10. 'Papa Don't Preach'
Madonna debuted a rather unglamorous, tomboy look for her 1986 "Papa Don't Preach" video. It fit nicely with the song's serious subject matter: a pregnant young woman confronting her father. Many in the pro-life movement saw the song as a new anthem because Madonna repeatedly states her intention to keep her baby.
"There were so many opinions," she told Rolling Stone in 2009. "That's why I thought it was so great. Is she for 'schma-smortion,' as they say in Knocked Up? Is she against abortion?" Madonna never quite gave an answer, though she did explain why the song appealed to her. "It just fit right in with my own personal zeitgeist of standing up to male authorities," she said, "whether it's the pope or the Catholic Church or my father and his conservative, patriarchal ways."