71. Madonna

Quick.  Now when did Madonna hit the wall?  Archaeologists will debate that for centuries to come regarding our current queen of cougars, but we can answer that question at least on a musical level.  She ceased being relevant (and hit the proverbial wall) in 2003, the year she unveiled American Life.

For the two decades before, Madonna pushed the envelope in every way possible.  The pop chameleon altered her style with the ease in with most people change a television channel.  It was seemingly effortless, and she was always ahead of the curve.  With American Life, Madonna produced another edgy video, this time tackling war as opposed to her usual taboos of religion and sex, however she did so at a time when American patriotism was at a high and the Dixie Chicks were ostracized for what in retrospect was a harmless remark about President Bush.  Amazingly, a woman who made a coffee table book featuring her floppy tits was now gun shy and pulled the video to release a non-descript one in its place.  Even worse, was the song itself with featured a thirty second rap, that Madonna was not able to deliver with any ounce of credibility.  Sure, Madonna went back to a proven formula and did have hits again (and she may likely have more), but in 2003 she went from the Material Girl to Crazy Rappin’ Granny, but even worse a conformist and a leader no more.