Best Gilmore Girl Episodes to Rewatch During Autumn

Despite a seven-season run that ended nearly 15 years ago and a recent high-profile Netflix revival, Gilmore Girls continues to gain in popularity with every passing year as new generations discover the fast-talking, pop culture-obsessed mother/daughter duo that made an eternal lifestyle out of overdosing on caffeine in small towns where it somehow always feels like autumn. Indeed, the Gilmores have since developed a passionate cult following, maintaining its relevance in the social media and streaming ages thanks in part to its genius one-liners and critically thinking characters. But the best explanation for why Gilmore Girls continues to endure is its realistic and comforting portrayal of young adult life and everything that comes along with it: family, friendship, romance, ambition, and generational divides. And also, lots and lots of coffee.

Since Gilmore Girls manages to retain a permanent autumn aesthetic, legions of fans worldwide enjoy rewatching the series as the chilly weather arrives. Generations aren’t the only thing that cause divides in this universe, since there are plenty of decisions every fan finds themselves having to make with every viewing. Team Dean, Team Jess, or Team Logan? (Or maybe just Team Rory?) What about Luke and Lorelai or Lorelai and Christopher? Or, dare we say it, Lorelai and Jason?

Whatever end of the plot argument you find yourself on, Gilmore Girls always provides a quality mix of humor and tearjerkers. Since so many of us find ourselves consistently drawn back to Stars Hollow, making a list of the best episode from each season that will satisfy everyone is impossible. But nonetheless, here are the 7 best episodes of the series to fuel your autumn rewatch—or better yet, coax new fans into watching for the first time.


“Cinnamon’s Wake” (Season 1, Episode 5)

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Original Airdate: November 2, 2000

Synopsis: As the town of Stars Hollow receives news that Cinnamon, the beloved but elderly cat of Babette (Sally Struthers) and Morey (Ted Rooney), has passed away, everyone joins together for a funeral—much to the chagrin of Lorelai’s (Lauren Graham) mother Emily (Kelly Bishop), who had invited Lorelai to the family funeral of a cousin of whom she has no recollection. (Claudia! Who can forget Claudia?) Meanwhile, Lorelai’s flirtation with her daughter Rory’s (Alexis Bledel) English teacher Max Medina (Scott Cohen) turns into feelings at a Chilton Prep School bake sale, and Rory finds herself in the throes of a flirtation-turned-feelings of her own with Dean (Jared Padalecki), the new kid in town who, judging by the pilot episode alone, is crazy about her.

Why the Episode is the Best: While Gilmore Girls’ inaugural season had multiple memorable moments that would come to influence and inform the remainder of the series, “Cinnamon’s Wake” is what truly introduces us to the small town of Stars Hollow, CT and its quirky inhabitants. How many towns do you know that would band together for a cat’s funeral? To paraphrase Emily when she heard that there had been such a thing, go look up “aneurysm” in the dictionary to see if you had one. The episode also features crucial moments for the two main couples of the season, Lorelai and Max alongside Rory and Dean. What happens next for both pairings is in the eye of the beholder, but as far as “Cinnamon’s Wake” is concerned, we’re hooked.

Best Line: “Stop sweating and close your pores, Kirky. I always forgive. Once,” says Miss Patty (Liz Torres) to Kirk (Sean Gunn), who had interrogated her earlier in the grocery store for eating fresh fruit while shopping.

RELATED: The Best TV Shows to Get You in the Mood for Fall (Sweaters and Cider Optional)

“There’s the Rub” (Season 2, Episode 16)

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Original Airdate: April 9, 2002

Synopsis: After Lorelai is forced into attending a weekend with her mother Emily at a spa where there is no caffeine and only cucumber water, Rory—with the house all to herself—decides it’s the perfect opportunity to both do her laundry the exact way she likes to and order the Indian food her mom hates. Predictably, as perfect solo evening plans usually go, other people in her life manage to ruin her vibe: Chilton frenemy Paris (Liza Weil) arrives unexpectedly, furiously needing a study partner after receiving an (hold for gasp!) A- on an assignment, and before long, Stars Hollow anarchist Jess (Milo Ventimiglia) arrives with a care package from Luke’s diner. Pandemonium ensues further when Dean shows up after Rory insisting she wanted to spend the evening alone. Meanwhile, Lorelai convinces Emily to ditch the spa for a nice steak at a bar, leading to one of many brief moments of peace and reconciliation between the two.

Why the Episode is the Best: Although there are many Season 2 moments between Jess and Rory to choose from, “There’s the Rub” is an essential episode for Jess Mariano fans as it is a rare instance of how he easily loosens up around people he is comfortable with: after Rory insists that Paris stay for dinner to scare Jess off, the three of them end up sharing a meal laced with plenty of pleasant, intellectual conversation. Considering Paris and Jess are two characters known to cause tension and turmoil in Rory’s world, this episode is a nice and brief instance of ceasefire—especially when Paris helps her save face during Dean’s angry outburst. Similarly, when Emily and Lorelai’s dinner at the bar goes awry thanks to a stranger getting too handsy, Emily demands to know why she and Lorelai can’t have the same kind of relationship as Lorelai and Rory. In a spontaneous attempt to bond with her mother, Lorelai convinces them to steal the robes from their hotel rooms, and you like to believe it helped just a little.

Best Line: “Rory and I are best friends, Mom. We are best friends first and mother and daughter second, and you and I are mother and daughter always,” Lorelai tries to explain to Emily why they don’t share the same kind of dynamic as she and Rory.

“Keg! Max!” (Season 3, Episode 19)

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Original Airdate: April 29, 2003

Synopsis: After Lorelai chose to repay the loan from her parents for Rory’s prep school tuition at the end of the previous episode, the Gilmore girls find themselves with their first free Friday night in three years after Emily hastily calls off their weekly dinners in fear of never seeing them without a social obligation. Elsewhere, Lane’s (Keiko Agena) garage band books their first gig at a neighborhood house party, and Jess is informed by the school principal that he has missed too much school to graduate. At the party, Lane realizes that Dave Rygalsky (Adam Brody) is truly in love with her and, having indulged in a few too many cups of beer, drunk-dials her vehemently conservative Korean mother and confesses all her secrets. Despondent over the news that he can’t graduate or take Rory to the Stars Hollow High prom, Jess struggles to communicate and a failed attempt to have sex at the party leads to yelling and tears. Dean, ever-protective of Rory, starts a fight with Jess that destroys the house and further damages Jess’ reputation. Meanwhile, Lorelai runs into Max at a Chilton booster club meeting and old feelings are randomly resurrected.

Why the Episode is the Best: Many fans are always quick to choose the famous dance marathon episode from Season 3 as one of the best episodes, and while it certainly is, “Keg! Max!” is another worthy contender from this season as viewers are allowed insight into the difficulty and severity of Jess’ personal situation, and how it differs largely from the other teenagers around him. While many Gilmore Girls fans are quick to point out that Jess supposedly forced himself on Rory at the party, there was a whirlwind of other emotions at play here that don’t make the incident in Kyle’s bedroom black or white. Most importantly, however, this episode stands out as the physical animosity between Dean and Jess that had been brewing since the early days of Season 2 is finally released, however messily.

Best Line: “Yung Chu, you should probably stay away from the band area. We’ve got a lot of chords and stuff, and I don’t want you to get electrocuted and die,” Dave tells Lane’s fake Korean boyfriend whom he learns has caught feelings for her. He’s lying, Yung Chu. That’s exactly what he wants.

“Girls in Bikinis, Boys Doin’ the Twist” (Season 4, Episode 17)

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Original Airdate: April 13, 2004

Synopsis: Unable to ignore the harsh realities of a Connecticut winter, college roommates Rory and Paris give in and decide to join everyone heading down to Florida for spring break. There, they run into their former Chilton classmates Madeline and Louise (Shelly Cole and Teal Redmann), who show them the ropes of spring break. Through it all, Rory and Paris remain indifferent to the entire experience—even as Paris tries to kiss her in an attempt to join in the “girls gone wild” culture—and much prefer ordering pizza and renting The Power of Myth in their hotel room than engaging in any kind of partying. At a tipsy session of reminiscing with Madeline and Louise, they accidentally-on-purpose dial Dean’s number, prompting a reconnection with significant foreshadowing for what’s to come. Meanwhile, Lorelai reaches a milestone in her relationship with Jason Stiles (Chris Eigeman), who gives her a key to his apartment. But our focus is drawn away from them when Luke (Scott Patterson) suddenly needs Lorelai to bail him out of jail.

Why the Episode is the Best: Season 4 is arguably the strongest season of Gilmore Girls with very few filler episodes, and “Girls in Bikinis, Boys Doin’ the Twist” is a prime example of that. From the series’ trademark introverted humor that finds Rory and Paris disinterested in the party culture of American spring break to containing countless classic moments of Paris Geller being a bitter icon, the episode is Gilmore Girls at its finest: a flawless mix of comedy and drama. Additionally, while Luke and Lorelai are certainly endgame, she and Jason were a strong pairing that allowed us to witness, if only for a moment, Lorelai Gilmore acting like a mature adult with actual communication skills.

Best Line: “No, it’s National Baptism Day,” replies Paris sarcastically to a clueless bystander asking if it’s raining in front of a door with a window, where it is clearly pouring. “Tie your tubes, idiot.”

“Wedding Bell Blues” (Season 5, Episode 13)

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Original Airdate: February 8, 2005

Synopsis: The 100th episode of Gilmore Girls finds Emily and Richard (Edward Herrmann) renewing their vows at an elaborate ceremony after being separated for several months, with Lorelai serving as Maid of Honor and Rory as Best Man. But just as Lorelai once told us, there’s nothing like a family to screw up a family: Rory is angered that her budding romance with Logan Huntzberger (Matt Czuchry) keeps getting interrupted by him seeing other girls, including the one he brought as a date to the vow renewal. But that of course pales in comparison to the storm that is brewing between Luke, Lorelai, and Rory’s father Christopher (David Sutcliffe), who was invited to the event by Emily in order to, unbeknownst to her daughter, win back Lorelai. After a mishap that includes Rory’s parents walking in on her and Logan in a state of undress, Luke asserts that he is the one who has been more of a father figure to Rory than Christopher ever has. Upon learning that it was Emily who caused this chain of events, Lorelai expresses her intentions to permanently sever her mother from her life.

Why the Episode is the Best: While satisfying for viewers to see Emily and Richard reunite after a months-long separation of acting like petulant children, it’s the petulant, childish drama that unfolds between Luke, Lorelai, and Christopher that makes “Wedding Bell Blues” stick out in the memory of fans. While the love triangle would, for better and for worse, make up the romantic action for the remainder of the series, it’s Luke’s response to Christopher’s drunken outburst that confirms and solidifies the dynamic we’ve spent the last five seasons watching. No matter which couple you find yourself a fan of, Luke was always more of a father to Rory than Christopher, and that is not up for debate.

Best Line: “You and me. We’re done,” Lorelai whisper-shouts in her mother’s ear after learning how she tried to sabotage her relationship with Luke. For once, we really can’t blame her.

“Friday Night’s Alright For Fighting” (Season 6, Episode 13)

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Original Airdate: January 31, 2006

Synopsis: After learning from someone who wasn’t Luke that he has a daughter, Lorelai tries to navigate the situation and the impact it’s having on their engagement. Meanwhile, over at the Yale Daily News, concerns over Paris’ lack of proper management skills are mounting as the entire staff threatens to quit—with Rory enlisting Logan to help save the paper. When Lorelai informs her parents that they won’t need to finance Rory’s education any further, resentment and animosity starts to build. At the following Friday Night Dinner, the Gilmores finally have it all out about everything that has gone on in their lives for the first half of the season, and everything that they have not seen eye to eye on. Kiss and make up doesn’t quite cover it, but they manage to leave everything as most families know where it belongs: in the past.

Why the Episode is the Best: Miscommunication is a common theme throughout Gilmore Girls, and there are very few moments outside of “Friday Night’s Alright For Fighting” where characters actually discuss or argue things in a rational or mature way. (Does any family?) While the series had definitely started to lose steam by this point, and we can certainly see the writing on the wall vis-à-vis Lorelai learning that Luke has a daughter and kept it from her, this episode asserts itself as one of the best by merely letting the Gilmores yell it all out.

Best Line: “You have nothing better to do with your time?” Rory asks Logan after learning he’d been hanging around her coffee cart three times a day in order to run into her. “Nothing better than to try and get you back, no,” he replies.

“I’d Rather Be in Philadelphia” (Season 7, Episode 13)

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Original Airdate: February 6, 2007

Synopsis: After Richard collapses at the end of the previous episode, the Gilmores receive unexpected comfort in the form of Luke at the hospital. Lorelai’s husband Christopher is not picking up his phone and has gone MIA after learning that Lorelai wrote a character reference for Luke’s custody hearing, and angrily believes that Luke was Lorelai’s first choice. (He’s not wrong!) Rory also receives unabashed love and support from Logan in the hospital waiting room, perhaps solidifying him as someone who loves and cares for her, if there was still any lingering doubt. When Christopher finally does receive the news, he arrives in time to offer words of sympathy but unfortunately none of support, as he is still angry and resentful of Lorelai for supposedly betraying him.

Why the Episode is the Best: Pretty sure no one has ever used the term “the best” to describe Season 7 of Gilmore Girls, but “I’d Rather Be in Philadelphia” stands out for the emotional connection it forges on both the audience and the characters, reminding us that it’s our real loved ones who will always be there to support us during difficult times. The episode is perhaps among the more decent of the seventh season as it reminds us who has always been there for Lorelai and Rory, and who will always be there for Lorelai and Rory. (Hint: it’s not Logan.)

Best Line: “He’s like Warren Beatty, your dad—or Sean Connery or—who’s that one I always found so sexy? The evil politician with the glasses—Henry Kissinger!” Leave it to Babette to break the tension by comparing Richard to famous men she finds sexy.

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