Jess Mariano (Milo Ventimiglia) was the Gilmore Girls version of the notorious bad boy: dark looks, surly attitude, the-world-can-bite-me outlook, and sarcastic charm. He was Rory’s (Alexis Bledel) second boyfriend, and the only boyfriend that shared many of the same interests as she did – most importantly, their love of books. When he first came to town to live with his Uncle Luke (Scott Patterson), the Stars Hollow residents immediately detested the outsider, especially when he went out with Rory. Yet, as the seasons passed, Jess grew up and really made something of himself. Along the way, however, he’s made memorable remarks that reflect his personality (and remind us why we love Jess). Here are ten of Jess’s best quotes!
10 I think I hung my Tool T-Shirt…
You know, I think I hung my Tool T-Shirt next to my Metallica T-Shirt and they don’t really get along.
Jess’s arrival in Season 2 started off with a bang. He was somewhat pensive and had an angry vibe. When he mentions his T-shirt fiasco, it’s to avoid talking to his mother. It’s clear Jess has a complicated family life and resents being sent to Stars Hollow, but this humorous excuse is memorable as part of the introduction to Jess’s personality and sarcastic out-of-the-box thinking when it comes to excuses. In any case, it’s clear Jess is the typical bad boy from the attitude to the cigarettes to the way he loathes Stars Hollow – until he meets Rory.
9 Basket. Basket-maker…
Basket. Basket-maker. Guy who didn’t bring enough money.
Jess and Dean’s (Jared Padalecki) rivalry was the love triangle of Gilmore Girls. In “A-Tisket, A-Tasket”, Jess outbids Dean for Rory’s picnic basket, and by Stars Hollow tradition, earns Rory’s basket and her company in exchange. Dean, furious, pleads with Rory not to go but she does anyway.
In this episode we see Jess is ready to battle Dean for Rory’s affections, and succeeds in connecting with her, the episode ending with Rory calling Jess and the two falling into easy conversation. If anything, this was the episode that launched the will-they or won’t-they chemistry between Jess and Rory. Mission accomplished, Jess.
8 It’s a crazy world we live in.
Jess has the ability to capture what we feel in certain moments in a succinct manner. While this was his response to Rory who was upset at the idea of being the poster girl for censorship at Stars Hollow’s version of a Blockbuster, it can be applied to just about anything in our lives. From what’s acceptable to the outraged feelings we get while stuck in traffic or when our favorite restaurant is out of our favorite dish for the day. Whatever the reason, we fall back to Jess’s simple “it’s a crazy world we live in.”
7 Think how dull your life would be without me.
Jess was right. Gilmore Girls, let alone Rory’s life, would have been dull without Jess. Jess added a new energy to the show, and an element of danger and mystery to Rory’s life, opening her eyes to new experiences and ideas both good and bad.
Jess changed Rory’s life and is part of the reason Rory became who she is. If Jess had never existed, Rory never would have done things like skipping school or dating someone her mother didn’t approve of. Then again, if not for Jess, she never would’ve gone back to Yale and fulfilled her dreams, either.
6 I’m sorry. I thought this was the uniform.
Who could forget Jess making fun of Luke with the flannel shirt and backwards hat combo? When Luke admonishes Jess’s choice of attire (a graphic Metallica shirt), Jess later makes a point of making fun of his uncle, much to our amusement. This happened at the beginning of Jess and Luke getting to know one another, showing us a fun, sarcastic kind of relationship between the two that eventually grows into a meaningful bond over the course of the series. It’s rare that we ever see Luke without flannel or a backwards hat, so Jess probably does have a point.
5 I don’t want to talk to anybody else…
I don’t want to talk to anybody else. I don’t like anybody else.
Jess totally gets us all with this quote. We’ve all been in that situation where you’re at a party or some other kind of social gathering, and you don’t feel like mingling, so you stick to your person or small group.
Jess was having a bad night in this particular episode, but this quote was actually quite thoughtful. After all, he’s telling Rory how much she means to him (in his own way, of course). For us viewers, we know how that night goes down. Nonetheless, this quote is honest. And we’ll probably use it at some point in our lives to escape awkward or downright painful situations.
4 I love you.
All fans remember the moment. Jess is back in town; he chases Rory down to tell her one thing: he loves her. The sad truth is, it’s too late. Even worse? Jess drives away before a shocked-into-silence Rory can respond. While the two have a complicated history and remained friends, it’s clear the feelings still exist. Should there be another Gilmore Girls revival, maybe Jess and Rory could end up together. You never know. It always seemed like something there was unfinished.
3 I was just walking by…
I was just walking by and the thing came out of nowhere and bam! Beaked me right in the eye.
No one had heard “beaked” as a verb until Jess described the unfortunate source of his black eye. The black eye is blown completely out of proportion when Rory believes Jess got into a fight with Dean, which results in a fight between her and Jess instead.
They make up, but the funny thing is Jess only tells Luke the real reason why he’s sporting a black eye, too embarrassed to tell Rory or anyone else. This is also one of Jess’s funniest moments; he may be rebellious and cool, but even he’s not immune to violent run-ins with a swan.
2 I want to be good…
I want to be good. Life’s just not letting me.
This could probably be Jess’s life motto, even if he was saying it sarcastically. It’s no secret Jess came from a troubled family background and experienced anger and resentment to varying degrees, resulting in his bad boy tendencies and teenage rebellion. Jess allowed his experiences and background to hold him back; that is, until Rory pushed him and convinced him that he could do and become more. Thankfully Jess took the advice and encouragement; he outgrew his setbacks and showed life that he could be good without its permission.
1 You should write a book.
Okay, this might not be one of Jess’s most memorable quotes, but it’s certainly one of the most meaningful. He’s always there for Rory when she needs him the most. She’s lost and dropped out of Yale? Jess convinces her to go back and fulfill her dreams. In the revival, Rory’s landed in a rut and doesn’t know what to do next. It’s Jess who gives her the idea to write a book about her life with her mother. Jess turns out to be pretty good at giving advice, and even better at getting Rory back on track when she’s gone off her path. In a way, Jess is a navigator, guiding Rory at different times in her life.
Jess is certainly one of our favorite characters. From his quotes to his antics (remember the outline he drew of the fake dead body as a prank?), Jess certainly left his mark in the Gilmore Girls universe in both the original and the revival. So yeah, he was defiant and rebellious, but also sincere and profound in his own way. He grew up a lot over the course of the series, learning the hard way but turning his mistakes around and creating a life and various successes for himself. Though of course, he hasn’t lost his sarcasm, wit or bad boy charm.
NEXT: Guest Stars On Gilmore Girls, Ranked