Actress: Rachael Leigh Cook
Film: She's All That (1999)

The very popular 1999 retelling of George Bernard Shaw's Pygmalion (see also 1964's My Fair Lady) is not exactly high art, but the one character who is supposed to carry that sense of the artist's suffering for meaning is none other than Laney Boggs. Living without a mother has created a life of very few pleasures. Working behind the counter at a local food joint and taking care of her brother and incompetent father really focus her remaining energy on her true passion, painting. Only she's terrible. All the paint covered overalls in the world won't hide that fact that she's not hasn't advanced much since elementary school.