8. Frozen (Chris Cunningham, 1998)
One of, if not the, darkest videos Madonna has made. Both visually and thematically. Levitating above a desert flat and erupting into a murder of crows, this video from Chris Cunningham gave Madonna one of her most striking ever to accompany one of her richest and most luxurious compositions.
6. Express Yourself (David Fincher, 1989)
It doesn’t get much more classic Madonna than this David Fincher-directed and Metropolis-inspired masterpiece that features the singer as the wife of the owner of an enormous factory populated by soaking wet, shirtless muscled men. See, classic Madonna. Dazzling photography and production values, to the tune of $5 million dollars (a record for a music video at the time) give the video a lush look and Madonna’s takeover of the company reinforces her commitment to gender-bending politics in her work.
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Burning up is one of my favorites. I also like Gambler (from the movie Vision Quest) and Music.