Sean Penn and Madonna

At the time, Madonna was sort of half-dating Prince and she also had a crush on Keith Carradine. She cast him in the video as an excuse to make out with him. From the beginning, the relationship was tempestuous. He was threatened by her highly sexual image and obstinate focus on career. They knew that if word got out that they were engaged, there would be a media frenzy. Penn told his betrothed not to tell anybody except for Rosanna Arquette.