Gilmore Girls centers itself around the relationship between Lorelai and Rory Gilmore but the people in and out of their lives have just as many fans. Gilmore Girls isn't the kind of show where the bad guys are chasing the good guys and viewers are hoping the likes of the Gilmores pull through.
Instead, the villains are dressed as people viewers thought they could trust. These are villainous characters who don't even realize that they can, at times, be the villain. Viewers know that Emily Gilmore, Paris (in her earlier days at Chilton), and Mitchum Huntzberger were villains in their own right. But they're not the only ones. Stars Hollow is full of people with bad tendencies who don't even realizing it.
Rory Gilmore
Diehard fans who have watched the series over and over again know that Rory is sometimes her own worst enemy, and a villain who plays dumb. Due to Rory's upbringing where she was told how wonderful she was on a daily basis, she was ill-prepared for the real world. She ruined a stranger's downtime when he sat under "her" tree at Yale, she brought down Dean's marriage because he was "her Dean," and she stole a yacht thinking that her wealthy grandparents would be able to smooth things over. Rory drags a pile of broken hearts behind her and doesn't realize why. As Marty once said, Rory can be annoying due to her nativity.
Lorelai Gilmore
Similar to Rory, Lorelai is also naive to the fact that she bosses people around and does things without ever thinking about the repercussions. With many of Lorelai's storylines focusing on her personal life, she was the villain in most relationships.
She led Max on and dumped him before their wedding without a reason, she steamrolled Luke into getting what she wanted (because she knew he was too soft for her to say no), and she practically blamed everything on her upbringing when things went wrong. As strong and responsible as Lorelai is, her selfishness made her a villain.
Christopher Hayden
Christopher wanted to be the good guy in this story but he wasn't. He always thought that because he was Rory's dad and Lorelai's first love that he'd have an easy time nudging his way into their lives whenever he wanted to but it never ended that way. Christopher always made a mess of his relationship with Lorelai (especially when Sherry got pregnant) and he was an absent father who didn't really know his daughter. Christopher tried to be the good guy but too much has happened for that to be true. Even Stars Hollow wasn't a fan of Christopher, and that's saying something.
Dean Forester
The relationship between Rory and Dean is romanticized because they were each other's first loves. They were both so young when they started dating and they remained friends when it didn't work out. Because of their inexperience and youth, Dean came off as controlling and pushy in his relationship with Rory.
It got to a point where Rory didn't want to hang out or talk to him as much because she couldn't be herself. Dean became the villain in his own life when he cheated on his wife with his ex-girlfriend and didn't come clean about it.
Heaster Charleston
Heaster of Chilton, Charleston was a very stoic and professional character in Gilmore Girls; he even came back for the Netflix reboot. And while Heaster Charleston was good at his job, he was also seen as the villain in some of his students' eyes.
In the earlier seasons, Charleston told Rory that her desire to be alone made her look like an unapproachable loner and that she had to change her personality if she wanted to get into an Ivy League school. He also told Lorelai that she didn't do enough for Rory or the school (regardless of the fact that she was a busy single mom), and he even strongarmed Rory to host a Chilton student when she was at Yale. As poised as he was, Charleston had his villainous moments.
Taylor Doose
As the town selectman, Taylor was Stars Hollow's biggest cheerleader and villain. His need to make Stars Hollow great came at the expense of the locals. He made plenty of changes without running it by people or ignoring their responses to said changes. Taylor was sweet deep down but his need for power and control made him the ultimate Stars Hollow bad guy.
Zack Van Gerbig
Not many Gilmore Girls fans were thrilled with Lane and Zack's relationship. Sure, they had the band in common but that was pretty much it. After seeing Lane so happy with Dave, Zack was an upsetting follow-up boyfriend.
His personality came off as mediocre and unintelligent. He was also quite controlling and whiny when things didn't go his way. Zack was a man-child who wasn't ready to grow up. He was the villain in Lane's life without realizing it.
Mrs. Kim
The sad thing about Mrs. Kim is that she didn't mean to be the villain but she absolutely was a negative force in Lane Kim's life. Mrs. Kim devoted herself to her family traditions and religion; two respectable and understandable devotions. What she failed to do, however, was see how her personal views affected her daughter. Lane never felt herself when she was around her mom and she was afraid of mes as so not to embarrass her. Lane was deeply scarred by her childhood and it affected her in her adult life.
Anna Nardini
Everyone was shocked when Luke had a child, April, that he had no idea about. Anna Nardini didn't feel comfortable telling Luke about her pregnancy because he didn't seem like a kids' guy. She figured it would have been easier raising April alone instead.
When Luke found out about April, Anna was understanding of Luke's desire to help out and welcomed it, but as soon as April and Luke became too close, Anna became the villain. She started taking April from him, she stopped being communicative, and she even moved without running it by Luke! Anna could have been great but she was anything but.
Sherry Tinsdale
Like many of these characters, Sherry also seemed loving and sweet but she turned into the villain who couldn't handle her own life. She tried forcing a relationship with Rory, which was irable at first but not honest. Sherry also turned Christopher into the man she wanted instead of accepting him for who he was. Once she had their daughter Gigi, Sherry left the scene entirely. She couldn't handle being a fiancée and a mother and fled for Europe, leaving Christopher as a single dad. It was gutless.