12. Girl Gone Wild (Mert Alas and Marcus Piggott, 2012)
A real throwback to her earlier days, this does what a good Madonna video should; have great dancing, good wigs and hot, shirtless men. Shot in black and white and featuring vogueing, homoeroticism and men in high heels, this is classic Madonna. It’s also a super dance track.
11. What It Feels Like For a Girl (Guy Ritchie, 2000)
Madonna’s second video banned from the airwaves features her and an elderly woman (from the ‘Ol Kuntz’ rest home, no less) tearing around town in a Trans-Am, robbing people, fucking with the cops and causing general melee. The video was banned for being too violent but even for 2000 this was a pretty flimsy case, especially in comparison with so many videos allowed to air at the time. I don’t think a lot of people understood the irony of that; of what the song and video represented about the double standards and misogyny that exist for women. The controversy didn’t result in the song being a very big hit but Madonna, but she repeated the success from her ‘Justify My Love’ days and released the video on DVD, which became the best-selling DVD single of 2001.
10. Bedtime Story (Mark Romanek, 1995) and Nothing Really Matters (Johan Renck, 1999)
Yeah, so I’m cheating a bit having two together but this pair of truly avant-garde videos are great examples of Madonna going off book and subverting expectations and succeeding enormously in the process. ‘Bedtime Story’ is a spectacular surrealist dream, unlike anything she had attempted in her career to this point and completely befitting such an esoterically song as written by Bjork. Replete with whirling dervishes and the singer giving ‘birth’ to a flock of doves and, of course, half a dozen glorious costume changes, ‘Bedtime Story’ remains one of her bravest works. ‘Nothing Really Matters’ exists deep in Japanese culture, with Madonna contorting and convulsing like an epileptic geisha in a crimson kimono (in a good way though) with extras that look like they’re from The Ring (again, in a good way). Johan Renck’s direction of the video was creative and brilliant, even if the single and video weren’t that successful commercially.
9. Drowned World/Substitute for Love (Walter Stern, 1998)
Deeply personal themes of motherhood and fame permeate this song and video, which features Madonna being chased through the streets by paparazzi on motorcycles, very eerily echoing the demise of Princess Diana under the same circumstances just a few months before. It’s a risky and brave concept that pays off. It also features one of the best endings to a Madonna video ever, all Mama Bear realness and protecting her own.