Year: 1989
Director: David Fincher
Why: The second of Fincher's four collaborations with Madonna, "Oh Father" is a gorgeously storyboarded black and white production where no frame is wasted. Madonna is quoted as saying the semi-autobiographical video was her attempt to make peace with her mother's death. Whether that is truly the case is unclear, but Fincher creates some incredibly powerful images to tell the story with recurring motifs of snow and moving shadows. One scene featuring Madonna, her father (now an old man), the shadows of her younger self and her younger father is striking in how it conveys so much pain in just a few moments of screen time.  The shot not only shows Madonna's angst in the present, but her pain in the past in one quick tracking shot. Like much of the imagery in the video, it's remarkable.

Watch it here.