The way I see it is this. Madonna is ruining her legacy because she's trying to stay relevant in a music genre that primarily values young and good looking people. Were she a jazz or blues singer where aging or youthful looks isn't such a big issue (because of the very nature of it), she wouldn't look like this. So she went from a torch-bearer to someone who's trying to keep up with the new kids. She should have dignifiedly retired right after Confessions on a Dancefloor. Everything afterwards is a downward spiral that brought her to this point.