20 Best Gilmore Girl Episodes

It's officially fall, which means everyone in the world is basically mandated to watch Gilmore Girls illed with a with its coffee and a cozy fall feeling. I was especially delighted to see that this past week marked the 20th anniversary since the Gilmore Girls pilot premiered on the WB. In honor of this momentous date, I'm ranking the top 20 episodes of the show. I had to make some tough choices. I agonized. I did not put any episodes from season six, seven or the dreaded Seasons on here. I realized that most episode that feature the word "Lorelai" in the title are on this list. I realized I still hold a DEEP nostalgia for season two, which was when I was first introduced to Stars Hollow. For your viewing pleasure (also, spoilers below, but it's been 20 years, watch the show already!!), here are the 20 best episodes:

20. Teach Me Tonight: This episode perfectly encapsulates the magical blend that is Gilmore Girls. Half of the episode is devoted to Rory and Jess flirtation and the fallout after Jess crashes Rory's car, while the other half is Lorelai trying to pick a movie for Stars Hollow movie night. The whole thing ends with several minutes devoted to A Film By Kirk. It's an excellent mixture of teen drama and town quirk.

19. Written in the Stars: It's Luke and Lorelai's first date!!! Yes, his story about the first time they met really doesn't mesh with the previously established timeline but we don't care because he kept the horoscope he gave her in his wallet!!! In other news, Taylor tries to put Lorelai and Luke's relationship to a vote in a town meeting for fear that their eventual breakup will disrupt local business, Rory meets Logan (UGH) and Emily ends up surprising Rory with a visit at Yale.

18. Pilot: I know, I know, this is a shockingly low ranking for what is arguably a very strong pilot episode, but I can't get over the fact that Rory wanted to bail on Chilton to hangout with Dean (in retrospect, this tells us a lot about Rory). Besides that annoying factor, the show's first episode does a couple truly REMARKABLE things -- it establishes Rory/Lorelai's bond from the opening moments, as well as two plot points that carry through the first four seasons of the show: Lorelai wants Rory to go to Harvard and Lorelai and Sookie want to start their own inn). The pilot also creates the Friday night dinner tradition that carries on throughout for the ENTIRE SERIES.

17. Last Week Fights, This Week Tights: This episode is most memorable for Lorelai and Luke's first dance ("Luke can waltz? Luke can WALTZ."), but when you look at the entire 40 minutes, it's again an example of the balance between quirk and drama that makes this show so memorable. Liz and TJ get married in a renaissance fair themed evening. Luke follows the advice of a self-help book and finally asks Lorelai out. He then gives that self-help book to Jess, who learns that he should thank Luke for all he's done (good progress) and then asks Rory to run away with him (overkill). Rory is set up by her grandmother with a dud and then calls Dean to come pick her up (yawn). Lane and Mrs. Kim make amends over a delightfully awkward dinner party. And did I mention the dance??

16. A-Tiskit, A-Tasket: An entire episode that centers around a town festival? I'm in. This mid-season two segment features more Rory/Dean/Jess drama, when Jess outbids Dean for Rory's picnic basket and Rory's true feelings are semi-exposed when she agrees to go to lunch with him. Ms. Patty, out of an abundance of love, tries to set Lorelai up with a man, and she rushes to Luke's to get him to bid on her basket instead. Poor Lane experiences her first taste of heartbreak, when her plans to have the boy she likes sneak by her house prove too much.

15. Those are Strings, Pinocchio: I can't get through the season three finale without crying, no matter how many rewatches I do! It's a turning point for our Gilmore girls and so much of what is set up in the pilot comes to pass -- Sookie and Lorelai finally get their own property to start an inn and Rory graduates high school and is off to the Ivy League (just not the one she originally thought). And yeah, yeah, Rory's graduation speech isn't really for her entire graduating class -- it's mostly all about her (classic Rory) -- but come on: "My mother never gave me any idea that I couldn’t do whatever I wanted to do or be whomever I wanted to be. She filled our house with love and fun and books and music, unflagging in her efforts to give me role models from Jane Austen to Eudora Welty to Patti Smith. As she guided me through these incredible eighteen years, I don’t know if she ever realized that the person I most wanted to be was her." I honestly got teary just re-reading that.

14. Let the Games Begin: It's the morning after the Dance Marathon (and we'll get to that in spot number four), and Rory/Jess are now a thing, Kirk is bringing is trophy around town and the Gilmore girls are sucked into a family road trip to Yale. Richard and Emily share cute stories on campus and Emily and Lorelai bond, but it all comes to a halt when Richard springs a surprise admissions interview on the three women and everyone leaves in a huff.

13. Kiss & Tell: A quintessential fall episode! The town is covered in leaves and pilgrim costumes (it's New England, after all...), and Dean kisses Rory in the market!! Rory gets scared to tell her Lorelai, who ends of finding out from other town sources. In a misguided effort to let Rory know she's totally cool with it, Lorelai invites Dean to join them at movie night. While Willy Wonka & the Chocolate Factory plays, Dean and Rory bond and Dean and Lorelai do too.

12. Like Mother, Like Daughter: Now that Rory has been at Chilton for about a year, these private school teachers start to pick apart her social life. After getting told she needs to start socializing more with the other students, Rory accidentally befriends "The Puffs," a secret society. Obviously, things go downhill from here. The Chilton staff come after the elder Lorelai too! They make her join the Booster Club, and Lorelai ends up hosting a mother/daughter fashion show at the inn. It all ends with Lorelai and Emily dancing down the runway in matching outfits.

11. The Festival of Living Art: This episode earned Gilmore Girls its only Emmy win (for outstanding makeup -- honestly the NERVE), because of the iconic Festival of Living Art. Lorelai fights to star in the Renoir, Rory is selected for an original painting, Sookie goes into labor and Lane, Brian and Zach find their new guitarist. Not only does this episode feature a number of great plot points and funny lines, but the way they recreate the paintings for the festival is truly beautiful.

10. A Deep-Fried Korean Thanksgiving: It's the first time the Gilmore family reunites since the drama at Yale in Let the Games Begin and it obviously goes poorly when Rory admits she has applied to Yale. Rory and Lorelai try to pack four Thanksgiving gatherings into one day, and they spend the episode moving from Sookie and Jackson's place to the Kim's to Luke's to Emily and Richard's house. It's a true test of their eating skills! Meanwhile, Lane and Dave share their first kiss!

9. It Should've Been Lorelai: Paris and Rory prepare for a debate at school, and Christopher decides to show up to actually support her for once. He brings his new girlfriend, Sherry, without warning anyone, and Sherry is ready to BOND with Rory. In addition to some funny Paris comedy moments, this episode features a classic Emily/Lorelai argument, as both Gilmores realize Christopher is finally getting his life together with another woman.

8. Lorelai's Graduation Day: It's the penultimate episode of season two, and WHEW is there a lot going on. Lorelai is graduating from community college and Rory takes it upon herself to let Richard and Emily know. Richard and Emily show up to the ceremony (and look SO PROUD when Lorelai walks across the stage... it's beautiful), but Rory misses the whole thing because she took a poorly timed bus to NYC to visit Jess... Also, Seth MacFarlane guest stars.

7. The Incredible Sinking Lorelai's: I'm going to be honest, I think I've only watched this season four episode three times, because it makes me anxious. Season four of the show is a brilliantly plotted season of TV. This midway point shows Lorelai and Rory struggling, and it's one of the few episodes in the entire show where Lorelai and Rory don't speak or share any scenes together. Lorelai is rushing around trying to get things ready for the launch of her inn, but she's running very low on money. Rory is trying to take too many classes at Yale and finds herself unable to keep up. They both keep calling and leaving voicemails for each other but can't get on the same page to talk. It's powerful because it's rare to see the Gilmore girls floundering without each other to lean on.

6. The Lorelai's First Day at Yale: Another tear jerker! Rory is off to college and while she and Lorelai are initially caught up in the whole move-in process, they both realize that big changes are happening. Paris reappears. Luke helps dispose of a mattress. Rory makes Lorelai come back to school because she misses her. And Lorelai ends the episode all alone, after Rory officially leaves for school. TEARS.

5. Rory's Birthday Parties: It's only the show's sixth episode but it sets up a dynamic between Lorelai, Rory, Richard and Emily that extends throughout the series. Rory's bday lands on a Friday night dinner, and Emily insists on throwing her a fancy party. Emily invites all of the Chilton classmates that Rory despises, and after Rory yells at Emily, Lorelai is the one trying to bring the family together. The grandparents end up showing up in Stars Hollow for Rory's second birthday party with the rest of the town. At the end of the evening, Emily leaves saddened, as she realizes she doesn't know Rory or Lorelai at all. Not only does it give some great moments of character development, it's also a brilliant juxtaposition between the next birthday party that Emily will throw for Rory in season six.

4. They Shoot Gilmores, Don't They?: It's the famous dance marathon!! This episode feels like a musical at times, which is no surprise because it's directed by the brilliant Kenny Ortega. Lorelai is on the hunt for a winning dance partner who can help her beat Kirk for the first time ever and ends up forcing Rory to join her team. Everyone in town is dressed up for the occasion, and it naturally leads to a Rory/Jess/Dean fight, a Luke/Lorelai moment of bonding and some hilarious moments from the townies.

3. The Bracebridge Dinner: Another town event! When a snowstorm hits and a big group that was supposed to come to Stars Hollow has to cancel, Lorelai and Sookie host the town (plus Emily and Richard) at the Independence Inn to feast and enjoy horse-drawn carriage rides. It's cozy and festive and filled with fun.

2. I Can't Get Started: It's Sookie and Jackson's wedding day in this season two finale! Jess returns to town and is greeted by an enthusiastic Rory. Christopher and Lorelai reunite, only to have everything come crashing down when Sherry announces she's pregnant. Emily and Richard are happy for now, and Paris and Rory win the class election.

1. Raincoats and Recipes: This is a perfect, perfect episode of TV. It's the season four finale and the Dragonfly Inn is finally opening!! Lorelai and Sookie host the whole town (plus Richard and Emily) for a test run. Jason shows up unannounced, Luke and Lorelai share their first kiss, Dean and Rory... I honestly can't even get into that, Richard and Emily argue, Kirk is naked and Lorelai and Sookie finally achieve what they've been dreaming of since the pilot. It's filled with the a fine mix of comedy and drama, with pitch perfect writing, directing and acting.