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Probably around the Ray of Light era although I'm not really much of a fan.
Probably Ray Of Light but I have a campy liking for Vogue and Material Girl. Shut that door!
I admire her image changes and some of her music is okay but I've never been a huge fan. I was going to say I liked her early image because she was different from everything/everyone else that was happening at the time. But then I remembered Cindy Lauper who I feel made some great music, had a similarish image and got passed over because of Madonna to a certain extent.I've just reread that and I know what I mean but not sure anyone else will lol.
She also looked good in the "Rain" video:
Don't know about the best Phase She went a little side ways during the 90's But over 3 decades she has modified her image so many times some bad moves some good ones But for me it's her voice she has a nice set of lungs on her