There were definitely a lot of firsts and lasts for Madonna on the “Who’s That Girl” tour, from which this performance is taken: it was her first world tour, and the last time she was greeted quite so rapturously in Italy. It was the first time she used elaborate set pieces, and it was the last time they were so unformed and unrelated. It was the first time she was quite such a dominant presence on stage, and the last time she used purely live vocals.
It was, by her own admission, the first time she realized how big everything had gotten. And it was the last time she looked like she was really having fun.
“Into the Groove”, Torino, Italy, Sep. 4th 1987. Enjoy.