On the Road by Jack Kerouac
Kerouac’s agent spent more than four years trying to find a publisher for this turbo-charged, road-trip novel about the postwar beat generation. Finally published in 1957, On the Road—written in a style at once breathless and disjointed—spoke to the deep restlessness of young people chafing at mainstream Cold War culture. Also give these best autobiographies ever written a read.
Tell Me a Riddle by Tillie Olsen
You might not have heard of Olsen, but her 1961 story collection Tell Me a Riddle was one of the first to intimately chronicle the lives of working-class women. One entry is plainly titled “I Stand Here Ironing,” and chronicles a mother’s regrets with wisdom, bravery, and not an ounce of self-pity. Olsen opened a window onto a world not often seen before in American literature and influenced a generation of women writers, including Margaret Atwood, Sandra Cisneros, and Alice Walker. Here are some great books for mothers and daughters to read together.
Great Expectations by Charles Dickens
You might’ve been assigned the tale of Pip the ambitious orphan in school. But we promise Great Expectations is a good book to read as an adult, because the humor that sailed over your head as a kid will be evident now—and besides, you won’t need to write a paper about it. Dickens, in his time, was as famous as a rock star (or, a Kardashian) because his novels were written as page-turners, with whip-smart observations about ambition and human nature.