Day 42 - Dress You Up (Madonna)

Remember when Madonna wasn’t quite yet the biggest star in the world? It was the summer of 1985, and the uptights were up in arms over her Penthouse photo shoot, and the writhing and wriggling wedding gown performance on the M.T.V. Video Awards, so as hot a July day as it was when she was performing this song live on the Live AID stage, she declared flatly, I ain’t taking shit off today! And I was watching it live, and I will never forget that moment. Madonna has been on my countdowns a few times, and rightly so. It’s truly impossible to pick a favorite. As with most songs, the draw of Dress You Up for me is about the time of my life to which it brings me back: I had just moved back to Lynbrook from the Poconos, first time truly declaring my independence from mom and dad. I lived in a room in Jan’s house and I rode a bike anywhere I needed to go. No car, no license. I remember listening to this song on cassette in a Walkman as I’d ride through familiar streets that no longer recognized me.