Well, it’s official: Gilmore Girls turns 25 this year. Yep, the show that convinced an entire generation they could survive on nothing but coffee, Pop-Tarts, and obscure movie references first premiered in 2000. And somehow, two and a half decades later, we’re still arguing over which Gilmore guy was the worst, whether Stars Hollow was cute or a waking nightmare, and if Rory deserves defending (spoiler: she doesn’t).
Rewatching it now feels like opening a time capsule. On one hand, it’s comforting, like an autumnal weighted blanket — small town festivals, Lorelai (Lauren Graham) mainlining caffeine from Luke’s diner, Melissa McCarthy before Hollywood turned her into a comedy titan.
On the other hand, with adult eyes? The cracks are glaring. Like, Dean (Jared Padalecki) was never that nice. Logan (Matt Czuchry) was never that deep. And our once-perfect Rory Gilmore (Alexis Bledel)? Absolute menace in a pleated miniskirt.
So in honour of the show’s 25th, here’s the only ranking that matters. Who was the worst?:
14. Dave Rygalski
He set the bar too high. Adam Brody’s Dave was around for literally a handful of episodes before bolting for The O.C., but in that short time, he actually respected Lane (Keiko Agena), learned all of Mrs Kim’s (Emily Kuroda) terrifying rules, and helped her start a band. He also read the entire Bible in ONE NIGHT so he could go to prom with her — name another Gilmore boyfriend who worked that hard.
I’ll wait.
13. Paris Geller
Paris Geller (Liza Weil) is the real engine of Gilmore Girls. Yes, she did in fact start off as a bully, but the equal parts academic weapon and tiny dictator was simply an icon in my eyes as she clawed and ranted her way into being the most watchable character on the show. From having the most realistic night time fit check, to being able to clock Rory when the rest of us were yelling at the screen she is my diva for real.
12. Lane Kim
Keiko Agena’s Lane never got the story arc she deserved, but she’ll always rank high for hiding contraband CDs under floorboards, drumming for Hep Alien, and somehow tolerating Rory ditching her again and again.
She deserved stadium tours. She got twins and Zack (Todd Lowe). Tragic.
11. Richard Gilmore
The late Edward Herrmann brought a gravitas the show desperately needed. Richard was equal parts intimidating WASP patriarch and soft grandpa with a penchant for overlong toasts. When Herrmann passed in 2014, the cast — and fandom — were gutted, proof of just how central he was to the heart of the show.
10. Luke Danes
Without Luke (Scott Patterson), Stars Hollow falls apart. The man supplied caffeine, tough love, and a tolerance for the world’s most annoying town troubadour.
He was definitely the comfort character of the series — but let’s not forget, this is the man who couldn’t confess his feelings for four years. Sir, please.
9. Michel Gérard
Dragonfly Inn’s concierge was so funny he didn’t even need a side plot. Yanic Truesdale played Michel with pure disdain — for guests, for children, for cardio that wasn’t on a treadmill. The man was an inspiration in setting workplace boundaries.
I have long said he deserved way more screen time, and yep, I’d watch an entire spinoff of Michel versus basic humanity.
8. Sookie St James
Melissa McCarthy’s Sookie was chaos plus sugar plus knives. Half the time she was burning her hand off or spilling things (I felt seen), the other half she was the kindest, most supportive mess a friend could have.
Sookie does lose points for being what seemed like the worst boss to ever work for and not putting in any effort when the inn that both Lorelai and her owned was being built. Notably, when Lorelei had to run out of a hair appointment because Sookie didn’t show up to approve a stove that no one else could’ve approved. Like???
Love her bandanas though!!
7. Emily Gilmore
You’d think that she’d be closer to the worsts on the list but there will never be another Emily Gilmore (Kelly Bishop). Emily wasn’t cruel, she just absolutely refused to lower her standards.
She demolished social enemies at luncheons, terrorised staff with terrifying efficiency, and somehow became the most quotable Gilmore of them all.
Her downfall comes from her stubbornness and also for causing a breakup between Lorelai and Luke and then also lowkey between Rory and Dean.
And yes, did she essentially bribe her daughter to spend time with her? Yes! But, it was out of love!!! Sorry she’s a good negotiator.
6. Jess Mariano
Milo Ventimiglia’s Jess was hot, moody, and allergic to communication. He read more than anyone else on the show, but being horny for Kerouac doesn’t excuse being a brat to literally everyone. YEAH THAT’S RIGHT I SAID IT.
Still, he matured by the Netflix revival, which honestly was a rare win for the Gilmore men. Points for growth, but not enough.
5. Logan Huntzberger
Logan (Matt Czuchry) was Rory’s rich-boy phase: martinis and private jets and pretending journalism is something you can buy. Funnily enough, he was my favourite of Rory’s boyfriends for most of my life, until I went to therapy and learned not to settle.
He was never evil, but he was also never as compelling as the show wanted him to be. He had one good storyline later on — that’s about it.
4. Dean Forester
Dean started out fine — Jared Padalecki doing his very best “sensitive tall boy” routine — but quickly slid into clinginess and public meltdowns.
Breaking up with Rory at her job? At Doose’s Market?? Unacceptable.
Not being supportive of Rory’s dreams of getting into Harvard? Unacceptable.
Cheating on your literal wife Lindsay (Arielle Kebbel)???? UNACCEPTABLE.
His saving grace is that my friends and I have come up with a drinking game where we take a shot every time he chucks a tantrum and that has proven quite fun. So, thanks, I guess.
3. Christopher Hayden
Christopher (David Sutcliffe) was permanence’s evil twin. He’d swoop back into Lorelai’s life, bring promises and bad timing, then bail as fast as he arrived.
A man with endless potential, squandered even faster than Rory’s integrity.
2. Lorelai Gilmore
Yes, the girlboss of Stars Hollow was funny and fun and charming. But Lorelai was also selfish, emotionally sloppy, and maybe the biggest reason Luke grew that constant frown line.
The girly ran away from her wedding to sweet Max Madena, was a diabolical daughter calling Pennilyn Lott her “almost-mummy”, and was rude at other people’s major life events (the baptism, Fran’s funeral, Richard’s funeral).
Not to mention she kept a grudge against her parents well into her thirties and forties about something that happened when she was a child. Granted, it was a whole child coming out of her, but still!
1. Rory Gilmore
And here we are: the fall of a once-great protagonist. Rory went from bookish Yale aspirant to cheating on Dean, stringing along Jess, and bailing on Lane’s gigs for boy drama.
At best, she was entitled.
At worst, she was the villain of her own show and I have the receipts:
- Rory missed Lorelai’s graduation.
- She constantly was ditching Lane for the boys in her life.
- Rory kissed Jess and then straight up ghosted him.
- She never wanted to admit that she was a nepo baby.
- Rory slept with Dean while he was married and then had the audacity to call him “my Dean”.
- She stole a whole ass yacht and then dropped out of Yale?? LIKE REGULATE YOUR EMOTIONS MISS MA’AM.
- There’s more but now I need to regulate my emotions.
Although, I do hate on her, Rory Gilmore was still my problematic icon growing up and I am still determined to get through her reading list. Also, she was a fictional character and I need to calm down.
So there you have it, Gilmore Girls is 25, and the love–hate’s still real. Some characters got better with age (Paris, Richard). Some just got worse (Dean, Rory). And some — Dave bloody Rygalski — remain perfect angels taken from us far too soon.
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