30. Mitchum Huntzberger (Gregg Henry)
If you didn't hate Mitchum before you even met him, you need to re-watch Gilmore Girls. The evil father of Rory's (Alexis Bledel) college boyfriend, Logan Huntzberger (Matt Czuchry), told her she wasn't going to make it as a journalist, starting a ripple effect that would lead to her getting arrested for stealing a boat, dropping out of college, moving in with her grandparents, and not speaking to her mother (Lauren Graham) for months. And then, he had the audacity to take credit for her success the following year when she became editor in chief of the Yale Daily News. Your gut sucks, Mitchum!
29. Rune (Max Perlich)
Rune was the epitome of the date from hell. Jackson's (Jackson Douglas) cousin, who was squatting on Jackson's couch after losing his job, agreed to go on a double date with Lorelai and Jackson and Sookie (Melissa McCarthy), kicking and screaming the entire time. He took issue with Lorelai before she could even fully open the door to greet him. And he not-so-discreetly complained to Jackson about Lorelai's height from two feet away on the porch. But revenge came to him every day in the form of having to tell people his name was Ruin...errr, I mean, Rune.
28. Tristan DuGrey (Chad Michael Murray)
Tristan picked on Rory more than anyone else at Chilton — with the exception of Paris (Liza Weil). He started calling her "Mary" on their first day because he thought she looked like the Virgin Mary. Even when Rory screamed at him to stop in the midst of a breakdown after being hit by a deer, he didn't drop the nickname. In a rare moment at a Chilton party, Tristan showed Rory a softer side. But the notorious bad boy still got himself shipped off to military school.*
*North Carolina, where he played Lucas on One Tree Hill.
27. Jason "Digger" Stiles (Chris Eigeman)
The son of Richard Gilmore's (Edward Herrmann) business partner and a co-camper of Lorelai's, Digger secretly left his father's company after Richard was ousted to start a new one. Digger was into secrets, sneaking around with Lorelai for weeks until a private investigator exposed their relationship to their parents. He wanted Lorelai to pick him over her family after Richard backstabbed him, and when she wouldn't, he left. He also made Emily Gilmore (Kelly Bishop) feel bad when he wanted to take clients to Atlantic City rather than have a cocktail party at the Gilmore home. Rude!
26. Taylor Doose (Michael Winters)
Yes, let's give Taylor some credit for holding the best city hall meetings in television history. But he was always butting heads with Luke (Scott Patterson) and gave Lorelai and Sookie a hard time with permits when they were trying to build The Dragonfly. He also let his "power" get the best of him and enacted some interesting efforts in Stars Hallow. Remember the stoplight? That really pissed off a lot of people.
25. Christopher Hayden (David Sutcliffe)
Yes, he creates excellent offspring, but Christopher is bad news. He's only a good father when he rolls through town twice a year and is always going after Lorelai when she's finally happy with someone else. He even teamed up with Emily Gilmore to break up Lorelai and Luke! And he should never, ever be forgiven for saying he wanted to start over with Lorelai at Sookie's wedding and then leaving her for his pregnant girlfriend the next day. (OK, he didn't want to abandon another child, but Rory needed a dad too!)
24. Brad Langford (Adam Wylie)
Poor Brad couldn't escape Paris' terror even after switching schools, when he was forced to come face to face with her at a debate tournament. While Brad didn't do much to deserve such torture, he didn't do much to help his situation either, besides taking a hiatus from school to be on Broadway and transferring. All right, maybe he did a few things, but it wasn't difficult to see how he could so easily annoy Paris.
23. Tom (Biff Yeager)
Tom is so high on this list mainly because he just didn't have that much screen time over the show's run. However, he deserves a lot of credit for making the Dragonfly Inn so wonderful and for secretly overseeing T.J.'s (Michael DeLuise) attempts to be a contractor at Lorelai's house.
22. Jamie (Brandon Barash)
Jamie was Paris' first boyfriend and was quite charming. He took her to his family cottage and everything! But then Paris had sex with him and got rejected from Harvard in the same week, and had a complete breakdown on C-Span. So one must wonder if he's to blame for her embarrassment just a tad?
21. Colin McCrae (Alan Loayza)
Colin should really be tied with Finn (Tanc Sade), but Colin's placed a tad higher because he brought a nice Dutch milkmaid back from the Netherlands and then basically abandoned her...
20. Finn (Tanc Sade)
But both Colin and Finn are at fault for encouraging Logan to go on crazy adventures, trying to pass for a gay couple to get information about Logan after his accident, and embarrassing Rory in the middle of a lecture hall.
19. T.J. (Michael DeLuise)
T.J. makes Liz (Kathleen Wilhoite) really happy. And that makes Liz's brother Luke really happy. So T.J. gets a thumbs up. Though he is constantly making a mess of things (usually literally — he's trying to be a contractor, after all), he always means well. And any man that can wear tights for his bride is a keeper.
18. Morey Dell (Ted Rooney)
Like Tom, Morey also doesn't have that much screen time throughout the series. But Lorelai and Rory's neighbor is so beloved. He's got that cool, calm, and collected look, voice, and vibe. And he lives in a house that is too short for him. But he does it all for his love, Babette (Sally Struthers). We should all be so lucky.
17. Gil (Sebastian Bach)
Gil really was the brains behind "Hep Alien." He brought a new sound to the group — and great sandwiches from his day job! He's a keeper.
16. Glenn Babble (Ethan Cohn)
15. Henry Cho (Eddie Shin)
Henry, a classmate of Rory's, was so sweet to Lane (Keiko Agena). He met Lane when Rory dragged her to a Chilton party and after he danced with Lane, he tracked her because he couldn't let her go. He even kept calling her house (but hanging up because her mom answered)! And he worked with Rory to secretly chat with Lane because he was THAT nice. He had a little trouble with trigonometry, but hey, who doesn't?
14. Brian Fuller (John Cabrera)
Brian was so nice! He was a great roommate, especially when he found out his other two roommates were dating. And he went above and beyond to help Lane and Zack (Todd Lowe) with their twin babies.
13. Doyle McMaster (Danny Strong)
Doyle really came from behind to develop into a fan favorite. At first, he was an annoying and somewhat rude editor, but Doyle turned into an annoying and somewhat rude friend of Rory's. While he didn't really change, he became more endearing once he started dating Paris and they could crack unfunny jokes together about each of them sleeping with the Yale Daily News editor and practicing yoga. He also was kind to Rory when she felt, once again, defeated by Logan, and they sweetly drank away their sorrows together.
12. Richard Gilmore (Edward Herrmann)
Richard cares so much for the women in his life. He agrees to loan Lorelai money for Rory's Chilton tuition, no questions asked. He is immensely proud of Rory, constantly bragging about her (and trying to name a building at Yale after her). And he loves Emily, even through the rough patches in their marriage, and gives her whatever she wants. Plus, he is so adorably old school with his sweater vests and martinis.
11. Dave Rygalski (Adam Brody)
Any boy that will read the ENTIRE Bible cover-to-cover in one night is a keeper...in Lane's eyes, at least. Dave was adorable, inside and out. And his move to California broke everyone's hearts, even Mrs. Kim's (Emily Kuroda).
10. Kirk Gleason (Sean Gunn)
Kirk was the quirkiest person in Stars Hallow, maybe in America, but he was unapologetically true to himself and that's what makes him so lovable. Even when he was stepping into his fifteenth job that season, he was beyond confident. I mean, remember when he used pictures from WWII to show Lorelai and Max (Scott Cohen) he could be a photographer? Even his night terrors that forced him to run around naked (since he slept in the nude) couldn't hold him back. Also, he and Lulu (Rini Bell) made an adorable couple.
9. Logan Huntzberger (Matt Czuchry)
Yes, Logan ended up sucking as a boyfriend and person, but he was (mostly) really good to Rory. He helped her get an inside look at a secret society on campus. When she wanted to stop fooling around with him, he immediately said he wanted to be her boyfriend. And while he can and should be blamed for blowing Rory off and getting back into bad habits, he was right there for her during her fight with Lorelai. He truly cared for Rory and it's hard to blame him for walking away from her all together after she turned down his proposal. After all, his heart was crushed.
8. Dean Forester (Jared Padalecki)
Ah, the good boy. Everyone loved Dean. He was kind and simple and only got mad at Rory when she didn't have enough time to spend with him. HE MADE HER A CAR, FOR GOODNESS SAKE. But the way Dean cheated on Lindsay (Arielle Kebbel) with Rory and his attempts to hold onto her while she was at Yale were unflattering and unfair. Yes, Dean was great, but only for so long.
7. Marty (Wayne Wilcox)
Marty was the most underappreciated of all the men Rory was involved with. He would sit with her and watch old movies and eat junk food forever on that couch if that's what she wanted. And when he finally built up the courage to tell Rory he liked her, she responded by saying she liked Logan, a guy who, by the way, was a total jerk to Marty. It was weird years later when Marty lied about ever knowing Rory, but everyone has their faults. And she did break his heart, after all.
6. Zack Van Gerbig (Todd Lowe)
Zack and Lane were the perfect couple. He was so respectful of Lane and her mother! He was easygoing and always tried his best, and though he didn't have a great job, he would try to do little things for Lane when he could, like buying her brand name paper towel. That is true love.
5. Max Medina (Scott Cohen)
I love you, Luke (Scott Patterson), but, in the words of Rory Gilmore, I really wish Max would have been Rory's stepfather. Max cared so much for Lorelai and Rory and did anything to make them happy. And if that meant being the furthest away, but still getting up to answer the phone, he would do it. If it meant moving far from his job to live with Lorelai in the home she loved, he would do it. His only hiccup in this relationship was jumping into an engagement. But, even still, Lorelai didn't treat him fairly.
4. Jackson Belleville (Jackson Douglas)
Sookie and Jackson were really the best couple on Gilmore Girls. Jackson was the sweetest guy you'd ever meet. I mean, who would sleep in the backyard with his crops to protect them from the elements, or figure out a way to get rid of many tons of marijuana that were accidentally planted in his backyard? He was the best worker, husband, father, and friend. And Jackson, and his outfits, will always have a special place in the hearts of all Gilmore Girls fans.
3. Michel Gerard (Yanic Truesdale)
2. Luke Danes (Scott Patterson)
Of course it was going to be Luke! Sorry, Christopher, but Luke was meant to be Rory's father. He fed her amazing food, let her study in his diner for hours, cheered her on at her college graduation, moved mattresses in and out and out and in of her dorm room, and threw the goodbye party of all goodbye parties. As for Lorelai, even when he was mad or annoyed with her, he was always doing things to make her happy. He stood on the side for years, and even when things between them were bad, he worked hard to get her back. It's comforting to know, with Rory probably still covering Barack Obama, that Lorelai and Luke are living a lovely quiet life together.
1. Jess Mariano (Milo Ventimiglia)
This may be a controversial pick, but Jess was the best. He's the sort of bad boy who rebels against everything he knows in his world, but secretly loves to enter others through books. And you just don't find guys like that any more. Though he stole the gnome, got into a car accident with Rory in the passenger seat, and left town without saying goodbye, Jess will always be the guy Rory should have been with in the end. He was Rory's Dodger and she couldn't fault him for that. And he always listened to Rory, following her advice and really pulling his life together, writing a novel, getting it published, and saving enough money to pay Luke back. In an ideal world, Rory and Jess would have pulled a Huckleberry Finn, bought a boat, and sailed away together. But we can still dream. Jess certainly did.