10 Most Iconic Books on Gilmore Girls That Live Rent Free in Our Heads

It's a lifestyle. It's a religion. And it's a haven for book lovers!

Gilmore Girls is not just “a lifestyle, a religion,” like The Donna Reed Show. It’s also a haven where book lovers can celebrate their love of the written word through its 500+ book references.

Here, I’m breaking down ten of the most iconic of them all. These books are not just classics— they’re also classics famously read and/or referenced by the Gilmores.

When you click through the title links below, you’ll find my full book review pages on the Friday Night Readers website for each of them, filled with quotes, pairings, multimedia, tips, and more details about each time they were referenced on the show.

I’m working on creating a page like this for each of the books from the show I’ve read to create the ultimate Gilmore Girls reading resource for you. These are the first 10!

10 Most Iconic Books Featured on Gilmore Girls

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Anna Karenina by Leo Tolstoy

Anna Karenina is widely regarded as Rory Gilmore’s favorite book, though Dean called it “depressing” and “over [his] head.” Of course it was.

And in her Chilton speech, Rory famously says she “rode a sad train with Anna Karenina.”

This 800+ page Russian classic is long and hard, but worth it, from its famous opening line (“All happy families are alike; each unhappy family is unhappy in its own way.”), which Luke misquotes, through its dense chapters about agriculture, to its tragic conclusion.

I’m with Rory, who quipped back to Dean that it was “beautiful.”

The Bell Jar by Sylvia Plath

The Bell Jar is NOT the book Rory famously reads at the bus stop. That’s The Unabridged Journals of Sylvia Plath.

But it’s repeatedly shown with Rory: at the book sale, in her room, and in her drawer. Lorelai also refers to it to Rory, implying she knows it’s one of Rory’s favorites.

Like Plath’s Esther Greenwood, Rory Gilmore is ambitious and driven and seeks a career in journalism. Esther's struggles foreshadow that Rory's dreams may not be as easily achieved as she believed earlier in the Gilmore Girls series.

Driving Miss Daisy by Alfred Uhry

Driving Miss Daisy gives us one of the most memorable images of Emily Gilmore across all seasons: lying back on the couch in dark sunglasses, demanding Lorelai chauffeur her around after minor eye surgery. Has anything ever been more Emily?!

This is one of the most heartwarming books I’ve read and a perpetual favorite of book club members taking our Rory Gilmore Reading Challenge. It’s a play you can read in just over an hour!

Take the Rory Gilmore Reading Challenge 2025 (Pt. 2!)

Howl by Allen Ginsberg

Howl is “the Jess book.” It’s the one he borrows from Rory’s bookshelf, it’s the one in which he writes in the margins, and it’s the one he tells her he read “about 40 times" during their first meeting, cementing their literary bond.

It’s so brief you can read it in about an hour; though, since it’s poetry, a few rereads may prove worthwhile. It captures the Beat Generation’s American post World War II sentiments without sugar coating.

Mrs. Dalloway by Virginia Woolf

Mrs. Dalloway is one of the books Rory is famously seen actually reading on the show — this time at her grandparents’ home with the cherubic grin of a literature student.

(Note: What Rory “actually” read is always a hot debate.)

Rory’s reading of it is evidence of her love of both classics and books about feminism, which she often reads throughout the show.

A Moveable Feast by Ernest Hemingway

A Moveable Feast is Ernest Hemingway’s memoir about his early years as a struggling writer in Paris, featuring the likes of F. Scott Fitzgerald as companions. Think: Midnight in Paris. It has the most delectable sense of time and place.

I wanted to include a book Rory herself physically read on the show in the context of her Logan years (Team Logan) at Yale, and this one is it.

Hemingway says:

“If you are lucky enough to have lived in Paris as a young man, then wherever you go for the rest of your life, it stays with you, for Paris is a moveable feast.”

And we can say the same about Logan, too, can’t we?!

The Outsiders by S.E. Hinton

The Outsiders references are scant, yet so iconic in Gilmore Girls. Dean calls Rory Ponyboy in “the dance” episode, and Lorelai calls her a Soc when she gets hazed by the Puffs.

These subtle literary delights are a big part of what I love about reading the books on the show. It’s not about titles or book covers. It’s a holistic literary and pop culture-based understanding of classic works.

Pride and Prejudice by Jane Austen

Pride and Prejudice is the classic romance novel that Dean read to bond with Rory. Say what you want about Dean, but he tried.

And the fact that he enjoyed it bridged a gap in their personalities and further united them in their own love story in its early days.

Of course, we can also thank Max Medina for sharing the Austen wealth throughout Rory’s Chilton years.

Romeo and Juliet by William Shakespeare

Romeo and Juliet was meant to bring Rory and Tristin together, but after he was sent away to military school, all we were left with was Paris’s “Thus, with a kiss, I die,” over Rory’s splayed body.

Since Rory’s education is a central theme on the show, it's fitting that such an iconic play was represented so memorably.

The Year of Magical Thinking by Joan Didion

The Year of Magical Thinking is never actually discussed on Gilmore Girls, but Rory famously reads it on the couch on Martha’s Vineyard. This grief memoir is not exactly a beach read, but that’s Rory for you!

Rory’s choosing such a popular, award-winning book at the time of the show shows exactly how engrossed her character is in current literary culture.

Let’s manifest a Stars Hollow fall starting now.

Which Gilmore Girls book reference was most iconic to you?

P.S. - Want more like this? I shared my top 6 book recommendations for Gilmore Girls fans on the What to Read Next podcast today, so check it out!

Laura Yamin

and I couldn’t stop gushing. This is all exactly the type of content I’m focusing on moving forward at Friday Night Readers, so if you love books and Gilmore Girls as much as I do, then tune in!