1. "Express Yourself" (1989)
Taking total control of the artistic process, Madonna worked with director David Fincher to make a sci-fi classic
The first of Madonna's collaborations with acclaimed Fight Club and Social Network director David Fincher is also her most ambitious use of the video form (and, at $5 million, the most expensive video ever made at the time). Heavily influenced by German director Fritz Lang's 1927 classic Metropolis, with its sci-fi cityscape and surreal factory scenes, "Express Yourself" is a perfect melding of Fincher's expressionist impulses and Madonna's shape-shifting allure. ("We sat down and threw out every idea we could," Madonna said.) She played different seductive characters: a pantsuit-wearing, Marlene Dietrich-like figure, a shimmying coquette in a corset, a submissive wife chained half naked to a bed. "This one I had the most amount of input," said Madonna. "I oversaw everything – the building of the sets, everyone's costumes, I had meetings with makeup and hair and the cinematographer, everybody. Casting, finding the right cat – just every aspect. Kind of like making a little movie."