How many David Fincher videos made the cut?
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Madonna's imagery is taken from concert footage, but the animated landscape is perfect for the rhythm of the song and its more beautiful than it has any right to be.
Drowned World/Substitute for Love
It might have come a bit too soon after Princess Diana's tragic death, but this chronicling of Madonna's second guessing at fame is one of her most personal songs and videos ever. You might even feel sorry for her. Maybe.
The S&M imagery was a little tame after "Justify My Love," but it likely the most successful and subtle integration of modern dance into a pop music video ever.
Want to talk about iconic imagery? How about the metallic-look Madonna endures for this club classic?
Fincher's last collaboration with Madonna is highly polished and moving, but it can't save a dud of a song.
Papa Don't Preach
Would have been no. 11 on this list. The first video that showed - rightly or wrongly - that Madonna could be a successful actress. Cinematically, it still holds up over 25 years since its debut.