Book
One of my favorite books of all time and in my opinion the greatest comedic masterpiece in fiction, books in general, the world?! This is certainly Wallace’s greatest work and one that is touching, uncomfortable, and all consuming. Set at both a prestigious tennis academy and a halfway house, Wallace takes seemingly impossible to relate to characters and humanizes them with charming and disturbing quirks. His characteristic experimental writing style is rampant and at its best (see: long section of footnotes at end of book), but every pause feels purposeful and adds to the story. I’ll just say that I envy you, you reader of Infinite-Jest-For-The-First-Time, it’s frankly, amazing.