Year: 1990
Director: David Fincher
Why: Granted, Fincher doesn't reach the artistic heights of "Oh, Father" or "Express Yourself," but the Academy Award nominated filmmaker may have no scrap of film more iconic in his career than the video for "Vogue."  Art directed to a retro 30's and 40's vibe, the video turned dance music on its head (just in time for a new decade) and is still instantly recognizable to different generations around the globe over 20 years later. What's truly groundbreaking about it might not be apparent to the average viewer, but the cross cutting at the end with the fade outs on each cut (the dancers) was revolutionary at the time and has been ripped off every since.  And while it may feel a tad dated more than some of the videos lower on the list its mix of drag queen voguing, overt sexuality and confidence still make it hard for even the most conservative critic to resist.

Watch it here.