Author: Michael Chabon
Released: 1995
Genre: Drama

Though The Amazing Adventures of Kavalier and Clay received the most critical accolades, the smaller scope of Wonder Boys allowed Chabon’s gifts as a comic writer to shine. He zeroed in on Grady Tripp (inspired by Chuck Kinder, a writing professor at the University of Pittsburgh, where Chabon did his undergrad work), the hapless writer trapped inside a novel so sprawling that it leaves no character’s dental records undescribed. On top of that, Tripp might be in for a trek through the “elephant-white hills of abortionland,” as he has knocked up the woman he’s creeping with.

There’s also a socially awkward student of Tripp’s, mucking up his day-to-day routine of pot smoking and writing. Then there’s the dead dog, and the beautiful student living in his house. And a jacket of Marilyn Monroe’s that’s gone missing. One of the most humorous and kind portraits of Pittsburgh set to paper, Wonder Boys is that rare book that elicits genuine laughs from the reader. There’s nothing harder than wringing humor from the written word.

Fun Fact: Chabon's novel was adapted by director Curtis Hanson in 2000 into a feature film starring Michael Douglas, Tobey Maguire, and Robert Downey, Jr., and, surprise, it's actually one of Hollywood's most underrated book-to-film translations.