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.
7. Human Nature (Jean-Baptiste Mondino, 1995)
There’s nothing quite like a Madonna scorned. Burned and bruised from the bashing she took for her ‘Sex’ book and the sexuality of her Erotica album, Madonna fought back at her critics in a stinging song (“I’m not your bitch, don’t hang your shit on me”) and a video from her ‘Justify My Love’ director Jean-Baptiste Mondino that features Madonna and her dancers in second-skin rubber outfits writhing and intertwined with each other in an in-your-face response to “oops, I didn’t know I couldn’t take about sex” mentality. Its striking, hyperreal photography is fabulous. As are the costumes, wigs and dancing.
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.