5. Vogue (David Fincher, 1990)
Despite being at #5 on my list, ‘Vogue’ is probably her most respected video that ends up as #1 on most lists of her best videos. And deservedly so, it’s pretty much perfect. Another David Fincher collaboration, this stunning black and white creation features Madonna and her Truth or Dare dancers vogueing their way through a minimalist set that evokes the 1920s and 1930s while she name-drops leading men and starlets of Hollywood’s Golden Age. The introduction of vogueing to mainstream from its Harlem drag ball roots has been a source of praise and criticism for Madonna as some think she merely ‘culturally appropriated’ the moves for commercial success. Considering Madonna’s inspirations have often been from the gay and/or African-American community and her support and recognition of both are well-known, it’s a flawed argument at best.
4. Hung Up (Johan Renck, 2005) and Sorry (Jamie King, 2005)
While less of a cheat than combining ‘Bedtime Story’ and ‘Nothing Really Matters,’ these two videos are pretty hand in hand. The end of ‘Hung Up’ is the immediate jumping off point for the beginning of ‘Sorry’ and they are true companion pieces. Starting with ‘Hung Up,’ Madonna, clad in a pink workout suit and massive boom box stretches and moves while dancers from around the city pop and lock and parkour their way to her as they all make their way to a club. Everything about this from the song to the dancing to Madonna’s look is flawless. In ‘Sorry,’ Madonna begins with international versions of saying she’s sorry and then picks up right where ‘Hung Up’ leaves off; exiting the club and getting into a van as they pick up various randos to continue their dance club night, ultimately ending up in cage match dance off and a roller rink.
3. Like a Prayer (Mary Lambert, 1989)
At the time, her most controversial music video ever. A black Jesus, burning crosses, racially-charged violence were all too much for Pepsi, who signed a fat contract with Madonna but then pulled her commercial once the video aired. Madonna kept the cash and the controversy pushed the song and video to the top of the charts. The video lands at #3 on my list for its brave and aggressive portrayal of religious and racial indignities and the ability and hope to rise above them. With her long, curly brown hair Madonna evokes a period before she was famous, an innocence that we hadn’t seen from her before. It pays off in a superbly directed video, concept and performance.
2. Justify My Love (Jean-Baptiste Mondino, 1990)
If The Night Porter had starred Marilyn Monroe it would be ‘Justify My Love.’ Madonna’s ode to 1960s French art porn, and shot by Mondino in a grainy, slightly sleazy style is a voyeur’s dream. She stars as a wanton woman wandering the halls of a hotel, passing open doors of sexuality of all kinds on display. Joining in the carnality, she cavorts with men, women, drag queens and her then model-boyfriend Tony Ward. It was also Madonna’s first video to be banned from television for its nudity and sexual content. Always the pioneer and innovator though, Madonna seized this moment to make it available for sale as a video single (oh the days before internet…), netting her a huge stash of cash. Point, Madonna.