Madonna's “This Used to Be My Playground” became her tenth U.S. No. 1 hit. It reached No. 3 in the UK and was from the film “A League Of Their Own”. The song also reached No. 1 in Canada, Italy, Mexico and Sweden.
Madonna během koncertu v Pontiac Silverdome zastavila vystoupení, aby se omluvila 42 000 fanouškům za své předchozí označení rodného města Bay City v Michiganu za „smelly little town“.
Madonna reached No. 1 on the U.S. Billboard Hot 100 with “Who's That Girl”, her sixth U.S. No. 1 single and also a No. 1 hit in the United Kingdom. It was a Spanish-English song with the refrain “¿Quién es esta niña?” and the title track of the soundtrack album to the comedy film of the same name, in which Madonna starred alongside Griffin Dunne.
Madonna's album True Blue reached No. 1 on the US albums chart, while the single "Papa Don't Preach" began a two-week run at No. 1 on the US singles chart.
Madonna appeared in the film "Shanghai Surprise", which flopped at the box office and was harshly rejected by critics. The film was produced by George Harrison's HandMade Films, and Harrison said of Madonna that she had no sense of humor, which was unfortunate for a comedy.