beautiful male model. 17. Infinite Jest by David Foster Wallace (1996) phawker.com I mean. You know this one. The one you have pretended you have read. But really it is just a decoration on your bookshelf to make you seem smarter. That's OK. 18. Trainspotting by Irvine Welsh (1993) allstarejeans.blogspot.com Welcome to the grotesque world of Scottish junkies seeking highs all over the city of Edinburgh in the '90s. 19. Sex and the City by Candace Bushnell (1997) fantasticfiction.co.uk The cast of characters — Carrie, Big, Samantha, Miranda, Charlotte — have become American icons. There's nothing better than tales of dating in the '90s.