Cinnamon’s Wake (Season 1, Episode 5)
Nerdy Spice: This episode is a close second in my heart after “Love, Daisies and Troubadours.” The episode revolves around the death of a beloved neighborhood pet, Babette’s cat Cinnamon, so Stars Hollow quirk is on full display as everyone from Luke to Sookie helps out with the wake. But the real magic is in Rory and Dean’s budding romance. Rory couldn’t be cuter when she panics and yells to the bus driver that Dean needs to get off, because the bus is going to Hartford. “You’re forgetting something. Buses have stops,” he teases her as he leaves her in complete, rolling-eyes-at-self confusion. Then, when her shyness starts to seem like disinterest, it takes him promising to leave her alone before she finally works up the courage to announce that she is interested… and then panic and run away. Dean clearly thinks it’s adorable, and I agree.
Janes: The first season had its share of awkward moments while the writers and actors were still discovering the characters we all know and love: Rory’s voice was super low, Emily dressed far too frumpily for her eventual personality, Kirk’s name was “Mick,” Rory and Lorelai keep insisting that they never fight even as they literally fight all the time, and Lorelai ate a salad at one point. A SALAD. But through those growing pains, there were a few standout episodes that made all of us fall in love with the Gilmore Girls, starting with “Cinnamon’s Wake.” The cat funeral gags are hilarious, Lorelai’s burgeoning relationship with Max is light and witty, and most importantly, Rory is painfully awkward with Dean in the best way possible. For any of us who were shy and/or nerdy in high school, Rory’s spastic attempts to interact with the cute boy from the grocery store are way too relatable.
The Break-Up, Part II (Season 1, Episode 17)
Janes: If “Cinnamon’s Wake” is Gilmore Girls’ ultimate celebration of young love, “The Break-Up, Part II” is their ultimate guide to first heartbreak. Lorelai was never wiser than when she told Rory that the ever-important first step in the post-breakup healing process is the wallow: that day (or week, or month) when you don’t shave your legs, order way too much pizza, eat raw cookie dough (because the universe wouldn’t dare give you salmonella on the same day you get dumped), and, of course, watch embarrassingly sappy movies. Rory’s futile attempt to fast-track the healing process was incredibly sad but never maudlin, and Alexis Bledel, who is notoriously terrible at crying (see that unintentionally hilarious therapy session in season six) unexpectedly kills it in this episode, breaking all of our hearts when she finally tells Lorelai with a tub of Cherry Garcia on her lap, “I’m ready to wallow now.” This episode taught a generation of young people how to handle a breakup, but instead of watching Love Story, An Affair to Remember, or Ishtar while we wallow, we can just watch Gilmore Girls.
Love, Daisies and Troubadours (Season 1, Episode 21)
Nerdy Spice: To me, this episode–where Rory reunites with Dean, Max proposes to Lorelai with a thousand yellow daisies, and Mystique Troubadour throws down with Kinko’s Troubadour–is the ultimate Gilmore Girls episode. It has emotional weight–Rachel calls out Luke on his long-denied feelings for Lorelai, and Rory spends the early part of the episode struggling with how to express her feelings after being raised by a woman who often uses the sheer volume and speed of her words to keep men from getting too close to her emotional core. But it also has moments of absolute, giddy delight: Lorelai receives a thousand yellow daisies from Max, and begins spreading them around town, including to Luke, which is pretty much a metaphor of where her affections really lie: Stars Hollow first, Luke second, with Max approximately twentieth, somewhere between Kirk and Taylor. Rory and Dean have an absolutely adorable melodramatic reunion (“I love you, you idiot!”) followed by All the Kissing. The episode ends with Rory and Lorelai jumping up and down in glee in the middle of Stars Hollow, sharing their news. I can’t think of another episode of TV that had that much magic.
The Bracebridge Dinner (Season 2, Episode 10)
Nerdy Spice: Gilmore Girls and snow have always had a special relationship, so it’s hard to pick just one snow-based episode for this list. There’s Season 1’s “Love and War and Snow,” where Lorelai explains her love of snow to Luke (and listens over and over again to Max Medina’s silly voicemail, which never fails to make me laugh: “Lorelai, it’s Max. Medina. Maaax Medina.”). There’s Season 5’s “Women of Questionable Morals,” where the town reenactment gets a naughty update, and Luke builds Lorelai her own skating rink to get her to fall back in love with snow. But I have to pick “The Bracebridge Dinner,” where a snowed-out event leads Lorelai to host a special medieval-themed winter dinner for all of her friends at the Independence Inn. The medieval theme leads to a golden moment where Kirk has to try to maintain his medieval character in the face of an in-depth discussion of I Love Lucy. But the best part is definitely when some of the show’s best couples–Luke and Lorelai, Rory and Jess, and Emily and Richard–take sleigh rides in the snow.
Janes: “The Bracebridge Dinner” showcases so many of the things Gilmore Girls does best: love letters to snow (see above), small-town charm, quippy humor, and, of course, love triangles. This episode had several classic jokes, including Lorelai leaving the picture of the Ugly Baby in Rory’s bed, Babette’s reaction to Mrs. Kim asking if they had engaged in “silent Grace,” and Rory’s description of Paris’ sleeping patterns (“I think she periodically makes a whirring noise and just shuts down” [Nerdy Spice: OMG yes. I have quoted it about many an intense coworker.]). It had the quaintest town event this side of Bid-a-Basket, complete with old-timey speech and horse-drawn carriages, and it was the first episode to kick the Rory/Dean/Jess triangle into high gear. But most importantly, it reminded us that Lorelai and Rory are two of the most distinctive and lovable characters ever to grace our televisions. They watch Godfather III just to hear Frank Coppola’s justification for casting Sofia, they make fun of cliched Christmas cards because they’re “unapologetic mockers,” and they build a snowman that looks like Bjork. As Jess says in the episode, their smirking snowman had the “most personality” because they have the most personality (and while we don’t condone vigilantism, their snowman definitely should have won anyway).
They Shoot Gilmores, Don’t They? (Season 3, Episode 7)
Janes: Speaking of classic town events, no list would be complete without the dance marathon. Every scene in “They Shoot Gilmores, Don’t They,” where Rory and Lorelai compete in a 24-hour dance marathon while Jess and Dean watch from the sidelines, is sparkling with wit–from Lorelai’s horrifyingly awkward interactions with Stanley Appleman and his wife, to Lorelai telling Rory to imagine Al wearing “assless chaps,” to Mrs. Kim handing out tooth-chipping egg salad sandwiches along with “you’re all going to hell” pamphlets. And then it all culminates in Dean (finally) breaking up with Rory in dramatic and public fashion while Kirk runs around the dance floor to the theme of “Rocky,” and then Rory and Jess confessing their feelings for each other on the bridge where it all began in “A-Tisket, A-Tasket.” Plus, the 40s-style costumes were on-point. That helps, too.
Let the Games Begin (Season 3, Episode 8)
Janes: In “Let the Games Begin,” Rory visits Yale with her grandparents, and her relationship with Jess gets underway. The trip to Yale is classic Gilmore family drama, starting with Richard and Emily adorably throwing each other under the bus while telling their “how we met” story and ending with some old-fashioned manipulation and a vicious fight between Lorelai and Richard, then Lorelai and Emily, then Rory and Richard (and a little Richard and Emily, just for good measure). But really, this episode makes the list for Rory and Jess: The Early Years. If you’re a shipper, then you’ll appreciate their innocently awkward first attempt to make out in Luke’s apartment and their considerably more successful makeout set to “Then She Appeared” by XTC. And even if you’re not a shipper, anyone can appreciate the sheer comedic gold of the “hi hi hi” scene (above), especially Lorelai and Luke’s hilariously bemused faces.
Dear Emily and Richard (Season 3, Episode 13)
Janes: Gilmore Girls is, overall, a lighthearted show, and occasionally seems to exist in a parallel universe where death, war, politics, and other types of ugliness can’t quite penetrate. So it’s easy to forget sometimes that the premise on which the show is based is fairly tragic: a young girl with a bright future had an accidental pregnancy, was abandoned by the father, was homeless for a while, and felt so alone in the world that she couldn’t turn to her family for help. The pathos of this story first hits home earlier in the show, when we see the sad little tool shed where Lorelai and Rory lived for a while (although the rosebud wallpaper and pretty water helped), but “Dear Emily and Richard” really hammers it into you. In this episode, flashbacks show the whole story of Lorelai’s pregnancy, while in the present day, Lorelai happens to be present for the birth of Rory’s half-sister, Christopher’s daughter with another woman. For the first time, we get to see for ourselves the acute loneliness of Lorelai’s childhood and pregnancy; the image of Lorelai sitting by herself in the hospital, in labor, listening to “99 Luftballoons” on her Walkman, is one of the saddest in the whole series.
Raincoats & Recipes (Season 4, Episode 22)
Nerdy Spice: Tough to put together a top episodes list without the episode that ends with a long-awaited first kiss between Luke and Lorelai. Lorelai’s getting ready to have everyone in Stars Hollow do a “test run” of her new inn, including Luke, who she suspects she’s accidentally-sort-of dating. It pays off in three hilarious scenes where she bumps into things or outright falls in front of him, and then in a final scene where they hash it out and kiss. Other highlights include the introduction of Kirk’s night terrors, which always lead to him running down the street completely naked; Rory learning that the wages of sin is hearing your boyfriend’s wife answer his phone; and Emily and Richard finally admitting that they’re separated after Lorelai fiendishly makes them stay in an isolated romantic suite.
Friday Night’s Alright for Fighting (Season 6, Episode 13)
Nerdy Spice: This episode starts out lame, with a storyline about Rory trying to get the Franklin out despite Paris having a meltdown, and Logan saving the day–and then culminates with an absolutely bananas Friday night dinner at the Gilmores’. There’s definitely some sexist stuff in the Rory/Logan parts — not only Logan jumping in to save the day on the newspaper even though smart, competent, organized, powerful Rory would easily have been able to do it on her own (see below) but also Logan saying weird things about how being devoted to Rory makes him a “wuss”… seriously?! But the final sequence, the traditional Friday night dinner, is an absolutely brilliant sequence where the Gilmore clan gets to air out all their dirty laundry with each other, from Rory moving out of Emily and Richard’s house without telling them earlier that season, to the oldie-but-goodie “When you get pregnant you get married! A child needs a mother AND a father!” Interspersed with scenes where everyone is so exhausted from fighting that they manage to be friendly with each other, or they just collapse in silence on the couch. It’s fabulous. I am also partial, in a sad way, to the beginning of the episode, where Luke catches Lorelai on her way out to see some florists for their recently-postponed wedding. You can see so much emotion in Lorelai’s face as she tries to pretend she’s fine with postponing: she’s a woman who’s never been very good at selflessness, and yet she bends over backward to be agreeable because she so desperately wants to deserve the love of her life, who’s been unendingly patient with her.
Janes: I hate the Rory/Logan portion of this episode with every fiber of my being. Their reunion was already anticlimactic to begin with, and it was made even worse by Logan’s smug, supercilious efforts to ride in on his white horse. It begins with Logan presuming to take over everything even though he hasn’t been to the paper in months, continues with Logan saying “so this is what hard work feels like” with a smirk on his face, and ends with Rory literally jumping into his arms after he saves the day (not through his own ingenuity, but using his wealth and privilege).
And yet, even “Rogan” can’t ruin the last act of this episode, which were by far the most stylistically ambitious twenty minutes this show has ever produced. The editing is brilliant, the writing is hilariously sharp (“I only wish I hadn’t forgotten to call her a cocktail waitress.” “That’s my mother’s version of the C-word”), and the tonal shifts show an enormous amount of creative control, perfectly transitioning from knock-down drag-out fights to drunken laughter to somber confessions and back to fighting again. The entire act is so cinematic and thematically on-point, it could have served as a proof-of-concept for the series, or just a short film about the most charming yet dysfunctional family you’ll ever see.
Farewell, My Pet (Season 7, Episode 14)
Nerdy Spice: Season 7, when Amy Sherman-Palladino had been tragically removed from her show’s helm, has its dismal moments. But “Farewell, My Pet,” when Lorelai and Christopher finally admit that their marriage isn’t working, is one of the most moving episodes in any season. When Lorelai breaks down and admits, “You’re the man I want to want,” I cry too. Zach does a bang-up job playing “My Heart Will Go On” to bid farewell to Michel’s beloved Chin-Chin, too. And Rory’s incompetent flirtation with her cute professor never fails to make me giggle.
Janes: I go back and forth about whether to consider season 7 part of the true Gilmore Girls canon. But if there is one episode that could justify keeping it, it’s “Farewell, My Pet.” Too many shows romanticize relationships that have terminally bad timing; they would have been soulmates, these shows would have us believe, but the timing renders them tragic star-crossed lovers. But with the painful dissolution of Lorelai and Chris’ marriage, Gilmore Girls acknowledged that in real life, people who can’t make it work over many years are usually just not right for each other. After years of expectation and fantasies of becoming a “normal” family, Lorelai and Chris’ quiet, sad admission that they were never meant to be together is heartbreaking. And yes, like Nerdy Spice, I cry every time I hear Lauren Graham say, “You’re the man I want to want.” That scene single-handedly makes Lorelai and Chris’ rushed, underdeveloped marriage worth it, and reminds us that it’s a bona fide crime Lauren Graham was never nominated for an Emmy.