All 14 major Gilmore Girls characters ranked from worst to best

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Dean in Gilmore Girls

14. Jason “Digger “Stiles

The main reason Digger ranks as the “worst” character in Gilmore Girls has to do with the fact that he was largely inconsequential in the grand scope of the series. Chris Eigeman appeared in only one season (the fourth) as the rich boyfriend of Lorelai and short-lived business parter of her father, Richard. If you zoom out on the series, he’s but a blip on the timeline, quickly forgotten following his and Lorelai’s breakup… and that’s fine.

Digger wasn’t bad by any means, but I don’t think he’s in contention for anyone’s favorite Gilmore Girls character. While endearing and good to Lorelai, he was also the complete antithesis of her other serious relationships with Luke and Christopher (and those two are already polar opposites, so what does that tell you?). Truly he didn’t have much longevity in the show, and it’s a wonder he was added to the main cast over some of the more worthy Stars Hollow citizens.

13. Dean Forrester

Dean catches a lot of smoke from Gilmore Girls fans, but that’s not going to stop here. Obviously, Jared Padalecki is great, but Dean… He’s not as great of a boyfriend as the first two seasons would lead us to believe. Yes, he’s a wonderful first boyfriend for Rory. He treats her very well and makes her feel loved. But he was also selfish and jealous to an annoying extent. Remember the episode where he left message upon message on the answering machine? It’s not a cancellable offense, but it’s still evidence of Dean being difficult to cheer on and really like.

12. Logan Huntzberger

Perhaps a flipped version of Dean, Rory’s college boyfriend Logan was easy to love because of his charm (and that smile!), but he didn’t always treat our girl in a way that she deserved. Personally, and I know I’m making this list, Logan might be ranked a little too close to the “worst” end of the spectrum, and maybe if A Year in the Life hadn’t happened, he’d have managed to make it more toward the middle. As a long-time Logan defender, I still can’t ignore some of his choices.

First things first, Matt Czuchry is amazing in the role, and no one could have stepped into the very specific tone of this character (something that could be said about most of the characters). But Logan is reckless. That’s fun and exciting, necessary even, for Rory in the beginning, though quickly turns destructive and troubling. In the revival miniseries, Logan cheats on his fiancée with Rory, which presumably results in a pregnancy. Where Logan leads, chaos follows!