7. "Live to Tell" (1986)
Written and produced by Madonna and longtime collaborator Patrick Leonard, "Live to Tell" is the story of a woman facing a difficult decision. The song was written for the movie At Close Range, starring Sean Penn, Madonna's husband at the time. With this number-one ballad, Madonna emerged as more mature, abandoning the street urchin look for that of a grown-up.
8. "Papa Don't Preach" (1986)
Another one of Madonna's more serious ballads, the song tells the story of a pregnant teen who has decided to have her child and raise it with her boyfriend. You'd think such a heavy topic wouldn't fly as a pop song, but this was another number one for Madonna in the summer of 1986. Groups that had once condemned Madge now commended her for the song's antiabortion theme, although some were concerned that it glorified teen pregnancy.
9. "Open Your Heart" (1986)
In classic Madonna style, "Open Your Heart" was buoyed by a risqué video. In it, Madonna plays an exotic dancer who performs for a room that includes an underage boy. Plenty of people were outraged, but the song was another number-one hit.
10. "Who's That Girl" (1987)
Nominated for a Grammy, "Who's That Girl" sped to number one in the summer of 1987 when it appeared in the movie of the same name, starring Madonna. The movie didn't do so well, but the soundtrack went platinum. Other artists are included on the soundtrack, but this song and another Madonna hit, "Causing a Commotion," were the reasons most people picked it up.