"Papa Don't Preach" was, surprisingly, one of Madonna's more controversial singles. The lyrics suggested that Madonna's teenage character became pregnant with her boyfriend's child, and decided not to have an abortion and to "keep her baby." One would expect right-wingers to support this anti-abortion stance, but many criticized her anyway. A small group even made a response music video called "Madonna Don't Preach." Amidst all this controversy many ignored that the song (and video) could both be interpreted on a much simpler level -- Madonna simply wanted to date a guy her father didn't like, her "baby" being her boyfriend.

The song was one of Madonna's biggest hits, one of six singles she had spend multiple weeks at #1. The video is also one of her most compelling, skillfully telling the story of a conflicted teenager, juxtaposed with Madonna singing the song and dancing in a tight-fitting black outfit.

TRIVIA: In one quick shot of the video, Madonna's breast slips slightly out of her black outfit and for a split-second her nipple is visible. This slip-up was found accidentally while the editors were piecing together, as they just happened to freeze the video on the exact moment it occurs. Since it is so surreptitious, no effort was made to blur it out.