13. "Oh Father" (1989)
You have to respect a video that opens with a nod to Citizen Kane and gets more ambitious from there. Working for the second time with director David Fincher, Madonna dug deep for this mini-epic about her mother's death, her troubled relationship with her father and her tempestuous marriage to Sean Penn. "It's my most autobiographical work — with a little bit of drama thrown in," she would tell Cosmopolitan, adding, "It's boring to be completely autobiographical." "Oh Father" offers some of the most evocative and disturbing images in all of Madonna's oeuvre, among them the sight of a young girl stepping up to her mother's coffin to find that the dead woman's lips have been sewn shut — which reportedly came from the singer's memories of her own mother's funeral.
The song and the video were very personal for Madonna, but, interestingly, it didn't appear to be her idea to release it as a single. "I had kinda talked Madonna into releasing 'Oh Father' as a single and we did this video and we were very happy with the video and nobody ever saw it because the song wasn't a hit," Fincher told The Guardian, "so she came back to me and said, 'You screwed me up. You wanted to make this video for the song and no one liked the song and I went to bat for you and now I have to make a video by Tuesday.' And I said, 'What's the song called?' And she said, 'Vogue.'"