Madonna starred in Who's That Girl

In 1987, Madonna starred in Who's That Girl, and contributed four songs to its soundtrack; including the title track and the U.S. number-two single, "Causing a Commotion".

In the same year, Madonna embarked on the Who's That Girl Tour. It marked Madonna' 1st conflict with the Vatican, as Pope John Paul II urged Italian fans not to attend her concerts.

Later that year, Madonna released a remix album of past hits, You Can Dance. In 1988, city officials in the town of Pacentro began to construct a 13-foot (4 m) statue of Madonna in a bustier. The statue commemorates the fact that her ancestors had lived in Pacentro.

In 1988, Madonna starred as Karen in a play by David Mamet called Speed-the-Plow.