Over 300 books (and probably even more authors) are mentioned on Gilmore Girls. Many of the characters are well-versed in literature, television, film, music, and other aspects of popular culture, and it's normal for Rory to discuss books regularly with family, friends, and love interests in a typical episode.
Dean tries to be a good sport and read Pride and Prejudice, but Jess is the boyfriend who can keep up with Rory's quick reading pace. Rory and Jess could fill their own library, and there would be no shortage of creative selections.
Charles Dickens - Oliver Twist
Oliver Twist is the least pretentious of Rory and Jess's literary references, but this is not to say that Dickens is easy to crack, in general. Rather, Oliver Twist is a story that readers of all ages can comprehend at least a summary of.
The plot has been translated to many mediums, and the orphaned Oliver even seems fitting for Jess's character. Though he hasn't lost his parents, he spends a large amount of time without them while he lives with Luke.
J.D. Salinger - Franny And Zooey
J.D. Salinger wrote about his title characters separately in the 1950s - Franny's story was a short story and Zooey's was a novella. A couple weeks after Jess pockets Rory's special Dean bracelet in season two, Lorelai catches him coming out of Rory's room while he is at the house to do yard work.
To cover up the fact that he was actually in the room returning the bracelet, Jess says he wanted to make sure Rory had Franny and Zooey. He chose a great book for his quick line, too since Salinger opens the novel talking about a Yale game.
Ernest Hemingway
When Rory wants Jess to immerse himself in Ayn Rand in season two, Jess wants Rory to commit to the works of Ernest Hemingway. Hemingway is a classic American author who was friends with F. Scott and Zelda Fitzgerald.
Avid readers know Hemingway for The Old Man and the Sea, The Sun Also Rises, For Whom the Bell Tolls, A Moveable Feast, A Farewell to Arms, and countless other works. It makes sense that Jess would like Ernest Hemingway's no-nonsense style of telling a story.
William Shakespeare - Othello
When Rory starts tutoring Jess at Luke's request, Jess wants to do anything but study. He persuades Rory to go with him to get ice cream in season two's "Teach Me Tonight," and Rory agrees. She tells Jess to drive the car while she reads Othello. This is Rory's idea of a fun time.
Othello is one of Shakespeare's most suspenseful works as it delves into Desdemona's fate after she cheats on Othello. This text is fairly accessible and is standard fare for a high school English class.
Mary Shelley - Frankenstein
High schoolers also might read Frankenstein by Mary Shelley. Jess references the young scientist's scowl in season two.
It's all too easy to mistake the scientist for the famous monster image perpetuated by Halloween and by Hollywood, but it really is Frankenstein's monster, not Frankenstein the monster. This is a great book for Jess to mention, in any event.
Gabriel García Márquez - One Hundred Years Of Solitude
Jess reads García Márquez's One Hundred Years of Solitude as he travels away from Rory to California in season three. Rory gets onto the bus and joins Jess in the back while toting a book of her own, Blanche Wiesen Cook's Eleanor Roosevelt.
One Hundred Years of Solitude focuses on the patriarch of the Buendía family, the owners of the fictional town of Macondo. Rory doesn't know that Jess is leaving, but the solitude soon sets in.
Allen Ginsburg - Howl
When Jess is introduced in season two, viewers quickly see that he and Rory will bond over literature. They both have an affinity for the Beat Poets, so when Jess gets a look at Rory's bookshelf while she's not in her room, he swipes an Allen Ginsburg poetry book containing "Howl" and returns it with his own annotations.
"Howl" is a bit pretentious in that it requires some background knowledge of the Beat Poets and their spontaneous style. Ginsburg himself called his poem "an emotional time bomb that would continue exploding … the military-industrial-nationalistic complex."
Jack Kerouac & Charles Bukowksi
Selected works aren't examined in detail, but Jack Kerouac and Charles Bukowski are brought into Rory and Jess's long-running Beat conversation. Kerouac especially is associated with Allen Ginsberg, but Paris, Rory, and Jess bring him up in the same conversation as Charles Bukowski, a prolific writer who focused on "a depraved metropolitan environment, downtrodden members of American society, direct language, violence, and sexual imagery."
To further complicate their heated author discussion, the Gilmore Girls characters also throw in Franz Kafka and Jane Austen.
Kurt Vonnegut - Slaughterhouse Five
It takes a lot of focus for Jess to read Kurt Vonnegut's Slaughterhouse Five in season two. The science-fiction novel is an anti-war piece that draws on Vonnegut's own experiences in the US Army in Dresden.
Vonnegut doesn't shy away from violence or profanity, and Jess is both strong and serious enough to read such a novel, even while developing his friendship with Rory.
Ayn Rand - The Fountainhead
As Rory and Jess start to become closer, their literary conversations continue and expand. The Fountainhead is Rory's pick for Jess after he bids on her basket in the fabled "A-Tisket, A-Tasket" episode. Rand coined the philosophical system of objectivism, which is built on reality, reason, self-interest, and capitalism. Twelve publishers first rejected The Fountainhead as "too intellectual."
Jess does not care for The Fountainhead whatsoever and does not align politically with Rand. Rory convinces him to give the book one more try by the end of the episode.