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Slide 5 of 9

Jess: The Wheel of Fortune

This motherf*cker. I am 100 percent Team Jess, but I can see his faults just like anyone else. Jess embodied the exciting nature of change in the Gilmore world: Nothing is for certain! I'm here for you! No, I'm not! I'm staying in Stars Hollow! No, I'm going to California! I'm not finishing high school! Wait, I wrote a book! Jess's unpredictable nature makes him sexy and alluring, even though we all knew Rory couldn't count on him. Lane said it best: "Every girl has to fall for a bad boy. It's the rule. It's the reason so many accountants eventually get married."

Image Source: Everett Collection