THE GREAT GATSBY: I refuse to consider Long Island, where much of the novel unfolds, as a part of New York City, but my editor asked me to add this famed F. Scott Fitzgerald novel, so here it is. Nick Carraway—bond salesman, loner, potentially closeted gay man—gets drawn into neighbor Jay Gatsby's opulent, dramatic, and ultimately tragic life, one that exemplifies the devastating pitfall that is the American Dream (or so I wrote in a high school paper once). Though I'd take Tender Is The Night over Gatsby, the latter boasts some of literature's most exquisite prose, and is mandatory whether you're in school or decades out. Or you could watch one of the movies! Just kidding, don't go near either garbage iteration.