7. Clueless (1995)
I'm secure enough in my masculinity to admit that I liked Clueless a lot, and admit it fellas, you did too. However, when I really think about the fundamentals of this movie, it shouldn't be good. It's about a superficial, spoiled Valley Girl who genuinely believes that looks and popularity are everything--who wants to see that? However, when one actually watches the movie it wins you over with its humor, characters, and story of 15-year-old Cher. While Cher is kind of a brat, she does care about other people, and actually wants to see people happier--even if her idea of happiness is a little skewed.