5. Josie Geller (Drew Barrymore) in 'Never Been Kissed' (1999)

Poor Josie with her horrible side-ponytail and dental headgear is the butt of every joke at her school and gets egged by her supposed date on prom night. Years later, she gets her chance to finally come back in style and be popular as part of an undercover journalism assignment, leading to the triumphant geek-girl cry, "I'm not Josie Grossie anymore!"