Madonna's first transformation was revealed when she dropped the video for Papa Don't Preach. She had a date with controversy many times but this was the first big one.
Before the internet we didn't really see our favorite artists outside of concerts and award shows. For the True Blue album Madonna ditched the heavy jewelry and makeup, worked out like crazy and chopped off her hair. And everyone noticed. Including The Vatican. But it was the content of the song Papa Don't Preach that had the Vatican clutching their rosary's. The Pope felt that it glamorized teen girls getting pregnant. It didn't help that she dedicated the song to Pope John Paul II.
The Pope responded by urging his Italian followers to boycott her tour the following year.
Can't you just picture Madonna steepling her fingers at that news, laughing maniacally in her lair?
I mean that smile