Year: 1990
Director: Jean-Baptiste Mondino
Why: If you're under 25 and don't understand why so many people respect Madonna for pushing the envelope for gay rights and freedom of expression before it was hip to do so it would be hard to explain what MTV or the rest of cable television was like before "Justify My Love."  The video featured overtly sexual imagery between Madonna, a woman in drag, her boyfriend in the video (Tony Ward, also her real life beau at the time) and male drag queens as well as exploring the hardly discussed topics of bisexuality and S&M.  The video created a furor (Madonna was interviewed on Nightline by Ted Koppel about it) and would have made the all-time list for the conversation it created in the United States alone. And yet, as a piece of film "Justify My Love" is utterly exceptional.  Influenced by 1960's black and white European films, "Love" is a true artistic achievement in Madonna's videography. It asks the viewer to accept Madonna's world without judgement and not to force her to "justify her love." It opened up a whole new window for creative expression on television and in music videos and pop culture has never been the same since.

Watch it here.