Rory: The Fool
Rory starts her journey as this cherub-faced innocent, a "Mary" wandering the halls of Chilton with equal parts naiveté and enthusiasm for her lifelong goal of becoming Christiane Amanpour. Through trials and tribulations, and lots of screw ups and wins, she ends the (original) series a smartly dressed Pantene model — those bangs! — ready to hit the campaign trail with Senator Barack Obama. She had her fanny pack and her tiny, tiny sweaters, and she was ready to take on the world, having somehow found the chutzpah to even turn down the right-on-schedule yet publicly humiliating marriage proposal of Heir Huntzberger.