This is the book Jess is reading when his girlfriend arrives to meet him.
A Confederacy of Dunces is a picaresque novel by John Kennedy Toole, written in 1963 but published in 1980, eleven years after Toole’s death by suicide. It became a cult classic, then a mainstream success, winning the Pulitzer Prize for Fiction in 1981. The title refers to an epigram from Jonathan Swift’s essay, Thoughts on Various Subjects, Moral and Diverting: “When a true genius appears in the world, you may know him by this sign, that the dunces are all in confederacy against him.”
The protagonist of the novel is Ignatius J. Reilly, an educated but lazy thirty-year-old man living with his mother in the Uptown district of New Orleans in the early 1960s. He has been called a modern Don Quixote, an eccentric and idealistic slob who disdains pop culture, and believes that his numerous failings are the working of a higher power. Due to a car accident his mother gets in, Ignatius must work for the first time in many years to pay off her damages bill, moving from one low-paid job to another and having various adventures with colourful characters in the French Quarter of the city.
The novel is famous for its rich depiction of New Orleans and its dialects, many locals seeing it as the best and most accurate fictional depiction of the city. A bronze statue of Ignatius J. Reilly is on Canal Street in New Orleans. It has been adapted for the stage, including as a musical comedy, and has often been planned as a film. These various attempts to adapt it for the screen have come to nothing (often with the slated lead actor dying, and once with a studio head being murdered, not to mention Hurricane Katrina devastating New Orleans in 2005), leading to the belief there is a “curse” on it as a film project.
The novel’s title is a comment on how Rory and Lorelai see Jess and his girlfriend in this scene, as a pair of “dunces” who can barely hold a conversation together. However, it is also believable as a modern American classic that Jess might read, complete with a male protagonist who is an intelligent failure railing against the world, his fate, and modern life. This seems to be the sort of hero that Jess can relate to. Note that it’s also set in the American South – a literary setting which Rory is also drawn to, underlining how much they have in common.