Hi everyone! It's been great to see what everyone's come up with so far. My list took me so long to write just because I couldn't narrow it down to just five. Nevertheless, I did it:
F. Scott Fitzgerald, This Side of Paradise. Sure, everyone loves The Great Gatsby, but Fitzgerald's first novel is more raw and sad and charming. I read it in high school and probably re-read it at least once a year.
Judith Kogan, Nothing But The Best. I was a high school orchestra geek and often stayed up nights re-reading this nonfiction book about students and teachers at The Juilliard School, one of the best music conservatories in the country. I was never this good, but I still loved reading about it.
Gordan Korman, No Coins, Please. This middle-grades chapter book about a bunch of boys taking a van trip across the country (and one's plan to make a million dollars, stop by stop) is still one of the funniest books I've ever read.
Margaret Atwood, The Robber Bride. This is a good introduction to the novels of Atwood, who I think is one of the best in describing relationships among female friends both treasured and toxic.
William Shakespeare, Twelfth Night. So what if I've never worn yellow stockings, dressed in drag or had a twin brother? This is my favorite Shakespeare play, hands down, and it doesn't have to be directly relevant to be enormous fun.