Drew Barrymore As Josie Gellar

Looking at Drew Barrymore, especially at the height of her ‘90s fame, the word gross would probably be the last thing on your mind. That’s what makes her portrayal of social outcast Josie ‘Grossie’ Gellar in Never Been Kissed all the more applause-worthy. What’s more, Barrymore actually had a much different childhood than the character.

While Josie grappled with bullying because of her looks, the Charlie’s Angels star dealt with addiction early in life. Fortunately, both of them got a happy ending. Josie finally got her romantic kiss, and Barrymore got her life back on track and now hosts The Drew Barrymore Show.